Preparation of 1-.alpha.- and 1-.beta.-glucose esters by stereos

Details Preparation of 1-.alpha.- and 1-.beta.-glucose esters by stereos Preparation of 1-.alpha.- and 1-.beta.-glucose esters by stereos

1977-02-15

1978-08-15

Brown, Johnnie R.

Organic compounds -- part of the class 532-570 series

Organic compounds

Carbohydrates or derivatives

536 4, 536115, 536121, C07H 1302

Patent

active

041074254

ABSTRACT:
Anomerically pure 1-.alpha.- and 1-.beta.-esters of 2,3,4,6-Tetra-O-benzyl-D-glucopyranose have been prepared in high yield by controlling the stereochemistry of 1-O-acylation of appropriately protected D-glucose. 2,3,4,6-tetra-O-benzyl-D-glucopyranose is metalated with n-butyllithium in either tetrahydrofuran or anhydrous benzene and the metalated product acylated with an appropriate alkyl, alkenyl, or aryl acid chloride. Hydrogenation of the acyl glucopyranose, when derived from a saturated acid chloride, yields the appropriate 1-.alpha.- or 1-.beta.-D-glucose ester. Reaction in tetrahydrofuran produces the .alpha.-anomer while reaction in anhydrous benzene produces the .beta.-anomer.

REFERENCES:
patent: 1994608 (1935-03-01), Hagedorn
patent: 3756966 (1973-09-01), Lamberti
patent: 3849341 (1974-11-01), Lamberti
patent: 3981860 (1976-09-01), Szkrybalo

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