725268-38-2

Basic information

• Product Name: (2S,3R)-2,3-Bis-benzyloxy-5-hydroxy-cyclohexanone
• Synonyms: (2S,3R)-2,3-Bis-benzyloxy-5-hydroxy-cyclohexanone
• CAS NO: 725268-38-2
• Molecular Weight: 326.392
• Mol File: 725268-38-2.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (2S,3R)-2,3-Bis-benzyloxy-5-hydroxy-cyclohexanone(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3R)-2,3-Bis-benzyloxy-5-hydroxy-cyclohexanone(725268-38-2)
• EPA Substance Registry System: (2S,3R)-2,3-Bis-benzyloxy-5-hydroxy-cyclohexanone(725268-38-2)

Safety Data

• Hazardous Substances Data: 725268-38-2(Hazardous Substances Data)

Upstream product

• 189758-76-7 (2S,3S,4R,6S)-3,4-Bis-benzyloxy-2-bromomethyl-6-methoxy-tetrahydro-pyran 
• 69617-72-7 (3S,4S,5R,1'S)-3-bromo-5-(2'-bromo-1'-hydroxy)ethyl-4,5-dihydro-4-hydroxy-2-(3H)-furanone 
• 119943-96-3 Methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-arabino-hexopyranoside 
• 145149-85-5 Methyl 3,4-di-O-benzyl-2-deoxy-α-D-arabino-hexopyranoside 
• 6087-40-7 (2R,3S,4R,6S)-3,4-diacetoxy-2-(acetoxymethyl)-6-methoxytetrahydro-2H-pyran 
• 675128-76-4 (2R,3S,4R)-3,4-Bis-benzyloxy-6-methoxy-2-trityloxymethyl-tetrahydro-pyran 
• 675128-75-3 (2R,3S,4R)-6-Methoxy-2-trityloxymethyl-tetrahydro-pyran-3,4-diol 
• 675128-77-5 methyl 3,4-di-O-benzyl-2-deoxy-D-arabino-hexopyraboside 
• 160400-66-8 methyl 2-deoxy-D-arabinopyranoside 
• 126873-07-2 methyl 3,4,6-tri-O-acetyl-2-deoxy-α/β-D-glucopyranoside 
• 189758-77-8 methyl 3,4-di-O-benzyl-2-deoxy-5-methylene-α-D-xylopyranoside 
• 189758-74-5 (2S,3S,4R,6S)-2-Bromomethyl-6-methoxy-tetrahydro-pyran-3,4-diol 
• 122204-66-4 methyl 2,6-dibromo-2,6-dideoxy-α-D-mannopyranoside 
• 81927-55-1 O-benzyl 2,2,2-trichloroacetimidate 

Downstream Products

• 6272-38-4 O-benzylcatechol 
• 189758-78-9 GS 416 
• 81308-73-8 (3R,5R)-3,4,5-Tris-benzyloxy-cyclohexanone 
• 141404-08-2 (3R,5R)-3,5-bis[tert-butyl(dimethyl)silyloxy]-4-hydroxycyclohexanone 
• 141404-09-3 (3R,5R)-3,5-bis<(tert-butyldimethylsilyl)oxy>-4-<(trimethylsilyl)oxy>cyclohexanone 
• 95639-53-5 3(R),5(R)-trihydroxycyclohexanone 
• 506423-10-5 (3R,5R)-3,4,5-Tris-benzyloxy-cyclohexanol 
• 506423-08-1 (1R,2R,3R,5R)-2,3-Bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-cyclohexanol 
• 506423-07-0 (1R,2R,3R,5S)-2,3-Bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-cyclohexanol 
• 506423-09-2 tert-Butyl-dimethyl-((3R,5R)-3,4,5-tris-benzyloxy-cyclohexyloxy)-silane 

Relevant articles and documents

Synthetic studies on antascomicin A: Construction of the C18-C34 fragment

Stereoselective synthesis of the C18-C34 fragment of antascomicin A is described. Construction of the C27-C34 carbocycle moiety was achieved via catalytic Ferrier carbocylization and Johnson-Claisen rearrangement, which was converted to iodide 2 by use of

Synthesis of the 2-deoxyisomaltose analogue of acarbose by an improved route to chiral valieneamines

A 2-deoxyisomaltose analogue of acarbose was stereoselectively synthesised in 11 steps with a total yield of 7% starting from 2,6-dibromo-2,6-dideoxy-D-mannono-1,4-lactone (6). The latter was reduced to the lactol, converted to the methyl glycoside (7) and hydrogenated to the 6-bromo-2,6-dideoxyglycoside (8). Benzylation of the hydroxy groups, elimination of bromine to a 5-ene and Ferrier carbocyclisation gave (2S,3R)-2,3-bisbenzyloxycyclohex-5-enone (12). 1,2-addition of benzyloxymethyl lithium at -110 C gave a 6:1 mixture of tertiary alcohols 13; the (1S) isomer was the major one. Reaction with trichloroacetyl isocyanate gave a carbamate 19, which, when dehydrated to the cyanate, spontaneously underwent [1,3] sigmatropic rearrangement to an isocyanate, which on addition of methanol gave the methylcarbamate 20. Basic hydrolysis of this compound gave (2R,3R,5R)-5-amino-1-benzyloxy-methyl-2,3-bis(benzyloxy)cyclohex-6-ene (22), which could be deprotected to 2-deoxyvalieneamine (5). Reaction with 2-azidoethyl 2,3,4-tri-O-benzyl-6-O-triflyl-α-D-glucopyranoside (34) gave the secondary amine 35, which was completely de-O-protected with sodium in ammonia to give 6-deoxy-6-((1R,3R,4R)-3,4-dihydroxy-5-hydroxymethylcyclohex-5-enylamino)-D- glucose (4), the 2-deoxyisomaltose analogue of acarbose.