JPH0631291B2 - S-neuraminic acid derivative - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION <Industrial field of application> The present invention has the general formula (I) [In the formula, R ₁ and R ₂ are an acyl group or a hydrogen group, R ₃ is an acyl group, R ₄ is a hydrogen or a lower alkyl group, and R ₅ is a formula. (Wherein, R ₆ is hydrogen, an allyl group or a lower alkyl group, R ₇
Means an acylamino group or a hydroxyl group), and a novel S-neuraminic acid derivative represented by the formula: and a salt thereof.

<Problems to be Solved by Conventional Techniques and Inventions> N-acetylneuraminic acid (hereinafter referred to as NANA) exists on the cell surface as a component of ganglioside, and has a biological function of ganglioside, that is, a nerve. Immunity,
It has attracted attention as a unique component responsible for cancer, inflammation, differentiation and various receptor functions.

However, in the production of a ganglioside derivative from NANA, NANA is chemically unstable,
There is a problem that it is difficult to selectively retain the stereospecificity of NANA. In addition, natural ganglioside itself is easily decomposed by enzymes such as neuraminidase, and there is a problem in that the activity is persistent.

<Means for Solving Problems> Therefore, as a result of earnest studies to solve the above-mentioned drawbacks, the present inventors have solved the above-mentioned drawbacks by introducing a sulfur atom into the bond of the 2-position substituent of NANA. It was found that the ganglioside containing a sulfur atom can have an activity equivalent to that of the natural type, and completed the present invention.

Therefore, the present invention provides the S-neuraminic acid derivative represented by the general formula (I) and a salt thereof.

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

(Wherein R ₁ ′ and R ₂ ′ are acyl groups, R ₄ ′ is a lower alkyl group, M is an alkali metal or alkaline earth metal, and R ₃ is the same as described above). The compound of () can be reacted with potassium thioacetate in a solvent such as dichloromethane to give the compound of formula (III), and then the compound of formula (IV) can be obtained by reacting it with an alkoxide such as sodium methoxide. .

(In the formula, R ₇ ′ means an acyloxy or acylamino group, and R ₁ ′, R ₂ ′, R ₃ , R ₄ ′, R ₆ and R ₇ are the same as the above), that is, the compound of the formula (IV) Formula in a solvent such as dimethylformamide (In the formula, R ₆ and R ₇ ′ are the same as above) to form a compound of formula (V), which is then reacted with an alkoxide such as sodium methoxide to form a compound of formula (VI) The compound of the formula (VII) can be obtained by forming a compound and further reacting it with an alkali such as potassium hydroxide.

The compound of the present invention thus obtained can be converted into a ganglioside as follows. For example, formula (VII)
S-containing ganglioside is produced by removing an allyl group from a compound in which R ₆ is an allyl group by acetolysis or other method, and then condensing it with a sugar or ceramide using a known glycoside synthesis reaction. be able to.

<Effects of the Invention> By using the compound of the present invention, an S-containing ganglioside can be produced without losing the stereospecificity of NANA. Also, S-containing gangliosides can have the same effects as natural gangliosides and can be stable against enzymes such as neuraminidase. Therefore, the compound of the present invention is a useful compound as a synthetic intermediate for an S-containing ganglioside compound which is expected to have excellent biological activity.

Reference Example Methyl 5-acetamide-4,7,8,9-tetra-0-acetyl-2-S-acetyl-3,5-dideoxy-2-thio-D-glycero-α-D-galact-2-no Nuropyranosonate methyl 5-acetamide-4,7,8,9-tetra-0-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonuropyranosonate 3.3 g of acetyl Dissolve in 50 ml of chloride and add hydrogen chloride gas at -40 ° C for 15
After blowing for 1 minute into the reaction solution, the flask was sealed and left in the dark for 2 days. Thin layer chromatography (hereinafter TL
After confirming the completion of the reaction in C), add acetyl chloride at 30 ° C.
The solvent was distilled off under reduced pressure and azeotropically distilled with dichloromethane three times to obtain syrup. After adding anhydrous calcium sulfate to this, add 30 ml of dry dichloromethane and stir potassium thioacetate.
3.56 g was added and the mixture was stirred at room temperature overnight. After confirming the completion of the reaction by TLC, the reaction solution was concentrated under reduced pressure. The obtained syrup was subjected to column chromatography (elution solvent: chloroform-
Purification with methanol (100: 1) gave 3.42 g of the title compound (hereinafter, compound A) as an amorphous substance. Melting point 74-76 [deg.] C. [Α] _D -15.6 ° (C = 0.775, chloroform).

