(3R,4S,5S)-4,5-O-acetyl-3-O-benzyl-5-((benzyloxy)methyl)-1-cyclohexene-3,4,5-triol

Base Information

Chemical Name:(3R,4S,5S)-4,5-O-acetyl-3-O-benzyl-5-((benzyloxy)methyl)-1-cyclohexene-3,4,5-triol
CAS No.:171252-92-9
Molecular Formula:C₂₅H₂₈O₆
Molecular Weight:424.494
Hs Code.:

Synonyms:(3R,4S,5S)-4,5-O-acetyl-3-O-benzyl-5-((benzyloxy)methyl)-1-cyclohexene-3,4,5-triol

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Chemical Property of (3R,4S,5S)-4,5-O-acetyl-3-O-benzyl-5-((benzyloxy)methyl)-1-cyclohexene-3,4,5-triol

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Technology Process of (3R,4S,5S)-4,5-O-acetyl-3-O-benzyl-5-((benzyloxy)methyl)-1-cyclohexene-3,4,5-triol

There total 4 articles about (3R,4S,5S)-4,5-O-acetyl-3-O-benzyl-5-((benzyloxy)methyl)-1-cyclohexene-3,4,5-triol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: 135735-90-9
(1R,2R,3S)-3-O-Benzyl-5-benzyloxymethyl-1,2-O-cyclohexylidene-cyclohex-4-en-1,2,3-triol

: 171252-92-9
(3R,4S,5S)-4,5-O-acetyl-3-O-benzyl-5-((benzyloxy)methyl)-1-cyclohexene-3,4,5-triol

Guidance literature:: Multi-step reaction with 4 steps

1: 75 percent / Me₃NO, OsO₄ / 2-methyl-propan-2-ol; pyridine; H₂O / 12 h / Heating

2: 90 percent / DMAP / triethylamine / 3 h / Heating

3: 90 percent / TFA, H₂O / CH₂Cl₂ / 24 h / Ambient temperature

4: 1.) 1,1'-(thiocarbonyl)diimidazole, 2.) P(OMe)3 / 1.) toluene, 90 deg C, 1.5 h; reflux, overnight, 2.) reflux, 24 h

With dmap; osmium(VIII) oxide; trimethylamine-N-oxide; water; 1,1'-Thiocarbonyldiimidazole; trifluoroacetic acid; phosphorous acid trimethyl ester; In pyridine; dichloromethane; water; triethylamine; tert-butyl alcohol;
DOI:10.1021/jo9607828

Reference yield:

: 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

: 171252-92-9
(3R,4S,5S)-4,5-O-acetyl-3-O-benzyl-5-((benzyloxy)methyl)-1-cyclohexene-3,4,5-triol

Guidance literature:: Multi-step reaction with 2 steps

1: 90 percent / TFA, H₂O / CH₂Cl₂ / 24 h / Ambient temperature

2: 1.) 1,1'-(thiocarbonyl)diimidazole, 2.) P(OMe)3 / 1.) toluene, 90 deg C, 1.5 h; reflux, overnight, 2.) reflux, 24 h

With water; 1,1'-Thiocarbonyldiimidazole; trifluoroacetic acid; phosphorous acid trimethyl ester; In dichloromethane;
DOI:10.1021/jo9607828

Reference yield:

: 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

Guidance literature:: Multi-step reaction with 3 steps

1: 90 percent / DMAP / triethylamine / 3 h / Heating

2: 90 percent / TFA, H₂O / CH₂Cl₂ / 24 h / Ambient temperature

3: 1.) 1,1'-(thiocarbonyl)diimidazole, 2.) P(OMe)3 / 1.) toluene, 90 deg C, 1.5 h; reflux, overnight, 2.) reflux, 24 h

With dmap; water; 1,1'-Thiocarbonyldiimidazole; trifluoroacetic acid; phosphorous acid trimethyl ester; In dichloromethane; triethylamine;
DOI:10.1021/jo9607828