220931-01-1

Basic information

• Product Name: 3-O-(1,3-Diphenylprop-2-en-1-yl)-D-glucal
• Synonyms: 3-O-(1,3-Diphenylprop-2-en-1-yl)-D-glucal
• CAS NO: 220931-01-1
• Molecular Weight: 338.403
• Mol File: 220931-01-1.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 3-O-(1,3-Diphenylprop-2-en-1-yl)-D-glucal(CAS DataBase Reference)
• NIST Chemistry Reference: 3-O-(1,3-Diphenylprop-2-en-1-yl)-D-glucal(220931-01-1)
• EPA Substance Registry System: 3-O-(1,3-Diphenylprop-2-en-1-yl)-D-glucal(220931-01-1)

Safety Data

• Hazardous Substances Data: 220931-01-1(Hazardous Substances Data)

Upstream product

• 121441-07-4 (E)-1,3-diphenyl-3-chloroprop-1-ene 
• 13265-84-4 D-glucal 
• 220931-00-0 3-O-(1,3-Diphenylprop-2-en-1-yl)-6-O-t-butyldiphenylsilyl-D-glucal 

Downstream Products

• 220931-02-2 4,6-Di-O-benzoyl-3-O-(1,3-diphenylprop-2-en-1-yl)-D-glucal 
• 181506-86-5 Methyl 4,6-di-O-benzoyl-3-O-benzyl-2-deoxy-2-C-formyl-α-D-mannopyranoside 
• 220931-04-4 C₂₉H₂₇IO₈ 
• 220931-03-3 Methyl 4,6-di-O-benzoyl-2-deoxy-3-O-(1,3-diphenylprop-2-en-1-yl)-2-iodo-α-D-mannopyranoside 
• 181506-90-1 Methyl 4,6-di-O-benzoyl-3-O-benzyl-2-deoxy-2-C-(2-O-tert-butyldimethylsilyl-3,4,6-tri-O-benzyl-α-D-mannopyranosylmethyl)-α-D-mannopyranoside 
• 181506-88-7 Methyl 4,6-di-O-benzoyl-3-O-benzyl-2-deoxy-2-C-(2-O-tert-butyldimethylsilyl-3,4,6-tri-O-benzyl-α-D-mannopyranosylhydroxy-methyl)-α-D-mannopyranoside 
• 181506-89-8 Methyl 4,6-di-O-benzoyl-3-O-benzyl-2-deoxy-2-C-<2-O-tert-butyldimethylsilyl-3,4,6-tri-O-benzyl-α-D-mannopyranosylmethyl(xanthateimidazole)>-α-D-mannopyranoside 
• 188893-05-2 p-Methoxyphenylmethyl 4,6-di-O-benzoyl-3-O-benzyl-2-deoxy-2-C-formyl-α-D-mannopyranoside 
• 188893-20-1 p-Methoxyphenylmethyl 4,6-di-O-benzoyl-3-O-benzyl-2-deoxy-2-C-(2-O-tert-butyldimethylsilyl-3,4,6-tri-O-benzyl-α-D-mannopyranosylhydroxy-methyl)-α-D-mannopyranoside 
• 220931-25-9 p-Methoxyphenylmethyl 4,6-di-O-benzoyl-2-deoxy-3-O-(1,3-diphenylprop-2-en-1-yl)-2-iodo-α-D-mannopyranoside 
• 220931-22-6 C₄₄H₄₆O₈Si 
• 220931-21-5 C₅₂H₅₄O₉Si 

Relevant articles and documents

Samarium diiodide promoted C-glycosylation: An application to the stereospecific synthesis of α-1,2-C-mannobioside and its derivatives

The synthesis of the C-glycoside analogue of the disaccharide Man(α1 → 2)Man has been achieved in a highly stereoselective and efficient manner employing an approach which closely parallels O-glycoside synthesis. The key step included the samarium diiodide reduction of mannosyl pyridylsulfone 18 in the presence of the C2-formyl branched mannoside derivative 17a to furnish the C-disaccharide derivative 19a in high yield. An intramolecular formyl group transfer reaction by means of 5-exo radical cyclization and concomitant fragmentation yielded aldehyde 17a stereospecifically. We also present a potentially viable alternative for the deoxygenation of sterically encumbered secondary alcohols. Attempts to extend this procedure to the synthesis of the C-trisaccharide of Man(α1 → 2)Man(α1 → 2)Man were frustrated by the inability of the disaccharide, pyridylsulfone derivative 43, to undergo coupling with carbonyl substrates upon treatment with SmI2, possibly owing to the sterically bulky C2 substituent.