183505-14-8

Basic information

• Product Name: (1S,2S,3R,4S,5S)-1-azido-3-O-benzyl-5-((benzyloxy)methyl)cyclohexane-2,3,4,5-tetrol
• Synonyms: (1S,2S,3R,4S,5S)-1-azido-3-O-benzyl-5-((benzyloxy)methyl)cyclohexane-2,3,4,5-tetrol
• CAS NO: 183505-14-8
• Molecular Weight: 399.447
• Mol File: 183505-14-8.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (1S,2S,3R,4S,5S)-1-azido-3-O-benzyl-5-((benzyloxy)methyl)cyclohexane-2,3,4,5-tetrol(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2S,3R,4S,5S)-1-azido-3-O-benzyl-5-((benzyloxy)methyl)cyclohexane-2,3,4,5-tetrol(183505-14-8)
• EPA Substance Registry System: (1S,2S,3R,4S,5S)-1-azido-3-O-benzyl-5-((benzyloxy)methyl)cyclohexane-2,3,4,5-tetrol(183505-14-8)

Safety Data

• Hazardous Substances Data: 183505-14-8(Hazardous Substances Data)

Upstream product

• 171339-44-9 (1R,2S,3S,4S,5S)-4,5-di-O-acetyl-3-O-benzyl-5-((benzyloxy)methyl)-1,2-O,O-sulfonylcyclohexane-1,2,3,4,5-pentol 
• 171252-90-7 (1S,2R,3R,4S,5S)-1-azido-4,5-di-O-acetyl-3-O-benzyl-5-((benzyloxy)methyl)cyclohexane-2,3,4,5-tetrol 
• 171252-88-3 (1R,2R,3R,4S,5S)-4,5-di-O-acetyl-3-O-benzyl-5-((benzyloxy)methyl)cyclohexane-1,2,3,4,5-pentol 
• 183268-64-6 (1S,2R,3S,4S,5S)-1-azido-4,5-di-O-acetyl-3-O-benzyl-5-((benzyloxy)methyl)-2-O-(trifluoromethanesulfonyl)cyclohexane-2,3,4,5-tetrol 
• 171252-89-4 (1R,2S,3R,4S,5S)-4,5-di-O-acetyl-3-O-benzyl-5-((benzyloxy)methyl)-1-O-(trifluoromethanesulfonyl)cyclohexane-1,2,3,4,5-pentol 
• 171252-87-2 (1R,2S,3S,4S,5S)-4,5-di-O-acetyl-3-O-benzyl-5-((benzyloxy)methyl)-1,2-O-cyclohexylidenecyclohexane-1,2,3,4,5-pentol 
• 183268-55-5 (1R,2R,3S,4S,5S)-3-O-benzyl-5-((benzyloxy)methyl)-1,2-O-cyclohexylidenecyclohexane-1,2,3,4,5-pentol 
• 171252-92-9 (3R,4S,5S)-4,5-O-acetyl-3-O-benzyl-5-((benzyloxy)methyl)-1-cyclohexene-3,4,5-triol 
• 135735-90-9 (1R,2R,3S)-3-O-Benzyl-5-benzyloxymethyl-1,2-O-cyclohexylidene-cyclohex-4-en-1,2,3-triol 
• 171252-91-8 (1S,2S,3R,4S,5S)-1-azido-2,4,5-tri-O-acetyl-3-O-benzyl-5-((benzyloxy)methyl)cyclohexane-2,3,4,5-tetrol 

Downstream Products

• 83465-22-9 (1S,2S,3R,4S,5S)-1-amino-5-hydroxymethyl-2,3,4,5-tetrahydroxycyclohexane 

Relevant articles and documents

Facile syntheses of valiolamine and its diastereomers from (-)-quinic acid.1 nucleophilic substitution reactions of 5-(hydroxymethyl)cyclohexane-1,2,3,4,5-pentol

Valiolamine (1), 1-epi-valiolamine (2), 2-epi-valiolamine (3), (1R,2R)-valiolamine (4), and 2-amino regioisomer 17 have been prepared from (-)-quinic acid (6) in 14 (8.4% overall yield), 13 (9.0%), 15 (4.3%), 17 steps (2.5%), and 12 steps (13%), respectively. Charged nucleophilic ring-openings of cyclic sulfate (1R,2S,3S,4S,5S)-4,5-di-O-acetyl-3-O-benzyl-5-(benzyloxymethyl)-1,2-O,O- sulfonylcyclohexane-1,2,3,4,5-pentol (11) occurred regioselectively at C-2, whereas the corresponding ring-openings of its (1S,2R)-diastereomer 34 proceeded preponderantly at C-1. (1R,2S,3R,4S,5S)-2,4,5-Tri-O-acetyl-3-O-benzyl-5-((benzyloxy)methyl)-1-O- (trifluoromethanesulfonyl)cyclohexane-1,2,3,4,5-pentol (24) underwent novel internal displacement spontaneously to form (1S,2S,3R,4S,5S)-1,2,4-tri-O-acetyl-3-O-benzyl-5-((benzyloxy)methyl)cyclohexane- 1,2,3,4,5-pentol (25), whereas its 2-epimer was inert under the same conditions. Ruthenium-catalyzed dihydroxylation of alkene, (3R,4S,5S)-4,5-O-acetyl-3-O-benzyl-5-((benzyloxy)methyl)-1-cyclohexene-3,4,5- triol (31), gave the desired β-1,2-diol 32 in higher yield and stereoselectivity than the osmium tetraoxide protocol. The regioselectivity of charged nucleophilic ring-openings of cyclic sulfates 11, 34, and 38 is discussed.