cas 137915-37-8, 6-O-(TRIISOPROPYLSILYL)-D-GLUCAL | Articles data ｜lookchem

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137915-37-8

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One-pot conversion of glycals to cis-1,2-isopropylidene-α-glycosides
Described is a general method for the conversion of glycals to the corresponding 1,2-cis-isopropylidene-α-glycosides. Epoxidation of glycals with dimethyldioxirane followed by ZnCl2-catalyzed addition of acetone converted a variety of protected glycals into 1,2-cis-isopropylidene-α-glycosides in good yield. The reaction is compatible with a range of protecting groups, including esters, benzyl ethers, and silyl ethers, as well as free hydroxyl groups. This method has been applied to develop a synthesis of protected glucuronic acid 1, a key intermediate in the synthesis of glycosaminoglycans. Compound 1 was produced in seven steps and 32% overall yield.
Lohman, Gregory J. S.,Seeberger, Peter H.
p. 7541 - 7543
(2007/10/03)

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Chemical Properties

Boiling Point: 361.886°C at 760 mmHg
Flash Point:113 °C
Density: 0.726 g/mL at 25 °C(lit.)
Vapor Pressure: 0mmHg at 25°C
Refractive Index: n20/D 1.489(lit.)
PSA: 58.92000
LogP: 2.81280

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