JPS61282390A - S-neuraminic acid derivative - Google Patents

Abstract

NEW MATERIAL:A compound shown by the formula I [R1 and R2 are acyl or hydrogen; R3 is acyl; R4 is H or lower alkyl; R5 is H or alkaliine (earth) metal, etc.] and its salt. EXAMPLE:Allyl 2-acetamido-3,4-di-O-acetyl-6-bromo-2,6-dideoxy-beta-D-gluc-opyranosi de. USE:An intermediate for synthesizing an S-containing ganglioside compound showing the same biological activity as that of naturally occurring ganglioside. The compound can be synthesized without losing steric specificity. PREPARATION:Firstly, a compound shown by the formula II [R1' and R2' are acyl; R4' is lower alkyl; M is alkaline (earth) metal] is reacted with potassium thiocetate in a solvent, the prepared compound shown by the formula III is reacted with an alkoxide, to give a compound shown by the formula IV. Then, this compound is reacted with an alkyl halide, and the reaction product is reacted with an alkoxide to give a compound shown by the formula V, which is reacted with an alkali to give a compound shown by the formula I wherein R1, R2 and R4 are H and R5 is alkali.

Description

Detailed Description of the Invention <Industrial Application Field> The present invention is based on the general formula (wherein R1 and - represent an acyl group or hydrogen, R3 represents an acyl group, R4 represents hydrogen or a lower alkyl group, and R5 represents Hydrogen, alkali metal, alkaline earth metal, alkyl (in the formula, R
6 is hydrogen, allyl or lower alkyl group.

R7 means acylamino or hydroxyl group. ) means a group represented by The present invention relates to a novel S-neuraminic acid derivative represented by the following formula and a salt thereof.

<Conventional technology> N-acetylneuraminic acid (hereinafter referred to as NhNl).

) exists on the cell surface as a component of gangliosides, and has attracted attention as a unique component responsible for the biological functions of gangliosides, such as nerves, immunity, cancer, inflammatory bidifferentiation, and various glue receptor functions.

In the production of ganglioside derivatives from NANA, NANA is chemically unstable.

There were problems such as difficulty in selectively maintaining the stereospecificity of NANA. Furthermore, natural gangliosides themselves are easily degraded by enzymes such as neuraminidase, which poses a problem in terms of sustainability of activity.

<Problem to be solved by the invention> As a result of intensive studies to eliminate the above-mentioned drawbacks, the inventor has found that A.
&Complete the present invention by discovering that the above drawbacks can be overcome by introducing a sulfur atom into ANA, and that gangliosides containing a sulfur atom can have an activity equivalent to that of the natural type 〇<Structure of the invention> The present invention relates to compounds of formula (1).

In the formula, the lower alkyl group is methyl or ethyl.

Examples include propyl, isopropyl, butyl groups, etc.

Examples of the alkyl group include hexyl, heptyl, dodecyl, pentadecyl, and octadecyl groups in addition to the lower alkyl groups mentioned above.

The compound of formula (1) of the present invention is a new compound and can be produced by the method shown below.

(In the formula, the 9 spots and the bow represent an acyl group, the melon represents a lower alkyl group, 1M represents an alkali metal or an alkaline earth metal, and R
3 is the same as above. ) That is, the compound of formula (1) can be obtained by reacting the compound of formula (1) with potassium thioacetate in a solvent such as dichloromethane. By reacting this with an alkoxide such as sodium methoxide, a compound of formula (5) in which in formula (I) is an alkali metal or alkaline earth metal, - is a lower alkyl group, and R1 and & is an acyl group can be obtained. Obtainable.

From the obtained compound of formula (11/), the following a
Various compounds of the present invention can be produced by the methods of ) and b).

&) (In the formula, m*m, R3, and 0 are the same as above.