Elemental analysis C ₂₂ H ₃₁ NO ₁₃ S Calculated value C 48.08, H 5.69, N 2.55 Measured value C 48.03, H 5.81, N 2.46 Example 1 Methyl 5-acetamide-4,7,8,9-tetra-0-acetyl -3,5-dideoxy-2-thio-D-glycero-α
-Na salt of D-galacto-2-nonuropyranosonate To 100 mg of Compound A, anhydrous calcium sulfate was added, dissolved in 3 ml of anhydrous methanol, and stirred at -40 ° C. A solution prepared by previously dissolving 3.9 mg of sodium in 1 ml of anhydrous methanol 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, compound B) as a syrup. ▲ [α] ²⁵ _D ▼ + 1.65 ° (C = 0.5,
Methanol) Example 2 (1) Methyl (n-hexyl-5-acetamide-4,7,8,9
-Tetra-0-acetyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonuropyranoside) onate The compound B obtained in Example 1 was thoroughly dried and then dried dimethylformamide. It was dissolved in 2 ml and stirred at 0 ° C.
A solution prepared by previously dissolving 20 mg of 1-bromo-n-hexane in 1 ml of dry dimethylformamide was added dropwise to the reaction solution, and the mixture was stirred at room temperature for 1 day under nitrogen substitution. After confirming the completion of the reaction by TLC, dimethylformamide was distilled off under reduced pressure,
After azeotroping with toluene several times, it was extracted with chloroform. The chloroform layer was washed with water, dehydrated with anhydrous sodium sulfate, filtered to remove sodium sulfate by filtration with cotton, and washed with chloroform. The filtrate and washings were combined and concentrated under reduced pressure. The obtained syrup is purified by column chromatography (elution solvent: chloroform-methanol (150: 1)),
97.5 mg of the title compound (hereinafter, compound C) was obtained as an amorphous substance. Melting point 118-120 [deg.] C. [Α] _D + 23.89 ° (C = 0.749, chloroform).

Elemental analysis C ₂₆ H ₄₁ O ₁₂ NS Calculated value C 52.78, H 6.98, N 2.37 Measured value C 52.51, H 6.96, N 2.36 (2) Methyl (n-hexyl-5-acetamide-3,5-dideoxy-2-) Thio-D-glycero-α-D-galacto-2-nonuropyranoside) onate Compound C73 mg was dissolved in anhydrous methanol 2 ml and -10 ° C.
It was stirred at. A catalytic amount of sodium methoxide was added and the mixture was returned to room temperature and stirred for 4 hours. After confirming the completion of the reaction by TLC, the reaction mixture was neutralized with Amberlite IR-120 (cation exchange resin), the resin was removed by cotton filtration, and the mixture was washed with methanol, and the filtrate and the washing liquid were combined to give the title compound (hereinafter referred to as Compound D). ) 40.0 mg was obtained as an amorphous. Melting point 154-156 [deg.] C.
[Α] _D + 51.20 ° (C = 0.500, chloroform-methanol (1: 1)).

Elemental analysis C ₁₈ H ₃₃ O ₈ NS Calculated value C 51.05, H 7.85, N 3.31 Measured value C 51.22, H 7.91, N 3.28 (3) n-hexyl 5-acetamide-3,5-dideoxy-2-thio-D -Glycero-α-D-galacto-2-nonuropyranoside acid acid Compound D (25 mg) was dissolved in dioxane (2 ml), and 0.2N aqueous potassium hydroxide solution (1.5 ml) was added dropwise with stirring at 0 ° C. Then, the mixture was returned to room temperature and stirred for 4 hours. After confirming the completion of the reaction by TLC, Amberlite I washed with water beforehand
R-120 (cation exchange resin) pH adjusted to around 6,
The resin was removed by cotton filtration and washed with water. The filtrate and washings were combined and freeze-dried as it was to quantitatively obtain the title compound as an amorphous substance. Melting point 139-141 [deg.] C. [Α] _D +
33.58 ° (C = 0.262, dioxane-water (1: 1)).

Elemental analysis C ₁₇ H ₃₁ O ₈ NS Calcd C 49.86, H 7.63, N 3.42 Found C 49.58, H 7.82, N 3.33 Example 3 (1) methyl (n- dodecyl-5-acetamido -4,7,8 , 9
-Tetra-0-acetyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonuropyranosonate Compound B (180 mg) and 1-bromododecane (127.2 mg) were used in Example 2 ( The reaction was performed in the same manner as in 1) to obtain 200 mg of the title compound (hereinafter, compound E) as an amorphous substance. Melting point 48-50 [deg.] C. [Α] _D + 21.35 ° (C = 0.693, chloroform).

Elemental analysis C ₃₂ H ₅₃ NO ₁₂ S Calculated value C 56.87, H 7.90, N 2.07 Measured value C 56.72, H 8.15, N 2.06 (2) Methyl (n-dodecyl-5-acetamido-3,5-dideoxy-2-) Thio-D-glycero-α-D-galacto-2-nonulopyranoside) onate Compound E (120 mg) was reacted in the same manner as in Example 2 (2) to quantitatively obtain the title compound (hereinafter, compound F) as amorphous. Melting point 88-90 [deg.] C.

[Α] _D + 41.63 ° (C = 0.932, chloroform-methanol (1: 1)).

Elemental analysis C ₂₄ H ₄₅ O ₈ NS Calculated value C 56.78, H 8.93, N 2.76 Measured value C 56.60, H 9.25, N 2.70 (3) 5-acetamido-3,5-dideoxy-2-S-dodecyl-2- Thio-D-glycero-α-D-galacto-2
-Nonuropyranosonic Acid Compound F (50 mg) was reacted in the same manner as in Example 2 (3) to quantitatively obtain the title compound as an amorphous substance. Melting point 149
~ 151 ° C. [Α] _D + 18.87 ° (C = 0.498, dioxane).

Elemental analysis C ₂₃ H ₄₃ O ₈ NS Calculated value C 55.96, H 8.78, N 2.84 Measured value C 55.71, H 8.93, N 2.78 Example 4 (1) Methyl (n-octadecyl-5-acetamide-4,
7,8,9-Tetra-0-acetyl-3,5-dideoxy-2-
Thio-D-glycero-α-D-galacto-2-nonuropyranoside) onate Compound B 144 mg and 1-bromo-octadecane 135.0 m
g in the same manner as in Example 2 (1) to give the title compound (hereinafter,
Compound G) 143.4 mg was obtained as a syrup. [Α] _D +2
1.3 ° (C = 0.48, chloroform).

Elemental analysis Calculated value as C ₃₈ H ₆₅ O ₁₂ NS C 60.06, H 8.62, N 1.84 Measured value C 60.23, H 8.90, N 1.85 (2) Methyl (n-octadecyl-5-acetamide-3,5
-Dideoxy-2-thio-D-glycero-α-D-galacto-2-nonuropyranoside) onate Compound 143 mg was reacted in the same manner as in Example 2 (2) to quantitatively give the title compound (hereinafter, compound H) as an amorphous substance. Got to. Melting point 104-106 [deg.] C. [Α] _D + 41.9 ° (C = 0.39, chloroform-methanol (1: 1)).

Elemental analysis C ₃₀ H ₅₇ O ₈ NS Calculated value C 60.88, H 9.71, N 2.37 Measured value C 60.56, H 9.85, N 2.26 (3) 5-acetamido-3,5-dideoxy-2-S-octadecyl-2- Thio-D-glycero-α-D-galacto-2-nonulopyranosonic acid Compound 50 mg was reacted in the same manner as in Example 2 (3) to quantitatively obtain the title compound as an amorphous substance. Melting point 124
~ 126 ° C. [Α] _D + 12.70 ° (C = 0.181, dioxane-water (1: 1)).

Elemental analysis C ₂₉ H ₅₅ O ₈ NS Calculated value C 60.28, H 9.59, N 2.42 Measured value C 60.11, H 9.78, N 2.42 Example 5 (1) Methyl 2,3,4-tri-0-acetyl-6- S-
(Methyl 5-acetamide-4,7,8,9-tetra-0-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonuropyranosylonate) -6-thio-2
-D-Glucopyranoside Compound B (192 mg) was dissolved in dry dimethylformamide (2 ml), and the mixture was stirred at 0 ° C. 208.5 mg of methyl 2,3,4-tri-0-acetyl-6-bromo-6-deoxy-α-D-glucopyranoside was dissolved in 2 ml of dry dimethylformamide in advance and added dropwise to the reaction solution. Then, the mixture was stirred at 60 ° C. for 1 day under nitrogen substitution. After confirming the completion of the reaction by TLC, the solvent was distilled off under reduced pressure at 60 ° C. and azeotroped with toluene several times. After extraction with chloroform, the chloroform layer was washed with water and dehydrated with anhydrous sodium sulfate. Sodium sulfate was removed by cotton filtration and washed with chloroform.
The filtrate and washings were combined and concentrated under reduced pressure. The obtained syrup was purified by column chromatography (eluting solvent: chloroform-methanol (150: 1)) to obtain 266.4 mg of the title compound (hereinafter, compound J) as an amorphous substance. Melting point 104-106 [deg.] C. [Α] _D + 77.2 ° (C = 5.83, chloroform).

Elemental analysis C ₃₃ H ₄₇ O ₂₀ NS Calculated value C 50.71, H 2.45, N 1.79 Measured value C 50.50, H 2.63, N 1.75 (2) Methyl-6-S- (methyl 5-acetamide-3,5
-Dideoxy-D-glycero-α-D-galacto-2-
Nonuropyranosylonate) -6-thio-α-D-glucopyranoside Compound J 235 mg was dissolved in anhydrous methanol 5 ml-10
Stirred at ° C. A catalytic amount of sodium methoxide was added, and the mixture was returned to room temperature and stirred for 8 hours. After confirming the completion of the reaction by TLC, the mixture was neutralized with Amberlite IR-120 (cation exchange resin), and the resin was removed by cotton filtration and washed with methanol. The filtrate and washings were combined and concentrated under reduced pressure to quantitatively obtain the title compound (hereinafter, compound K) as an amorphous substance. Melting point 127-
129 ° C. [Α] _D + 83.38 ° (C = 1.342, chloroform-methanol (1: 1)).

Elemental analysis C ₁₉ H ₃₃ O ₁₃ NS Calculated value C 44.27, H 6.45, N 2.72 Measured value C 44.03, H 6.59, N 2.70 (3) Methyl 6-S- (5-acetamido-3,5-dideoxy-2- Thio-D-glycero-α-D-galacto-2
-Nonuropyranosonic acid) -α-D-glucopyranoside Compound K (150 mg) was dissolved in dioxane (3 ml), and 0.2 N aqueous potassium hydroxide solution (2 ml) was added dropwise with stirring at 0 ° C. It returned to room temperature and stirred for 3.5 hours. Amberlite IR washed with water after confirming completion of reaction by TLC
The pH was adjusted to around 6 with -120 (cation exchange resin).
The resin was removed by cotton filtration and washed with water. The filtrate and washings were combined and freeze-dried as it was to quantitatively obtain the title compound as an amorphous substance. Melting point 184-186 [deg.] C. [Α] _D
+ 80.31 ° (C = 0.767, dioxane-water (1: 1)).

Elemental analysis C ₁₈ H ₃₁ O ₁₃ NS Calculated value C 43.11, H 6.23, N 2.79 Measured value C 42.85, H 6.51, N 2.63 Example 6 (3) Methyl 2,3,4-tri-0-acetyl-6- S-
(Methyl 5-acetamide-4,7,8,9-tetra-0-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonuropyranosylonate) -6-thio-
α-D-Galactopyranoside Compound B (110 mg) and methyl 2,3,4 tri-0-acetyl-6-bromo-6-deoxy-α-D-galactopyranoside (121.2 mg) were used in Example 5 (1 11) mg of the title compound (hereinafter referred to as compound L) as an amorphous substance. Melting point 100-102 [deg.] C. [Α] _D +6
8.01 ° (C = 1.016, chloroform).

