(R)-2-Benzenesulfonyl-1-((3aR,5S,6aR)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-3-methyl-pent-4-en-1-one

Base Information

• Chemical Name: (R)-2-Benzenesulfonyl-1-((3aR,5S,6aR)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-3-methyl-pent-4-en-1-one
• CAS No.: 221372-49-2
• Molecular Formula: C₁₉H₂₄O₆S
• Molecular Weight: 380.462
• Mol file: 221372-49-2.mol

Synonyms:(R)-2-Benzenesulfonyl-1-((3aR,5S,6aR)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-3-methyl-pent-4-en-1-one

Chemical Property of (R)-2-Benzenesulfonyl-1-((3aR,5S,6aR)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-3-methyl-pent-4-en-1-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2-Benzenesulfonyl-1-((3aR,5S,6aR)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-3-methyl-pent-4-en-1-one

There total 5 articles about (R)-2-Benzenesulfonyl-1-((3aR,5S,6aR)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-3-methyl-pent-4-en-1-one 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: 79.0%

(3aR,5S,6aR)-2,2-Dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-5-carboxylic acid methyl ester (126694-09-5) + ((R)-2-Methyl-but-3-ene-1-sulfonyl)-benzene (126694-08-4) → (R)-2-Benzenesulfonyl-1-((3aR,5S,6aR)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-3-methyl-pent-4-en-1-one (221372-49-2)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; 1.) -78 deg C, 40 min, 2.) -78 deg C, 4 h;

DOI:10.1002/(SICI)1521-3765(19990201)5:2<599::AID-CHEM599>3.0.CO;2-N

Reference yield:

diphenyldisulfane (882-33-7) → (R)-2-Benzenesulfonyl-1-((3aR,5S,6aR)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-3-methyl-pent-4-en-1-one (221372-49-2)

Guidance literature:

Multi-step reaction with 5 steps

1: nBu₃P / dimethylformamide / 5 h / 0 - 25 °C

2: DIBAL / CH₂Cl₂; hexane / 0.5 h / -78 °C

3: 91 percent / NaN(SiMe₃)2 / tetrahydrofuran / 0.5 h / 0 °C

4: 82 percent / mCPBA / CH₂Cl₂ / 1.5 h / 0 °C

5: 79 percent / n-BuLi / hexane; tetrahydrofuran / 1.) -78 deg C, 40 min, 2.) -78 deg C, 4 h

With n-butyllithium; tributylphosphine; sodium hexamethyldisilazane; diisobutylaluminium hydride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/(SICI)1521-3765(19990201)5:2<599::AID-CHEM599>3.0.CO;2-N

Reference yield:

(R)-2-methyl-3-(phenylsulfanyl)propanoic acid methyl ester (165457-66-9) → (R)-2-Benzenesulfonyl-1-((3aR,5S,6aR)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-3-methyl-pent-4-en-1-one (221372-49-2)

Guidance literature:

Multi-step reaction with 4 steps

1: DIBAL / CH₂Cl₂; hexane / 0.5 h / -78 °C

2: 91 percent / NaN(SiMe₃)2 / tetrahydrofuran / 0.5 h / 0 °C

3: 82 percent / mCPBA / CH₂Cl₂ / 1.5 h / 0 °C

4: 79 percent / n-BuLi / hexane; tetrahydrofuran / 1.) -78 deg C, 40 min, 2.) -78 deg C, 4 h

With n-butyllithium; sodium hexamethyldisilazane; diisobutylaluminium hydride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1002/(SICI)1521-3765(19990201)5:2<599::AID-CHEM599>3.0.CO;2-N

upstream raw materials:

(3aR,5S,6aR)-2,2-Dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-5-carboxylic acid methyl ester

((R)-2-Methyl-but-3-ene-1-sulfonyl)-benzene

diphenyldisulfane

(R)-2-methyl-3-(phenylsulfanyl)propanoic acid methyl ester

Downstream raw materials:

(3S,5S,6S,8R)-6,8-Bis-benzyloxy-9,9-bis-ethylsulfanyl-3,5-dimethyl-non-1-en-5-ol

1-[(2S,3R,5S,6R)-3,5-Bis-benzyloxy-6-methyl-6-((S)-2-methyl-but-3-enyl)-tetrahydro-pyran-2-yl]-propan-2-one

(3R,5S,6R)-3,5-Bis-benzyloxy-6-methyl-6-((S)-2-methyl-but-3-enyl)-tetrahydro-pyran-2-ol

(S)-5-{(2R,3S,5R,6S)-3,5-Bis-benzyloxy-6-[3-benzyloxycarbonyl-2-(tert-butyl-dimethyl-silanyloxy)-2-methyl-propyl]-2-methyl-tetrahydro-pyran-2-yl}-3-(tert-butyl-dimethyl-silanyloxy)-4-methyl-pentanoic acid benzyl ester