(1S,2R,3S,6S)-6-(phenylthio)-2,3-isopropylidendioxy-4-bromocyclohex-4-en-1-ol

Base Information

• Chemical Name: (1S,2R,3S,6S)-6-(phenylthio)-2,3-isopropylidendioxy-4-bromocyclohex-4-en-1-ol
• CAS No.: 885050-19-1
• Molecular Formula: C₁₅H₁₇BrO₃S
• Molecular Weight: 357.268
• Mol file: 885050-19-1.mol

Synonyms:(1S,2R,3S,6S)-6-(phenylthio)-2,3-isopropylidendioxy-4-bromocyclohex-4-en-1-ol

Chemical Property of (1S,2R,3S,6S)-6-(phenylthio)-2,3-isopropylidendioxy-4-bromocyclohex-4-en-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2R,3S,6S)-6-(phenylthio)-2,3-isopropylidendioxy-4-bromocyclohex-4-en-1-ol

There total 5 articles about (1S,2R,3S,6S)-6-(phenylthio)-2,3-isopropylidendioxy-4-bromocyclohex-4-en-1-ol 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: 78.0%

(1S,2S,5R,6R)-3-bromo-5,6-epoxy-1,2-O-isopropylidencyclohex-3-en-1,2-diol (130669-74-8) + thiophenol (108-98-5) → (1S,2R,3S,6R)-6-(phenylthio)-2,3-isopropylidendioxy-4-bromocyclohex-4-en-1-ol + (1S,2R,3S,6S)-6-(phenylthio)-2,3-isopropylidendioxy-4-bromocyclohex-4-en-1-ol (885050-19-1)

Guidance literature:

With ytterbium(III) triflate; In toluene; at 20 ℃; for 1h;

DOI:10.1016/j.tetasy.2006.01.024

Reference yield:

bromobenzene (108-86-1,52753-63-6) → (1S,2R,3S,6S)-6-(phenylthio)-2,3-isopropylidendioxy-4-bromocyclohex-4-en-1-ol (885050-19-1)

Guidance literature:

Multi-step reaction with 4 steps

1: Pseudomonas putida F₃₉/D

2: 98 percent / p-TsOH / acetone / 0.5 h / 20 °C

3: 85 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 20 °C

4: 78 percent / Yb(OTf)3 / toluene / 1 h / 20 °C

With Pseudomonas putida F₃₉/D; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; ytterbium(III) triflate; In dichloromethane; acetone; toluene;

DOI:10.1016/j.tetasy.2006.01.024

Reference yield:

(3aS,7aS)-4-bromo-2,2-dimethyl-3a,7a-dihydro-1,3-benzodioxole (130669-75-9) → (1S,2R,3S,6S)-6-(phenylthio)-2,3-isopropylidendioxy-4-bromocyclohex-4-en-1-ol (885050-19-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 20 °C

2: 78 percent / Yb(OTf)3 / toluene / 1 h / 20 °C

With 3-chloro-benzenecarboperoxoic acid; ytterbium(III) triflate; In dichloromethane; toluene;

DOI:10.1016/j.tetasy.2006.01.024

upstream raw materials:

(1S,2S,5R,6R)-3-bromo-5,6-epoxy-1,2-O-isopropylidencyclohex-3-en-1,2-diol

toluene-4-sulfonic acid

thiophenol

bromobenzene

Downstream raw materials:

(1S,2R, 3S,6S)-4-bromo-6-(phenylthio)cyclohexene-1,2,3-triol

(1S,2R,3R,6S)-6-(phenylthio)-2,3-isopropylidendioxycyclohex-4-en-1-ol