Synthetic Route of 10343-06-3, An article , which mentions 10343-06-3, molecular formula is C14H20O10. The compound – 2,3,4,6-Tetra-o-acetyl-D-glucopyranose played an important role in people’s production and life.
The 2,3,4,6-tetra-O-benzyl-1-O-(N-benzyloxycarbonyltripeptidyl)-D-glucopyranoses 1, 8, and 13 were synthesised from 2,3,4,6-tetra-O-benzyl-alpha-D-glucopyranose and the active esters of the appropriate N-protected tripeptides (Gly-Gly-Gly-, L-Phe-Gly-Gly-, and Gly-Gly-L-Phe-) in the presence of imidazole; the anomeric mixtures were resolved and the alpha and beta anomers characterised.The beta anomer of 13, containing the L and D enantiomers (ratio ca. 3:1) of Gly-Gly-Phe- as the aglycon, could be resolved by column chromatography into the pure isomeric forms.Catalytic hydrogenolysis of the beta anomers, in the presence and absence of a strong acid, yielded the free 1-esters 2beta, 9beta, and 14beta, which were characterised as the mono-oxalate or trifluoroacetate salts and as free bases.Similarly, the alpha anomers afforded 2alpha, 9alpha, and 14alpha, whereas omission of the strong acid led to accompanying 1 –> 2 acyl migration, to give the 2-O-acyl derivatives.All of the compounds prepared were converted into the N-acetyl and/or peracetylated derivatives.The 1-esters 2beta and 9beta, both in the charged and uncharged form, and the trifluoroacetate salt of 14beta, are susceptible to cleavage by beta-D-glucosidase; the enzyme had no effect on the uncharged form of 14beta.This difference between 14beta and its salt is discussed in conformational terms.
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Reference：
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics