(1R,2R,3S,4S,5S)-4-O-acetyl-5-(benzoyloxymethyl)-3-O-(tert-butyldimethylsilyl)-1,2-O-cyclohexylidenecyclohexane-1,2,3,4,5-pentol

Base Information

Chemical Name:(1R,2R,3S,4S,5S)-4-O-acetyl-5-(benzoyloxymethyl)-3-O-(tert-butyldimethylsilyl)-1,2-O-cyclohexylidenecyclohexane-1,2,3,4,5-pentol
CAS No.:175979-28-9
Molecular Formula:C₂₈H₄₂O₈Si
Molecular Weight:534.722
Hs Code.:

Synonyms:(1R,2R,3S,4S,5S)-4-O-acetyl-5-(benzoyloxymethyl)-3-O-(tert-butyldimethylsilyl)-1,2-O-cyclohexylidenecyclohexane-1,2,3,4,5-pentol

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Chemical Property of (1R,2R,3S,4S,5S)-4-O-acetyl-5-(benzoyloxymethyl)-3-O-(tert-butyldimethylsilyl)-1,2-O-cyclohexylidenecyclohexane-1,2,3,4,5-pentol

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Technology Process of (1R,2R,3S,4S,5S)-4-O-acetyl-5-(benzoyloxymethyl)-3-O-(tert-butyldimethylsilyl)-1,2-O-cyclohexylidenecyclohexane-1,2,3,4,5-pentol

There total 7 articles about (1R,2R,3S,4S,5S)-4-O-acetyl-5-(benzoyloxymethyl)-3-O-(tert-butyldimethylsilyl)-1,2-O-cyclohexylidenecyclohexane-1,2,3,4,5-pentol 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: 97.0%

: 108-24-7
acetic anhydride

: 174966-55-3
(1R,2S,3S,4R,5R)-3-O-tert-butyldimethylsilyl-1-benzoyloxymethyl-4,5-O-cyclohexylidene-1,2,3,4,5-cyclohexanepentaol

: 175979-28-9
(1R,2R,3S,4S,5S)-4-O-acetyl-5-(benzoyloxymethyl)-3-O-(tert-butyldimethylsilyl)-1,2-O-cyclohexylidenecyclohexane-1,2,3,4,5-pentol

Guidance literature:: With pyridine; dmap; In dichloromethane; Ambient temperature;
DOI:10.1016/0957-4166(96)00004-3

Reference yield:

: 130021-74-8
(1R,2R,3S)-1,2-O-Cyclohexylidene-5-hydroxymethyl-4-cyclohexen-1,2,3-triol

: 175979-28-9
(1R,2R,3S,4S,5S)-4-O-acetyl-5-(benzoyloxymethyl)-3-O-(tert-butyldimethylsilyl)-1,2-O-cyclohexylidenecyclohexane-1,2,3,4,5-pentol

Guidance literature:: Multi-step reaction with 4 steps

1: 82 percent / collidine / CH₂Cl₂ / 2 h / -78 - 25 °C

2: 97 percent / imidazole, DMAP / CH₂Cl₂ / 12 h / Ambient temperature

3: 75 percent / RuCl₃, NaIO₄ / ethyl acetate; acetonitrile / 0.05 h / 0 °C

4: 97 percent / DMAP / pyridine; CH₂Cl₂ / 12 h / Ambient temperature

With 1H-imidazole; 2,3,5-trimethyl-pyridine; dmap; ruthenium trichloride; sodium periodate; In pyridine; dichloromethane; ethyl acetate; acetonitrile;
DOI:10.1021/jo970907o

Reference yield:

: 203317-81-1
(1R,2R,3S)-5-(benzoyloxymethyl)-1,2-O-cyclohexylidene-4-cyclohexene-1,2,3-triol

: 175979-28-9
(1R,2R,3S,4S,5S)-4-O-acetyl-5-(benzoyloxymethyl)-3-O-(tert-butyldimethylsilyl)-1,2-O-cyclohexylidenecyclohexane-1,2,3,4,5-pentol

Guidance literature:: Multi-step reaction with 3 steps

1: 97 percent / imidazole, DMAP / CH₂Cl₂ / 12 h / Ambient temperature

2: 75 percent / RuCl₃, NaIO₄ / ethyl acetate; acetonitrile / 0.05 h / 0 °C

3: 97 percent / DMAP / pyridine; CH₂Cl₂ / 12 h / Ambient temperature

With 1H-imidazole; dmap; ruthenium trichloride; sodium periodate; In pyridine; dichloromethane; ethyl acetate; acetonitrile;
DOI:10.1021/jo970907o