Thief means an alkyl group. ) That is, by reacting the compound of formula 1 (g) with an alkyl halide in a solvent such as dimethylformamide, the compound of formula (t) can be obtained.
can be obtained. This is reacted with an alkoxide such as sodium methoxide to obtain a compound of formula (6), and by reacting this with an alkali such as potassium hydroxide, in -<(I), R1°- and - are hydrogen. Compounds of formula (2) which are alkyl groups can be obtained.

(z) g7 LX) to 7(
In the formula, the first term means an acyloxy or acylamino group +
me m, R3, R4, - and R7 are the same as before.

) That is, the compound of formula (4) can be obtained by reacting the compound of formula (2) with a compound represented by the formula (wherein Rs and 弼 are the same as above) in a solvent such as dimethylformamide. By reacting this with a flukoxide such as sodium methoxide, a compound of the formula (transformation) 9 is obtained.Next, by reacting with an alkali such as potassium hydroxide, a compound of the formula (r) is obtained. , R11 and Mari are the same as above.) A compound of formula (1) can be obtained.

cancer from the compound of the present invention thus obtained.

Examples of methods for producing glioside include the following.

That is, the allyl group is removed from the compound of formula (1) in which & is an allyl group by acetolysis or other methods. The final compound, S-containing ganglioside, can be produced by condensing the obtained compound with saccharides such as glucose or ceramide, etc. using a known glycoside synthesis reaction. By using this, S-containing gangliosides can be produced without losing the stereospecificity of NANA. Furthermore, S-containing gangliosides may have effects equivalent to natural gangliosides.

It may also be stable against enzymes such as neuraminidase.

Therefore, the compounds of the present invention are useful as intermediates for the synthesis of S-containing ganglioside compounds that are expected to have excellent biological activity.

Reference example methyl 5-acetamido-4, 8,9-tetra 0
-acetyl-2-8-acetyl-8,5-dideoxy-
2-Thio D-glycero α-D-galacto-2-7 Nurovyranosonate methyl 5-acetamido-4,7,8,9-tetra-0
-acetyl-8,5-dideoxy-D-gly74-α-
Dissolve 8.89% of D-galacto-2-nonurovirasonate in 50% of acetyl chloride, and add hydrogen chloride gas to -40°C.
After bubbling into the reaction solution for 15 minutes, the flask was sealed and left in a dark place for 2 days. After confirming the completion of the reaction by thin layer chromatography (hereinafter referred to as TLC), acetyl chloride was distilled off under reduced pressure at 80° C., and azeotropic distillation was carried out eight times with dichloromethane to obtain a silica. After adding anhydrous calcium sulfate to this, 80 g of dry dichloromethane was added and stirred, and then 8.56 g of potassium thioacetate was added and stirred overnight at room temperature. T.L.G.
After confirming the completion of the reaction, one reaction solution was concentrated under reduced pressure. The obtained silica was purified by column chromatography (elution solvent: chloroform-methanol (100:1)) to obtain 8.429 of the title compound (hereinafter, compound A) as an amorphous. Melting point 74-76°C. [α) D-15,6°
(c-〇,)5. Chloroform) 0 Elemental analysis C2zHstNO13S Calculated value C48,08, H5,69, N 2.5B Actual value 048.08. H5,81,N 2.46 Example 1 Methyl 5-acetamido-4,7,8,9-tetra-0
- Acetyl-8,5-dideoxy-2-thio D-glycerol α-D-galacto-2-nonulopyranosonate Ha salt Compound A100ss+ was added with anhydrous calcium sulfate, dissolved in 8 g ILl of anhydrous methanol, and heated at -40°C. Stirred.

