Extended knowledge of 2,3,4,6-Tetra-o-acetyl-D-glucopyranose

Interested yet? Keep reading other articles of 10343-06-3!, Quality Control of: 2,3,4,6-Tetra-o-acetyl-D-glucopyranose

Children learn through play, and they learn more than adults might expect. Science experiments are a great way to spark their curiosity, get their minds active, and encourage them to do something that doesn¡¯t involve a screen. 10343-06-3, C14H20O10. A document type is Article, introducing its new discovery., Quality Control of: 2,3,4,6-Tetra-o-acetyl-D-glucopyranose

SYNTHESIS AND REACTIONS OF D-GLUCOPYRANOSYL ESTERS OF PHENYLALANINE AND TYROSINE: A STUDY OF THE DIAZOMETHANE-CATALYSED 1->2 ACYL MIGRATION OF THE N-ACYLATED alpha-D ANOMERS

The fully benzylated alpha- and beta-D-glucopyranosyl esters of N-benzyloxycarbonyl- and N-tert-butoxycarbonyl-L-phenylalanine (1 and 5, respectively) have been converted into 1-O-(L-phenylalanyl)-alpha- and -beta-D-glucopyranose, which were isolated as trifluoroacetate salts (2alpha and 2beta).On dissolution in water, 1-O--alpha-D-glucopyranose (6a) gave the anomerised C-2 isomer 8 and hydrolysis products of 6alpha.Treatment of 6alpha with N,N-dimethylformamide-ethereal diazomethane gave the 2-O-acyl derivative 8alpha (>80percent). 1-O-(L-Tyrosyl)-alpha-(12alpha) and -beta-D-glucopyranose (12beta), isolated as the trifluoroacetate salts, were prepared from 2,3,4,6-tetra-O-benzyl-1-O--alpha- and -beta-D-glucopyranose (10) and characterised as the N-acetyl- (13) and tetra-acetate derivatives (14).Treatment of 13alpha with diazomethane caused extensive hydrolysis, but some rearrangement into the 2-O-acyl derivative 15alpha, which was characterised as crystalline 1,3,4,6-tetra-O-acetyl-2-O-(N-acetyl-O-acetyl-L-tyrosyl)-alpha-D-glucopyranose (16alpha).The foregoing 1->2 acyl migrations and hydrolyses are competitive reactions, the relative rates of which are strongly affected by reaction temperature and the nature of the acyl group.

Interested yet? Keep reading other articles of 10343-06-3!, Quality Control of: 2,3,4,6-Tetra-o-acetyl-D-glucopyranose

Reference£º
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics