(+)-(1R,2R,3S,4S)-1-hydroxy-2,3,4-triacetoxy-5-cyclohexene

Base Information

• Chemical Name: (+)-(1R,2R,3S,4S)-1-hydroxy-2,3,4-triacetoxy-5-cyclohexene
• CAS No.: 133319-95-6
• Molecular Formula: C₁₂H₁₆O₇
• Molecular Weight: 272.255
• Mol file: 133319-95-6.mol

Synonyms:

Chemical Property of (+)-(1R,2R,3S,4S)-1-hydroxy-2,3,4-triacetoxy-5-cyclohexene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-(1R,2R,3S,4S)-1-hydroxy-2,3,4-triacetoxy-5-cyclohexene

There total 6 articles about (+)-(1R,2R,3S,4S)-1-hydroxy-2,3,4-triacetoxy-5-cyclohexene 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: 98.0%

(+)-(1S,5S,6S)-1,5,6-triacetoxy-4-oxocyclohex-2-ene (133319-94-5) → Acetic acid (1S,2S,6R)-2,6-diacetoxy-5-hydroxy-cyclohex-3-enyl ester (133218-73-2,133319-95-6)

Guidance literature:

With sodium tetrahydroborate; cerium(III) chloride; In methanol;

DOI:10.1039/c39910000061

Reference yield: 61.0%

meso-Conduritol D tetraacetate (123354-99-4) → (+)-(1R,2R,3S,4S)-1-hydroxy-2,3,4-triacetoxy-5-cyclohexene (133319-95-6)

Guidance literature:

With butan-1-ol; at 40 ℃; for 24h; lipase from porcine pancreas (PPL);

DOI:10.1016/0957-4166(96)00342-4

Reference yield:

cis-1,2-dihydroxy-3-fluorocyclohexa-3,5-diene (131101-27-4) → Acetic acid (1S,2S,6R)-2,6-diacetoxy-5-hydroxy-cyclohex-3-enyl ester (133218-73-2,133319-95-6)

Guidance literature:

Multi-step reaction with 4 steps

1: m-chloroperoxybenzoic acid / CH₂Cl₂ / 0 °C

2: 50 percent / aq. trifluoroacetic acid / acetone

3: 80 percent / pyridine / 18 h / 0 °C

4: 98 percent / NaBH₄-CeCl₃ / methanol

With pyridine; sodium tetrahydroborate; cerium(III) chloride; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In methanol; dichloromethane; acetone;

DOI:10.1039/c39910000061

upstream raw materials:

(+)-(1S,5S,6S)-1,5,6-triacetoxy-4-oxocyclohex-2-ene

(4S,5S,6S)-4,5,6-trihydroxycyclohex-2-enone

(1S,2S,3R,4S)-1-Fluoro-7-oxa-bicyclo[2.2.1]hept-5-ene-2,3-diol

cis-1,2-dihydroxy-3-fluorocyclohexa-3,5-diene

Downstream raw materials:

(1S,2R,3S,4S)-5-cyclohexene-1,2,3,4-tetrol

(1R,2S,3S,6S)-6-Amino-cyclohex-4-ene-1,2,3-triol

(-)-(1S,2R,3S,4S)-1-benzoyloxy-2,3,4-triacetoxy-5-cyclohexene

(1S,2S,3R,4S)-1,2,3,4-tetra-O-acetylconduritol C