221371-27-3

Basic information

• Product Name: (1R,2S,3S,4R)-3,4-di-O-benzyl-5-(benzyloxymethyl)-1,2-O,O-sulfonylcyclohex-5-ene-1,2,3,4-tetraol
• Synonyms: (1R,2S,3S,4R)-3,4-di-O-benzyl-5-(benzyloxymethyl)-1,2-O,O-sulfonylcyclohex-5-ene-1,2,3,4-tetraol
• CAS NO: 221371-27-3
• Molecular Weight: 492.593
• Mol File: 221371-27-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (1R,2S,3S,4R)-3,4-di-O-benzyl-5-(benzyloxymethyl)-1,2-O,O-sulfonylcyclohex-5-ene-1,2,3,4-tetraol(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2S,3S,4R)-3,4-di-O-benzyl-5-(benzyloxymethyl)-1,2-O,O-sulfonylcyclohex-5-ene-1,2,3,4-tetraol(221371-27-3)
• EPA Substance Registry System: (1R,2S,3S,4R)-3,4-di-O-benzyl-5-(benzyloxymethyl)-1,2-O,O-sulfonylcyclohex-5-ene-1,2,3,4-tetraol(221371-27-3)

Safety Data

• Hazardous Substances Data: 221371-27-3(Hazardous Substances Data)

Upstream product

• 221371-25-1 (1R,2R,3R,4R)-3,4-di-O-benzyl-5-(benzyloxymethyl)cyclohex-5-ene-1,2,3,4-tetraol 
• 100-39-0 benzyl bromide 
• 221371-19-3 (1R,2R,3R,4S,5S)-3,4-di-O-benzyl-5-(benzyloxymethyl)-1,2-O-cyclohexylidene-1,2,3,4,5-cyclohexanepentol 
• 221371-23-9 (1R,2R,3S,4R)-3,4-di-O-benzyl-5-(benzyloxymethyl)-1,2-O-cyclohexylidenecyclohex-5-ene-1,2,3,4-tetraol 
• 183268-55-5 (1R,2R,3S,4S,5S)-3-O-benzyl-5-((benzyloxy)methyl)-1,2-O-cyclohexylidenecyclohexane-1,2,3,4,5-pentol 

Downstream Products

• 221371-29-5 (1S,2R,3R,4R)-1-azido-3,4-di-O-benzyl-5-(benzyloxymethyl)cyclohex-5-ene-2,3,4-triol 
• 38231-86-6 valienamine 
• 221371-39-7 (1S,2S,3R,4R)-1-amino-3,4-di-O-benzyl-5-(benzyloxymethyl)cyclohex-5-ene-2,3,4-triol 
• 221371-17-1 2-epi-valienamine 
• 221371-31-9 (1S,2R,3R,4R)-1-amino-3,4-di-O-benzyl-5-(benzyloxymethyl)cyclohex-5-ene-2,3,4-triol 
• 221371-38-6 (1S,2S,3R,4R)-1-azido-3,4-di-O-benzyl-5-(benzyloxymethyl)cyclohex-5-ene-2,3,4-triol 
• 221371-37-5 (1S,2R,3S,4R)-1-azido-3,4-di-O-benzyl-5-(benzyloxymethyl)-2-O-methanesulfonylcyclohex-5-ene-2,3,4-triol 
• 221371-30-8 (1S,2R,3R,4R)-2-O-acetyl-1-azido-3,4-di-O-benzyl-5-(benzyloxymethyl)cyclohex-5-ene-2,3,4-triol 
• 221371-97-7 (1S,2S,3S,4R)-2-O-acetyl-1-azido-3,4-di-O-benzyl-5-(benzyloxymethyl)cyclohex-5-ene-2,3,4-triol 
• 221371-34-2 (1S,2R,3S,4R)-1-azido-3,4-di-O-benzyl-5-(benzyloxymethyl)-2-O-trifluoromethanesulfonylcyclohex-5-ene-2,3,4-triol 

Relevant articles and documents

Enantiospecific syntheses of valienamine and 2-epi-valienamine

Cyclic sulfite 10, readily available from (-)-quinic acid (3) in 10 steps, was ring opened regio- and stereospecifically with azide anion to give (1S,2R,3R,4R)-1-azido-3,4-di-O-benzyl-5-(benzyloxymethyl)cyclohex-5-ene- 2,3,4-triol (11). Deprotection of 11 afforded, for the first time, 2- epivalienamine (2), which was isolated as penta-N,O-acetyl-2-epi-valienamine (14). The configuration of the free hydroxy group in 11 was inverted by a two-step sequence to give the blocked valienamine 19 that was deprotected to give valienamine (1), isolated as penta-N,O-acetylvalienamine (21). This approach furnished (+)-valienamine (1) in 16 steps (7% overall yield) and recorded the first synthesis of 2-epi-valienamine (2) in 13 steps (11% overall yield).