(2RS,4S,2'R)-2'-tert-butyldimethylsilyloxydec-9-en-1-yl-2-(phenylsulfanyl)pentan-1,4-olide

Base Information

• Chemical Name: (2RS,4S,2'R)-2'-tert-butyldimethylsilyloxydec-9-en-1-yl-2-(phenylsulfanyl)pentan-1,4-olide
• CAS No.: 303053-04-5
• Molecular Formula: C₂₇H₄₄O₃SSi
• Molecular Weight: 476.796
• Mol file: 303053-04-5.mol

Synonyms:(2RS,4S,2'R)-2'-tert-butyldimethylsilyloxydec-9-en-1-yl-2-(phenylsulfanyl)pentan-1,4-olide

Chemical Property of (2RS,4S,2'R)-2'-tert-butyldimethylsilyloxydec-9-en-1-yl-2-(phenylsulfanyl)pentan-1,4-olide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2RS,4S,2'R)-2'-tert-butyldimethylsilyloxydec-9-en-1-yl-2-(phenylsulfanyl)pentan-1,4-olide

There total 5 articles about (2RS,4S,2'R)-2'-tert-butyldimethylsilyloxydec-9-en-1-yl-2-(phenylsulfanyl)pentan-1,4-olide 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: 50.0%

(5S)-5-methyl-3-phenylsulfanyl-4,5-dihydrofuran-2(3H)-one (184435-75-4) + (2R)-2-tert-butyldimethylsilyloxy-1-iododec-9-ene → (2RS,4S,2'R)-2'-tert-butyldimethylsilyloxydec-9-en-1-yl-2-(phenylsulfanyl)pentan-1,4-olide (303053-04-5)

Guidance literature:

(5S)-5-methyl-3-phenylsulfanyl-4,5-dihydrofuran-2(3H)-one; With lithium diisopropyl amide; In tetrahydrofuran; for 0.5h; cooling;

(2R)-2-tert-butyldimethylsilyloxy-1-iododec-9-ene; With N,N,N,N,N,N-hexamethylphosphoric triamide; In tetrahydrofuran; at 20 ℃; for 16h; Further stages.;

DOI:10.1021/jo000500a

Reference yield:

1,10-decadiene (1647-16-1) → (2RS,4S,2'R)-2'-tert-butyldimethylsilyloxydec-9-en-1-yl-2-(phenylsulfanyl)pentan-1,4-olide (303053-04-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 75 percent / AD-mix-β / 2-methyl-propan-2-ol; H2O / 24 h / 0 °C

2.1: 70 percent / collidine / 16 h / 0 - 20 °C

3.1: 99 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / -78 °C

4.1: 95 percent / NaI; NaHCO₃ / acetone / 36 h / Heating

5.1: lithium diisopropylamide / tetrahydrofuran / 0.5 h / cooling

5.2: 50 percent / HMPA / tetrahydrofuran / 16 h / 20 °C

With 2,6-dimethylpyridine; 2,3,5-trimethyl-pyridine; AD-mix-β; sodium hydrogencarbonate; sodium iodide; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; water; acetone; tert-butyl alcohol; 1.1: Sharpless hydroxylation / 2.1: Tosylation / 3.1: Substitution / 4.1: Substitution / 5.1: deprotonation / 5.2: Substitution;

DOI:10.1021/jo000500a

Reference yield:

(2R)-dec-2-ene-1,2-diol → (2RS,4S,2'R)-2'-tert-butyldimethylsilyloxydec-9-en-1-yl-2-(phenylsulfanyl)pentan-1,4-olide (303053-04-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 70 percent / collidine / 16 h / 0 - 20 °C

2.1: 99 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / -78 °C

3.1: 95 percent / NaI; NaHCO₃ / acetone / 36 h / Heating

4.1: lithium diisopropylamide / tetrahydrofuran / 0.5 h / cooling

4.2: 50 percent / HMPA / tetrahydrofuran / 16 h / 20 °C

With 2,6-dimethylpyridine; 2,3,5-trimethyl-pyridine; sodium hydrogencarbonate; sodium iodide; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; acetone; 1.1: Tosylation / 2.1: Substitution / 3.1: Substitution / 4.1: deprotonation / 4.2: Substitution;

DOI:10.1021/jo000500a

upstream raw materials:

(5S)-5-methyl-3-phenylsulfanyl-4,5-dihydrofuran-2(3H)-one

1,10-decadiene

Downstream raw materials:

(+)-asimicin