Sodium 8.9 s9 was previously dissolved in anhydrous methanol, /
The solution dissolved in L/1gLt was added dropwise to the reaction solution and stirred at -40°C for 40 minutes. After confirming the completion of the reaction by TLc, the mixture was concentrated under reduced pressure at 20° C. to quantitatively obtain the title compound (hereinafter referred to as compound B) as a silica. (α)D
"11.65° (a-o, s, methanol, le) Example 2 (1) Methyl (n-hexyl-5-acetamide-4
), 8,9-tetra-0-acetyl-8,5-dideoxy-2-thio D-glycero α-D-galacto-2
-7 Nuroviranoside) onate Compound B obtained in Example 1 was thoroughly dried, then dissolved in dry dimethylformamide 2-, and stirred at 0°C. 20 m9 of 1-promo n-hexane previously dissolved in dry dimethylformamide 1- was added dropwise to the reaction solution pile, and the mixture was purged with nitrogen.

The mixture was stirred at room temperature for one day. After confirming the completion of the reaction using TLG, dimethylformamide was distilled off under reduced pressure, azeotropically distilled several times with toluene, and then extracted with chloroform.

The chloroform layer was washed with water, dehydrated with anhydrous sodium sulfate, filtered through cotton to remove sulfuric acid, and washed with chloroform. The filtrate and washing liquid were combined and concentrated under reduced pressure. Column chromatography (elution solvent;
Purification with chloroform-methanol (150:1) gave the title compound (below).

Compound C) 97.5'l'9 was obtained as amorphous.

Melting point 118-120°Co (α), +28.89°(
c-06749, chloroform).

Elemental analysis (lzaHuOIzNS calculated value G 52.78. H6,98, N 2.8
7 Actual measurement value C52, 51, H6, 96, N 2.86 (
2) Methyl (n-hexyl-5-acetamide-8,
5-dideoxy-2-thio D-glycerol α-D-galacto-2-nonuroviranoside)onate compound 0'1f3q was dissolved in 2 g Lt of anhydrous methanol and stirred at -10°C. A catalytic amount of sodium methoxide was added, the temperature was returned to room temperature, and the mixture was stirred for 4 hours. After confirming the completion of the reaction with TIC, neutralize with IR-120 (cation exchange resin), remove the resin with cotton filtration, wash with methanol, and combine the filtrate and washing liquid to obtain the title compound (hereinafter referred to as compound). D)
40.0 .mu.m was obtained as amorphous. Melting point 154-1
56°C0 [α].

+51.20° (c-0,500, chloroform-methanol (1:1)).

Elemental analysis Cx5Hs30sNS Calculated value G 51.05. H7,85,N 3.3
1 Actual measurement value C51, 22, H7, 91, N 3.28 (
3) n-hexyl 5-acetamido-8,5-dideoxy-2-thio D-glycero α-D-galacto-2-
7 Nurovyranosido, quasi, compound D25 is dissolved in dioxane 2-.

While stirring at 0°C, 1.5-liter of 0.2N aqueous potassium hydroxide solution was added dropwise. Thereafter, the mixture was returned to room temperature and stirred for 4 hours. After confirming the completion of the reaction with TLe, pip with Amberly IR-120 (cation exchange resin), which had been washed with water in advance.
) (around 6, and the resin was removed by cotton filtration and washed with water. The filtrate and washing liquid were combined and freeze-dried as they were to quantitatively obtain the title compound as an amorphous substance. Melting point: 139~
141°C0 [α] +88.58° (c-o, 262
．． Dioxane-water (], : 1)).

Elemental analysis (47) 13108NS Calculated value C49,86,I(7,63,N 3.42 Actual value C49,58,H7,82,N 133 Example 8 (1) Methyl (n-dodecyl-5-acetamide-
4,7,8,9-tetra-0-acetyl-3,5-dideoxy-2-thio D-glycero α-D-galacto-
2-nonulopyranosonate compound 8180■ and 1-bromododecane 127.2"
9 was used to react in the same manner as in Example 2 (1) to obtain the title compound (hereinafter referred to as compound -) 200+119 as an amorphous. Melting point 48~50°Co (α) 0+ 21
．． 85° (C-0,693, ritroform).

