78136-21-7

Upstream product

• 18162-48-6 tert-butyldimethylsilyl chloride 
• 53929-48-9 (2R,3R,4S,5R)-1,3,4,5-tetrakis(benzyloxy)-6,6-bis(ethylthio)hexan-2-ol 
• 175470-19-6 tert-Butyl-dimethyl-((1R,2S,3S,4R)-2,3,4-tris-benzyloxy-1-benzyloxymethyl-5,5-bis-ethylsulfanyl-pentyloxy)-silane 
• 14233-48-8 (2S,3R,4R)-2,3,4,6-Tetrakis-benzyloxy-hexane-1,5-diol 
• 78136-18-2 tert-Butyl-dimethyl-((2S,3R,4S)-2,3,4-tris-benzyloxy-1-benzyloxymethyl-5-trityloxy-pentyloxy)-silane 
• 1045730-76-4 (3R,4R,5S)-1,3,4,5-Tetrakis-benzyloxy-6-trityloxy-hexan-2-ol 
• 78136-19-3 (2S,3R,4S)-2,3,4,6-Tetrakis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-hexan-1-ol 

Downstream Products

• 78184-89-1 2,3,4,6-tetra-O-benzyl-α-L-idopyranose 
• 4132-28-9 2,3,4,6-tetra-O-benzyl-β-L-idopyranose 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 

Relevant academic research and scientific papers

SYNTHESIS OF C-DISACCHARIDES AN UNUSUAL RING CLOSURE REACTION

Reaction of the 4-C-lithiomethyl intermediates, obtained from 4-deoxy-4-C-iodomethylglucopyranosides 5a,b, with open-chain glucose derivative 8 afforded 4-deoxy-4-C-heptitylglucopyranosides 9a,b.Mesylation of the newly generated hydroxy group and then desilylation gave 11a,b which were subjected to ring closure under basic conditions.Surprisingly, no C-bridged cellobiosides 12a,b (or, alternatively the corresponding maltosides) were obtained as major products; with loss of one benzyl alcohol residue the furanosides 13a,b were preferentially formed.Their generation and structural assignment is discussed.

SYNTHESIS OF 2,3,4,6-TETRA-O-BENZYL-L-IDOPYRANOSE

A synthesis of 2,3,4,6-tetra-O-benzyl-L-idopyranose (15) is described, based on L-sorbose as the starting material.By a succession of well known, high-yielding procedures, the ketose was converted into a 2:1 mixture of 1,3,4,5-tetra-O-benzyl-2-O-(tert-but