Elemental analysis C ₃₃ H ₄₇ O ₂₀ NS Calculated value C 50.71, H 2.45, N 1.79 Measured value C 50.52, H 2.62, N 1.71 (2) Methyl 6-S- (methyl 5-acetamide-3,5
-Dideoxy-D-glycero-α-D-galacto-2-
Nonuropyranosylonate) -6-thio-α-D-galactopyranoside Compound L (100 mg) was reacted in the same manner as in Example 5 (2) to quantitatively obtain the title compound (hereinafter, Compound M) as an amorphous substance. . Melting point 139-141 [deg.] C. [Α] _D + 76.44 ° (C = 0.692, chloroform-methanol (1:
1)).

Elemental analysis C ₁₉ H ₃₃ O ₁₃ N ₉ Calculated value C 44.27, H 6.45, N 2.72 Measured value C 44.25, H 6.69, N 2.63 (3) Methyl 6-S- (5-acetamido-3,5-dideoxy-D -Glycero-α-D-galacto-2-nonulopyranosonic acid) -6-thio-α-D-galactopyranoside Compound M (35 mg) was reacted in the same manner as in Example 5 (3) to give the title compound quantitatively. It was obtained as an amorphous material. Melting point 174
~ 176 ° C. [Α] _D + 74.66 ° (C = 0.375, dioxane-water (1: 1)).

Elemental analysis C ₁₈ H ₃₁ O ₁₃ NS Calculated value C 43.11, H 6.23, N 2.79 Measured value C 43.06, H 6.33, N 2.75 Example 7 (1) Allyl 2,3,4-tri-0-acetyl-6- Bromo-6-deoxy-β-D-glucopyranoside 920 mg of allyl β-D-glucopyranoside was dissolved in 10 ml of dry pyridine and stirred at 0 ° C. Carbon tetrabromide (1.67 g) and triphenylphosphine (1.65 g) were added to this solution, followed by stirring at room temperature. After about 2 hours, 200 mg of carbon tetrabromide and 200 mg of triphenylphosphine were added, and the mixture was further stirred for about 2 hours at room temperature. After confirming the completion of the reaction by TLC, methanol was added and the reaction solution was concentrated under reduced pressure and azeotropically distilled several times with toluene. The obtained syrup was purified by column chromatography (elution solvent: chloroform-methanol (50: 1)) to give allyl 6-bromo-6.
430 mg of -deoxy-β-D-glucopyranoside were obtained as a syrup. 350 mg of this syrup was dissolved in 3 ml of dry pyridine, and 1.5 ml of acetic anhydride was added with stirring at 0 ° C. After returning to room temperature and stirring for about 2 hours, the completion of the reaction was confirmed by TLC, and methanol was added. The reaction solution was distilled off under reduced pressure,
It was azeotropically distilled several times with toluene and extracted with chloroform. The chloroform layer was washed with 2N hydrochloric acid, an aqueous solution of sodium carbonate and water in this order, and dehydrated with anhydrous sodium sulfate. Sodium sulfate was removed by cotton filtration and washed with chloroform.
The filtrate and washings were combined and concentrated under reduced pressure to quantitatively obtain the title compound (hereinafter, compound N) as crystals. Melting point 109-111
° C. [Α] _D −7.13 ° (C = 1.037, chloroform).

Elemental analysis C ₁₅ H ₂₁ O ₈ Br Calculated value C 44.02, H 5.17 Measured value C 43.96, H 5.20 (2) Allyl 2,3,4-tri-0-acetyl-6-S-
(Methyl 5-acetamide-4,7,8,9-tetra-0-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonuropyranosylonate) -6-thio-
β-D-Glucopyranoside Compound B (156.1 mg) and compound N (180 mg) were reacted in the same manner as in Example 5 (1) to give 173.1 mg of the title compound (hereinafter, compound O) as an amorphous substance. Melting point 89-9
1 ° C. [Α] _D + 25.17 ° (C = 0.564, chloroform).

Elemental analysis C ₃₅ H ₄₉ O ₂₀ NS Calculated value C 50.30, H 5.91, N 1.68 Measured value C 50.19, H 5.98, N 1.67 (3) Allyl 6-S- (methyl 5-acetamide-3,5
-Dideoxy-D-glycero-α-D-galacto-2-
Nonuropyranosylonate) -6-thio-β-D-glucopyranoside Compound O 127 mg was reacted in the same manner as in Example 5 (2) to obtain 69.1 mg of the title compound (hereinafter, compound P) as an amorphous substance. Melting point 119-121 [deg.] C. [Α] _D + 25.91 ° (C = 0.355, methanol).