Elemental analysis C5zHsaNO+zS Calculated value C56,87, H7,90, N 2.07 Actual value C56,72, H8,15, N 2.06 (2)
Methyl (n-dodecyl-5-acetamide-8,5-
dideoxy-2-thio D-glycerol α-D-galacto-2-7nurovyranoside)onate compound E120■ was reacted in the same manner as in Example 2 (2) to quantitatively obtain the title compound (hereinafter, compound F) as an amorphous. Obtained. Melting point 88-90'C8 [α), +41.6
8°(C-0,9131 Chloroform-methanol (1
:1)).

Elemental analysis Ox 4 ) h s Os NS calculated value C
56,78,H8,98,N 2.76 actual value C56
,60,H9,25,N 2.70(3) 5-acetamido-8,5-dideoxy-g-S-dodecyl-2-thio D-glycerol α-D-galacto-2-7 neuroviranosonic acid Compound? 50■ was reacted in the same manner as in Example 2 (3) to quantitatively obtain the title compound as amorphous.

Melting point: 149-151°C. [α]. +18.870 (C-
0,498, dioxane).

Elemental analysis C23H4308NS Calculated value C55,96, H8,78, N 2.84 Actual value 055.71. H8,98,N 2.78 Example 4 (1) Methyl (n-octadecyl-5-acetamide-4,), 8,9-tetra-O-acetyl-8,5-
D-2-thio D-glycero-α-D-galacto-
2-7 Nuroviranoside) onate compound 8144 and 1-promooctadecane 185.01119 were reacted in the same manner as in Example 2(1) to obtain the title compound (hereinafter referred to as compound G) 143.41119 as a silica. [α]
. +21.8° (C-0,48, chloroform).

Elemental analysis (: Calculated value as 3aHasO1zNS C
60,06,H8,62,N 1.84 Actual value C60
,28,H8,90,N 1.85(2) Methyl
(n-octadecy#-5-acetamido-8,5-dideoxy-2-thio D-glycerol α-D-galacto-2
-7 Nuroviranoside) onate compound G148119 was reacted in the same manner as in Example 2 (2) to quantitatively obtain the title compound (hereinafter referred to as Compound H) as an amorphous. Melting point 104-106"C0 [α].

+41.9° (co, ao, chloroform-methanol (1:1)).

Elemental analysis Os o m 70a N S calculated value C6
0.88, H9, 71, N 2.37 actual value C60,
56,H9,85,N 2.26(3) 5-acetamido-3,5-dideoxy-2-S-octadecyl-2-thio D-glycero α-D-galacto-2-nonulopyranosonic acid compound H3O1119 was reacted in the same manner as in Example 2 (3) to quantitatively obtain the title compound as amorphous.

Melting point 124-126°C. [α), +12.70' (
Ci-0,181, dioxane-water (1:1)).

Elemental analysis C29C29Hs50 Calculated value C60,28, H9,59, N 2.42 Actual value C60,11, H9, F8. N 2.42 Example 5 (1) Methyl 2,8.4-triloacetyl-
6-s-(methyl 5-acetamide-4,7,8,9-
Tetra-0-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-7-nulopyranocylonate)-6-thio-2-D-gulfpyranoside Compound 819
2rn9 was dissolved in dry dimethylformamide 2- and 0°
The mixture was stirred at C. Methyl 2,3.4-triloacetyl-6-bromo-6-zooxy-α-D-glucopyranoside 208.51s9 was previously dissolved in dry dimethylformamide 2- and added dropwise to the reaction solution. Then under nitrogen replacement.

The mixture was stirred at 60°C for 1 day. After confirming the completion of the reaction by TLO, the solvent was distilled off under reduced pressure at 60° C., and the mixture was azeotropically distilled several times with toluene. Extraction was performed with chloroform, and the chloroform layer was washed with water and dehydrated with anhydrous sodium sulfate. Remove sodium sulfate by cotton filtration.

Washed with chloroform. The filtrate and washing liquid were combined and concentrated under reduced pressure. The obtained silica was purified by column chromatography (elution solvent: chloroform-methanol (zso:x)) to yield the title compound (below).

266.4'9 of compound J) was obtained as amorphous.

Melting point 104-106°C. [α), +77.2°(c
-5,83, chloroform).

Elemental analysis Cs5Hu02oNS Calculated value 050.71. H2, 45, N 1.79
Actual value C50, 50, H2, 63, N 1.75 (2
) Methyl 6-3-(methyl 5-acetamide-8
,5-dideoxy-〇-glycero-α-D-galaketo-
2-nonulopyranocilone))-6-thio-α-kuglucopyranoside compound J235■ was dissolved in 5 tL of anhydrous methanol and stirred at -1θ°C. A catalytic amount of sodium methoxide was added, the temperature was returned to room temperature, and the mixture was stirred for 8 hours. After confirming the completion of the reaction with TLC, use Amberley+4R-120 (@ion exchange resin)
After neutralizing with water and removing the resin with cotton filtration, the mixture was washed with methanol. The filtrate and washing liquid were combined and concentrated under reduced pressure to quantitatively obtain the title compound (hereinafter referred to as compound K) as an amorphous substance. Melting point 127
~129℃. [α]. +sa, as°((j-1,84
2, chloroform-methanol (1:1)).

Elemental analysis c1oHsso1aNs Calculated value C44,27, H6,45, N 2.72 Actual value C44,08, H6,59, N 2.70 (8)
Methyl 6-8-(5-acetamido-8,5-dideoxy-2-thio D-glycerol α-D-galacto-2
-Nonupyranosonic acid)-α-D-glucopyranoside compound (150 μm) was dissolved in dioxane 3-.

0.2N potassium hydroxide aqueous solution 2 while stirring at 0°C.
- was added dropwise. The mixture was returned to room temperature and stirred for 3.5 hours.

After confirming the completion of the reaction with TLC, plating with Amberlite IR-120 (cation exchange resin) which had been washed with water in advance.
It was prepared around H6. The resin was removed by cotton filtration and washed with water. The filtrate and washing solution were combined and directly freeze-dried to obtain the title compound in an amorphous form quantitatively. Melting point 184
~186℃.

[α]. +80.81° (c-0,767, dioxane-water (1:1)).

Elemental analysis CtaHstOuNS Calculated value C'43.11. H6, 28, N 2.7
9 Actual value C42,85, H6,51, N 2.68 Example 6 (1) Methyl 2,8.4-)di-0-acetyl-
6-S-(methyl 5-acetamide 4.7.8.9-
Tetra-0-acetyl-8,5-dideoxy-D-glycero-α-D-galacto-2-nonuroviranocilone)
)-6-thio α-D-galactopyranosi compound 811
0■ and methyl 2,3,4-tri0-acetyl-
The reaction was carried out in the same manner as in Example 5(1) using 121.2 .mu. of 6-promo-6-zooxy-.alpha.-D-galactopyranosi) to obtain 118.4 .mu. of the title compound (hereinafter referred to as compound L) as an amorphous.

Melting point 100-102°C. [α), +68.01° (c-
1,016, chloroform) 0 Elemental analysis 033H4702ONS Calculated value C50, F1. H2, 45, N 1.79
Actual value Q 50.52. H2,62,N 1.7
1(2) Methyl a-S-(methyl 5-acetamido-8,5-dideoxy-D-glycero-α-D-galacto 2-nonuroviranocylonate)-6-thio α-lactopyranoside compound L100119 as an example The reaction was carried out in the same manner as in 5(2) to quantitatively obtain the title compound (hereinafter referred to as compound M) as an amorphous. Melting point: 189-141°C8 [α]. +
76.44° (C-0,692, chloroform-methanol (1:1)).

