(1R,2S,3S,4R)-3-Methoxy-2-[(2R,3R)-2-methyl-3-(3-methyl-but-2-enyl)-oxiranyl]-1-phenylsulfanylmethyl-cyclohexane-1,4-diol

Base Information

• Chemical Name: (1R,2S,3S,4R)-3-Methoxy-2-[(2R,3R)-2-methyl-3-(3-methyl-but-2-enyl)-oxiranyl]-1-phenylsulfanylmethyl-cyclohexane-1,4-diol
• CAS No.: 135149-67-6
• Molecular Formula: C₂₂H₃₂O₄S
• Molecular Weight: 392.56
• Mol file: 135149-67-6.mol

Synonyms:(1R,2S,3S,4R)-3-Methoxy-2-[(2R,3R)-2-methyl-3-(3-methyl-but-2-enyl)-oxiranyl]-1-phenylsulfanylmethyl-cyclohexane-1,4-diol

Chemical Property of (1R,2S,3S,4R)-3-Methoxy-2-[(2R,3R)-2-methyl-3-(3-methyl-but-2-enyl)-oxiranyl]-1-phenylsulfanylmethyl-cyclohexane-1,4-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2S,3S,4R)-3-Methoxy-2-[(2R,3R)-2-methyl-3-(3-methyl-but-2-enyl)-oxiranyl]-1-phenylsulfanylmethyl-cyclohexane-1,4-diol

There total 1 articles about (1R,2S,3S,4R)-3-Methoxy-2-[(2R,3R)-2-methyl-3-(3-methyl-but-2-enyl)-oxiranyl]-1-phenylsulfanylmethyl-cyclohexane-1,4-diol 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:

sodium thiophenolate (930-69-8) + fumagillol (35903-52-7,128656-25-7,132746-73-7,108102-51-8) → (1R,2S,3S,4R)-3-Methoxy-2-[(2R,3R)-2-methyl-3-(3-methyl-but-2-enyl)-oxiranyl]-1-phenylsulfanylmethyl-cyclohexane-1,4-diol (135149-67-6)

Guidance literature:

In N,N-dimethyl-formamide; at 20 ℃; for 2.5h;

DOI:10.1021/jm0341103

Reference yield:

(1R,2S,3S,4R)-3-Methoxy-2-[(2R,3R)-2-methyl-3-(3-methyl-but-2-enyl)-oxiranyl]-1-phenylsulfanylmethyl-cyclohexane-1,4-diol (135149-67-6) → (1R,2S,3S,4R)-1-Benzenesulfinylmethyl-3-methoxy-2-[(2R,3R)-2-methyl-3-(3-methyl-but-2-enyl)-oxiranyl]-cyclohexane-1,4-diol (592517-32-3)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In chloroform; at -78 ℃; for 1h;

DOI:10.1021/jm0341103

Reference yield:

(1R,2S,3S,4R)-3-Methoxy-2-[(2R,3R)-2-methyl-3-(3-methyl-but-2-enyl)-oxiranyl]-1-phenylsulfanylmethyl-cyclohexane-1,4-diol (135149-67-6) → Fumagalone

Guidance literature:

Multi-step reaction with 4 steps

1: mCPBA / CHCl₃ / 1 h / -78 °C

2: 59.1 percent / tetrapropylammonium perrhthenate; 4-methylmorpholine N-oxide / CH₂Cl₂ / 1 h / 20 °C

3: NaOAc / 1 h / 155 °C

4: 7.0 mg / aq. K₂CO₃ / CH₂Cl₂; methanol / 0.25 h / 20 °C

With tetrapropylammonium perruthennate; sodium acetate; potassium carbonate; 4-methylmorpholine N-oxide; 3-chloro-benzenecarboperoxoic acid; In methanol; dichloromethane; chloroform; 3: Pummerer rearrangement;

DOI:10.1021/jm0341103

upstream raw materials:

sodium thiophenolate

fumagillol

Downstream raw materials:

(1R,2S,3S,4R)-1-Benzenesulfinylmethyl-3-methoxy-2-[(2R,3R)-2-methyl-3-(3-methyl-but-2-enyl)-oxiranyl]-cyclohexane-1,4-diol

(2S,3S,4R)-4-Benzenesulfinylmethyl-4-hydroxy-2-methoxy-3-[(2R,3R)-2-methyl-3-(3-methyl-but-2-enyl)-oxiranyl]-cyclohexanone

Acetic acid {(1R,2S,3S)-1-hydroxy-3-methoxy-2-[(2R,3R)-2-methyl-3-(3-methyl-but-2-enyl)-oxiranyl]-4-oxo-cyclohexyl}-phenylsulfanyl-methyl ester