Elemental analysis C ₂₁ H ₃₅ O ₁₃ NS Calculated value C 46.57, H 6.51, N 2.59 Measured value C 46.38, H 6.55, N 2.51 (4) Allyl 6-S- (5-acetamido-3,5-dideoxy-D- Glycero-α-D-galacto-2-nonulopyranosonic acid) -6-thio-β-D-glucopyranoside Compound P 35 mg was reacted in the same manner as in Example 5 (3) to quantitatively obtain the title compound as an amorphous substance. It was Melting point 161
~ 163 ° C. [Α] _D + 29.94 ° (C = 0.354, water).

Elemental analysis C ₂₀ H ₃₃ O ₁₃ NS Calculated value C 45.54, H 6.31, N 2.66 Measured value C 45.51, H 6.43, N 2.69 Example 8 (1) Allyl 2-acetamido-3,4-di-0-acetyl- 6-Bromo-2,6-dideoxy-β-D-glucopyranoside Allyl 2-acetamido-β-D-glucopyranoside 1.
1 g, carbon tetrabromide 1.58 g and triphenylphosphine 1.5
Allyl 2 was reacted in the same manner as in Example 7 (1) using 7 g.
-Acetamide-6-bromo-2,6-dideoxy-β-D
590 mg of glucopyranoside was obtained as a syrup. 580 mg of this and 1.5 ml of acetic anhydride were reacted in the same manner as in Example 7 (1) to quantitatively obtain the title compound (hereinafter, compound Q) as crystals. Melting point 174-176 [deg.] C. [Α] _D
−4.50 ° (C = 2.22, chloroform).

Elemental analysis C ₁₅ H ₂₂ O ₇ NBr Calculated value C 44.13, H 5.43, N 3.43 Measured value C 44.15, H 5.40, N 3.39 (2) Allyl 2-acetamide-3,4-di-0-acetyl-2-deoxy -6-S- (methyl 5-acetamide-
4789-Tetra-0-acetyl-3,5-dideoxy-
D-Glucero-α-D-galacto-2-nonuropyranosylonate) -6-thio-β-D-glucopyranoside Compound B176.3 mg and compound Q202.1 mg were reacted in the same manner as in Example 5 (1). Title compound (hereinafter, compound R) 240
mg was obtained as an amorphous. Melting point 123-125 [deg.] C.
[Α] _D + 27.91 ° (C = 0.695, chloroform).

Elemental analysis C ₃₅ H ₅₀ O ₁₉ N ₂ S Calculated value C 50.35, H 6.04, N 3.36 Measured value C 50.11, H 6.31, N 3.27 (3) Allyl 2-acetamido-2-deoxy-6-S
-(Methyl 5-acetamide-3,5-dideoxy-D-
Glucero-α-D-galacto-2-nonuropyranosylonate) -6-thio-β-D-glucopyranoside Compound R210 mg was reacted in the same manner as in Example 5 (2) to give the title compound (hereinafter, Compound S). It was obtained quantitatively as an amorphous. Melting point 210-212 [deg.] C. [Α] _D + 22.08 ° (C = 1.354, methanol).

Elemental analysis C ₂₁ H ₃₆ O ₁₂ N ₂ S Calculated value C 46.66, H 6.71, N 5.18 Measured value C 46.63, H 6.58, N 5.06 (4) Allyl 2-acetamido-2-deoxy-6-S
-(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonuropyranosonic acid) -6-thio-β-D-glucopyranoside Compound S (100 mg) was used as Example 5 (3). The same reaction was performed to obtain 93 mg of the title compound as an amorphous substance. Melting point 208
~ 210 ° C. [Α] _D +36.02 (C = 0.93, water).

Elemental analysis C ₂₀ H ₃₄ O ₁₂ N ₂ S Calculated value C 45.62, H 6.51, N 5.32 Measured value C 45.46, H 6.78, N 5.20

Claims (1)

[Claims] 1. A general formula [In the formula, R ₁ and R ₂ represent an acyl group or hydrogen, R ₃ represents an acyl group, R ₄ represents hydrogen or a lower alkyl group, and R ₅ represents (Wherein, R ₆ is hydrogen, an allyl group or a lower alkyl group, R ₇
Means an acylamino group or a hydroxyl group) and an S-neuraminic acid derivative represented by