Elemental analysis C19Ha3013N9 Calculated value 044.27. H6, 45, N 2.72
Actual value 04425. H6, 69, N 2.83 (
3) Methyl 6-3-(5-acetamide-8,5-
Sideoxy-D-glycero-α-D-galacto-2-nonuroviranosonic acid)”)-6-thio-α-cougalactopyranoside compound M35■ was reacted in the same manner as in Example 5 (8) to obtain the title compound. was quantitatively obtained as amorphous.

Melting point: 174-176°C. [α)n + 74-6 ao
(c-0, ,975, dioxane-water (1:1)).

Elemental analysis Kaisei 1013NS Calculated value C48,11,H6J8. N 2.79 Actual value 043.06. H6,88,N 2.75 Example 7 (1) Allyl 2,3.4-)LeeO-acetyl-6-
Promo 6-zooxy-β-D-glufuviranoside Allyl β-D-glucopyranoside 920 μg was dissolved in 1Qg 4t of dry pyridine and stirred at 0°C. In this solution, 1.67 g of carbon tetrabromide and 1 gram of triphenylphosphine were added.
．． 652 was added and then stirred at room temperature. After about 2 hours, carbon tetrabromide ZOO■ and triphenylphosphine 2
00g59 was added and the mixture was further stirred at room temperature for about 2 hours. After confirming the completion of the reaction at TI, C, methanol was added and the reaction solution was concentrated under reduced pressure and azeotroped several times with toluene. The obtained silica was purified by column chromatography (elution solvent: croseform-methanol AI (50:1)) to obtain allyl 6-promo 6-zooxy-β-D-glucopyranoside 480119 as a silica. 850 vq of this syllabi was dissolved in 3 d of dry pyridine, and 1.5 ml of acetic anhydride was added while stirring at 0°C. After returning to room temperature and stirring for about 2 hours, completion of the reaction was confirmed by TLC, and methanol was added. The reaction solution was distilled off under reduced pressure, azeotropically distilled with toluene several times, and extracted with chloroform. The chloroform layer was washed with 2N hydrochloric acid, an aqueous solution of sodium carbonate, and water in that order, and dehydrated with anhydrous sulfuric acid. Sodium sulfate was removed by cotton filtration and washed with chloroform. The filtrate and washing liquid were combined and concentrated under reduced pressure to quantitatively obtain the title compound (hereinafter referred to as compound N) as crystals. Melting point: 109-111°C.

(α), −7,18° (C-1,017, chloroform).

Elemental analysis 1:5s) tuosBr Calculated value C44,02,H5,1? Actual value C4 & 96. )15.20(2) Allyl
2,8.4-) di-0-acetyl-6-s-(methyl 5-acetamide-4,7,8,9-tetote O-acety/I/-3,5-dideoxy-D-glycero-α -D
-galacto-2-nonuropyranocylonate)-6-thiohβ-D-gulfvira/cyto compound B156.1119
and Compound N18G119 were reacted in the same manner as in Example 5(1) to obtain the title compound (hereinafter referred to as Compound 0) 178.
1■ was obtained as amorphous. Melting point 89-91"C0
[α]. +25.17° (Cj-0,564, chloroform).

Elemental analysis Cx5H4e02 (INS calculated value C50JO, H5,91, H1,68 actual value
G 50.19. H5,98,N L67(1)
Allyl a-S-(methyl 5-acetamide-3,5
-dideoxy-D-glycero-α-D-galacto 2-
Nonulopyranocylonate) -a-thio-β-loglucopyranoside Compound 0 12119 was reacted in the same manner as in Example 5(2) to obtain the title compound (hereinafter referred to as Compound P) 69.1■ in an amorphous form. Melting point 119-121'c.

[α), +25.91° (0-0,355, methanol).

