CN1406945A - Preparation of 1,2,5,6-diisopropylidene galactofructofuranose - Google Patents
Preparation of 1,2,5,6-diisopropylidene galactofructofuranose Download PDFInfo
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- CN1406945A CN1406945A CN 01131487 CN01131487A CN1406945A CN 1406945 A CN1406945 A CN 1406945A CN 01131487 CN01131487 CN 01131487 CN 01131487 A CN01131487 A CN 01131487A CN 1406945 A CN1406945 A CN 1406945A
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- acetone
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- dry hydrogen
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Abstract
A process for preparing 1,2;5,6-diisopropylidene galactofuranose features that use of a novel catalyst, dry hydrogen resin, that is, under the existance of dry hydrogen, the D-galactose dissolved in dried DMF and acetone is refluxed for 7-12 hr. Its advantages are easily available catalyst and high reaction transform rate.
Description
The present invention relates to a kind of synthetic 1,2; 5, the novel method of 6-two-O-isopropylidene-α-D-gala furanose, key of the present invention have been to use a kind of new catalyzer-dry hydrogen resin.
1,2; 5,6-two-O-isopropylidene-α-D-gala furanose is the precursor of synthetic multiple natural product.But up to the present the synthetic method of this compound is very limited ([1], [2], [3], [4]), subject matter is that the final product of these known synthetic method reactions is the mixture of gala furanose and gala pyranose, both have only 2: 1 the most at high proportion, and this causes major product to be difficult for separated and purifies.
The purpose of this invention is to provide a kind of synthetic new method of this gala furanose, this method has overcome the existing methods problem to a great extent.Make the ratio of gala furanose and gala pyranose bring up to 2.5: 1-3: 1, product is the separate easily purifying more.
In achieving the above object, the invention provides a kind of production 1,2; 5, the novel method of 6-two-O-isopropylidene-α-D-gala furanose, this method productive rate height is easy to make with extra care.
Preparation method's of the present invention characteristics are:
Used a kind of new catalyzer-dry hydrogen resin.Reflux with the catalyzer dry hydrogen and react being dissolved in D-semi-lactosi in DMF and the acetone.
Described catalyzer is the dry hydrogen resin, and this resin is Hydrogen, dry state, spherical large hole strong acid styrene system cation exchange resin.
Described acetone and DMF must be dry, and acetone must be excessive greatly, and the D-semi-lactosi must be dissolved among the DMF in advance.Reaction must under agitation reflux 7-12 hour.
Described post reaction mixture extracts 2-3 time with ethyl acetate and water after handling with underpressure distillation after filtration, and the product after the extraction can come partition method refining with crystallization process or column chromatography.
Further specify the present invention with example below
The catalyzer dry hydrogen is the board NKC-9 of a Nankai dry hydrogen catalytic resin, and this resin is Hydrogen, dry state, spherical large hole strong acid styrene system cation exchange resin.
React the day before yesterday with DMF hydrolith drying, acetone salt of wormwood drying.Filter 200 milliliters of DMF during reaction, add 10 gram D-gala furanoses, on heating jacket, heat, and on magnetic stirrer, stir, make the semi-lactosi dissolving.Filter 600 milliliters in acetone, add 12 gram dry hydrogens.The dissolved semi-lactosi is added in the acetone while hot.Under heating jacket heating and magnetic agitation, acetone is refluxed reaction mixture and react backflow 7-12 hour.
The mixture cooling back of reacting is filtered on funnel, then filtrate is concentrated, liquid ethyl acetate and water (volume ratio 1: 1) after concentrating, at every turn with 10 milliliters of extractions 2-3 time, get organic phase, organic phase is concentrated as far as possible, spissated raffinate is placed and was promptly had the crystal generation in 1-3 days.Again this crystal is carried out one time recrystallization, crystallization method be with the first time crystallisate be dissolved in the ethyl acetate of heat, drip sherwood oil then, to white opacity occurring, be placed in the refrigerator and just had recrystallization in 1-4 hour and occur.Just can obtain 1,2 through recrystallization operation back; 5, the purified white crystal of 6-two-O-isopropylidene-α-D-gala furanose.Also can purify by column chromatography in addition, used eluent proportioning is a sherwood oil: ethyl acetate=3: 1-4: 1.
Prepared 1,2; 5, the productive rate of 6-two-O-isopropylidene-α-D-gala furanose is 35%.
1HNMR(CDCl
3，400MHZ)：δ5.88(d，1H?J
1，2＝3.94，H-1)，4.55(dd，1H，J
1，2＝3.94，J
2，3＝1.28，H-2)，4.38-4.33(dd，1H，J
5，6＝13.3，J
5，6＝6.7，H-5)，4.12-4.05(m，2H，H-3，6)，3.88-3.83(m，2H，H-4，6)，1.55-1.35(3s，12H，4?CH
3)。Reaction formula is as follows
Annotate: a: acetone, DMF, dry hydrogen refluxes.
Reference [1] Svein, Morgenlie, Acta chem.Scand.1973,27,3609-3610.[2] H.Paulsen and H.Behre, Carbohydrate Res., 1966,2,80.[3] J.Lehmann, Carbohydrate Res., 1966,2,1.[4] A.P.Rauter et al.Tetrahedron.1995,23,6529-6540.
Claims (4)
1, a kind of synthetic 1,2; 5, the novel method of 6-two-O-isopropylidene-α-D-gala furanose.Be characterized in using a kind of new catalyzer-dry hydrogen resin.Reflux with the catalyzer dry hydrogen and react being dissolved in D-semi-lactosi in DMF and the acetone.
2, by the process of claim 1 wherein that described catalyzer is the dry hydrogen resin, this resin is Hydrogen, dry state, spherical large hole strong acid styrene system cation exchange resin.
3, by the method for claim 1, acetone and DMF must be dry, and acetone must be excessive greatly, and the D-semi-lactosi must be dissolved among the DMF in advance.Reaction must under agitation reflux 7-12 hour.
4. by the method for claim 1, post reaction mixture extracts 2-3 time with ethyl acetate and water after handling with underpressure distillation after filtration, and the product after the extraction can come partition method refining with crystallization process or column chromatography.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 01131487 CN1406945A (en) | 2001-09-12 | 2001-09-12 | Preparation of 1,2,5,6-diisopropylidene galactofructofuranose |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 01131487 CN1406945A (en) | 2001-09-12 | 2001-09-12 | Preparation of 1,2,5,6-diisopropylidene galactofructofuranose |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1406945A true CN1406945A (en) | 2003-04-02 |
Family
ID=4670620
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 01131487 Pending CN1406945A (en) | 2001-09-12 | 2001-09-12 | Preparation of 1,2,5,6-diisopropylidene galactofructofuranose |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1406945A (en) |
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2001
- 2001-09-12 CN CN 01131487 patent/CN1406945A/en active Pending
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