93164-50-2

Basic information

• Product Name: 2,4-O-benzylidene-5,6-O-isopropylidene-D-glucitol
• Synonyms: 2,4-O-benzylidene-5,6-O-isopropylidene-D-glucitol
• CAS NO: 93164-50-2
• Molecular Weight: 310.347
• Mol File: 93164-50-2.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 2,4-O-benzylidene-5,6-O-isopropylidene-D-glucitol(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-O-benzylidene-5,6-O-isopropylidene-D-glucitol(93164-50-2)
• EPA Substance Registry System: 2,4-O-benzylidene-5,6-O-isopropylidene-D-glucitol(93164-50-2)

Safety Data

• Hazardous Substances Data: 93164-50-2(Hazardous Substances Data)

Upstream product

• 61340-09-8 (2S,4R,5R,6S)-4-<(1R)-1,2-dihydroxyethyl>-5-hydroxy-6-hydroxymethyl-2-phenyl-1,3-dioxane 
• 50-70-4 D-sorbitol 
• 100-52-7 benzaldehyde 
• 77340-95-5 monofurfurylidene-2,4-sorbitol 
• 77-76-9 2,2-dimethoxy-propane 

Downstream Products

• 887258-66-4 2,4-O-benzylidene-5,6-O-isopropylidene-D-glucitol-1,3-cyclic sulfate 
• 887258-77-7 2,3,5-tri-O-p-methoxybenzyl-1,4-dideoxy-1,4-[[(2R,3S,4R,5R)-2,4-benzylidenedioxy-5,6-isopropylidenedioxy-3-(sulfooxy)hexyl]iminoniumlidene]-D-arabinitol inner salt 
• 887258-78-8 2,3,5-tri-O-p-methoxybenzyl-1,4-dideoxy-1,4-[[(2R,3S,4R,5R)-2,4-benzylidenedioxy-5,6-isopropylidenedioxy-3-(sulfooxy)hexyl]iminoniumlidene]-L-arabinitol inner salt 
• 876062-92-9 1,3-bis-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2,4-O-benzylidene-5,6-O-isopropylidene-D-glucitol 
• 876062-90-7 1-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2,4-O-benzylidene-5,6-O-isopropylidene-D-glucitol 
• 794591-52-9 1-O-benzoyl-2,4-O-benzylidene-5,6-O-isopropylidene-3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-D-glucitol 
• 794591-54-1 2,4-O-benzylidene-5,6-O-isopropylidene-3-O-(β-D-glucopyranosyl)-D-glucitol 
• 794591-49-4 1-O-benzoyl-2,4-O-benzylidene-5,6-O-isopropylidene-D-glucitol 

Relevant articles and documents

Two approaches to the synthesis of 3-β-D-glucopyranosyl-D-glucitol

Glycosidation of 1,2:5,6-di-O-isopropylidene-d-glucose with tetra-O-acetyl-glucosyl bromide in 1:1 benzene-MeNO2 afforded approximately equal amounts of the 3-O-β-d-glycoside and the rearranged 6-O-β-d-glycoside, while in MeCN only the latter was formed. When tetra-O-acetyl-β-thiophenylglucoside was used as donor in CH 2Cl2 in the presence of NIS/TfOH as activator, the 6-O-β-d-glycoside and a 3-O-orthoester were formed in a 1:2 ratio at -20°C, while at 20°C only the former could be isolated. Glycosidation of 1-O-benzoyl-2,4-O-benzylidene-5,6-O-isopropylidene-d-glucitol with tetra-O-acetyl-glucosyl bromide in MeCN in the presence of Hg(CN)2 afforded the corresponding 3-O-α- and 3-O-β-glycopyranoside in a 1:4 ratio in MeCN and 1:5 in 1:1 benzene-MeNO2, respectively. When Hg(CN)2/HgBr2 was used as promoter, the corresponding orthoester was also formed. When tetra-O-acetyl-β-thiophenylglucoside was used as donor, the 3-O-β-anomer and the orthoester were obtained predominantly in a 3:2 ratio together with traces of the 3-O-α-glycoside. Both β-glycosides could be smoothly converted into 3-β-d- glucopyranosyl-d-glucitol.