Elemental analysis c2tHsso+sNs Calculated value 046.57. H6,51,N2.59
Actual value 046.88. H6, 55, N 2.51
(4) Allyl 6-3-(5-acetamide-8,5-
Dideoxy-D-glycero-α-D-galacto-2-nonuroviranosoni, quasi, do)-6-thio β-D-glufviranoside compound p35+ag was reacted in the same manner as in Example 5 (3) to quantitatively convert the title compound into an amorphous state. I got it.

Melting point 161-16.3°C0 [α), +29.94° (
c-0,854, water).

elemental analysis). Hss013NE3 Calculated value 045.54. H6, (1, N 2.66
Actual value C45.51, H6.4B, N 2.69
Example 8 (1) Allyl 2-acetamide-3,4-di0-
a7-thyru-6-promo2,6-sideoxy-β-D-
Glucobyranoside allyl 2-acetamido-β-D-glucopyranoside 1
．． 19. A reaction was carried out in the same manner as in Example 7 (1) using 1.58 g of carbon tetrabromide and 1.57 g of triphenylphosphine to obtain allyl 2-acetamido-6-bupmo-2,6-sideoxy-β-D-gulfpyrano. Cyto 590■ was obtained as a sill. This is 5801S
9 and acetic anhydride in the same manner as in Example 7(1), the title compound (hereinafter referred to as compound Q) was quantitatively obtained as crystals. Melting point: 174-176°C.

[α) D-+, 5o0 (C-2,22, chloroform)
.

Elemental analysis C*5lbxO7NBr Calculated value C44, IJ, H5,48, N 3.48
Actual measurement value C44, 15, H5, 40, N 1119 (2
) Allyl 2-acetamido-8,4-di-0-acetyl-2-deoxy-6-3-(methyl 5-acetamido-
4789-Tetra-0-acetyl-8,5-dideoxy-D-glycero-α-D-galacto-2-nonuroviranocilone))-6-thio-β-loglucopyranoside Compound B1 Furo, 8■ and Compound q202゜1'119
was reacted in the same manner as in Example 5 (1) to produce the title compound (hereinafter).

Compound R) 240q was obtained as amorphous.

Melting point 123-125°C. [α]. +27.91'(C-
0,695, chloroform) 0 Elemental analysis C35H500111N2S calculated value 050
．． 85. H6,04,N 3J6 actual value C5Q,
11. H6,al, N 3.27(3) Allyl 2-acetamido-2-deoxy-6-8-(methyl
5-A7tamido 8,5-dideoxy-D-glycero-
α-D-galactose 2-7 neuroviranocilone))-6
-thio-β-loglucopyranoside compound R210■ was reacted in the same manner as in Example 5 (2) to quantitatively obtain the title compound (hereinafter referred to as compound S) as an amorphous. Melting point: 210-212°C.

[α]. +22.08° (c=1.354.methanol).

Elemental analysis c2+HasOxzNzS Calculated value 046.66, H6,71,N 5.18
Actual measurement value C46,63,H6,58,N 5.06 (4
) Allyl 2-acetamido-2-deoxy-6-S-(
S-acetamido-8,5-dideoxy-D-glycero-
5100ml of α-D-galacto-2-7-nulopyranosonic acid)-6-thio-β-loglucopyranoside compound was reacted in the same manner as in Example 5(3) to obtain the title compound 98119 as amorphous.

Melting point 208-210°C0 (α), +86.02° (c
−0, lJI, water).

Claims (1)

[Claims] General formula ▲ Numerical formula, chemical formula, table, etc. ▼ [In the formula, R_1 and R_2 are an acyl group or hydrogen, R_
3 is an acyl group, R_4 is hydrogen or a lower alkyl group,
R_5 is hydrogen, alkali metal, alkaline earth metal, alkyl group, or formula ▲ Numerical formula, chemical formula, table, etc. ▼ (In the formula, R_6 is hydrogen, allyl, or lower alkyl group,
R_7 means acylamino or hydroxyl group. ) means a group represented by ] and its salts