(R)-2-((2R,5S,6R)-6-{(E)-4-Benzenesulfonyl-4-[(1S,3aR,4S,5R,7aS)-4-(tert-butyl-dimethyl-silanyloxymethyl)-1-ethyl-2,3,3a,4,5,7a-hexahydro-1H-inden-5-yl]-1-ethyl-but-1-enyl}-5-methyl-tetrahydro-pyran-2-yl)-propionic acid methyl ester

Base Information

• Chemical Name: (R)-2-((2R,5S,6R)-6-{(E)-4-Benzenesulfonyl-4-[(1S,3aR,4S,5R,7aS)-4-(tert-butyl-dimethyl-silanyloxymethyl)-1-ethyl-2,3,3a,4,5,7a-hexahydro-1H-inden-5-yl]-1-ethyl-but-1-enyl}-5-methyl-tetrahydro-pyran-2-yl)-propionic acid methyl ester
• CAS No.: 80109-54-2
• Molecular Formula: C₄₀H₆₄O₆SSi
• Molecular Weight: 701.096
• Mol file: 80109-54-2.mol

Synonyms:(R)-2-((2R,5S,6R)-6-{(E)-4-Benzenesulfonyl-4-[(1S,3aR,4S,5R,7aS)-4-(tert-butyl-dimethyl-silanyloxymethyl)-1-ethyl-2,3,3a,4,5,7a-hexahydro-1H-inden-5-yl]-1-ethyl-but-1-enyl}-5-methyl-tetrahydro-pyran-2-yl)-propionic acid methyl ester

Chemical Property of (R)-2-((2R,5S,6R)-6-{(E)-4-Benzenesulfonyl-4-[(1S,3aR,4S,5R,7aS)-4-(tert-butyl-dimethyl-silanyloxymethyl)-1-ethyl-2,3,3a,4,5,7a-hexahydro-1H-inden-5-yl]-1-ethyl-but-1-enyl}-5-methyl-tetrahydro-pyran-2-yl)-propionic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2-((2R,5S,6R)-6-{(E)-4-Benzenesulfonyl-4-[(1S,3aR,4S,5R,7aS)-4-(tert-butyl-dimethyl-silanyloxymethyl)-1-ethyl-2,3,3a,4,5,7a-hexahydro-1H-inden-5-yl]-1-ethyl-but-1-enyl}-5-methyl-tetrahydro-pyran-2-yl)-propionic acid methyl ester

There total 75 articles about (R)-2-((2R,5S,6R)-6-{(E)-4-Benzenesulfonyl-4-[(1S,3aR,4S,5R,7aS)-4-(tert-butyl-dimethyl-silanyloxymethyl)-1-ethyl-2,3,3a,4,5,7a-hexahydro-1H-inden-5-yl]-1-ethyl-but-1-enyl}-5-methyl-tetrahydro-pyran-2-yl)-propionic acid methyl ester 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:

(+/-)-tert-butyl<<(1S,3aR,4S,5R,7aS)-1-ethyl-3a,4,5,7a-tetrahydro-5-<(phenylsulfonyl)methyl>-4-indanyl>methoxy>dimethylsilane (95588-48-0) + (R)-2-[(2R,5S,6R)-6-((E)-3-Bromo-1-ethyl-propenyl)-5-methyl-tetrahydro-pyran-2-yl]-propionic acid methyl ester (80109-51-9) → (R)-2-((2R,5S,6R)-6-{(E)-4-Benzenesulfonyl-4-[(1S,3aR,4S,5R,7aS)-4-(tert-butyl-dimethyl-silanyloxymethyl)-1-ethyl-2,3,3a,4,5,7a-hexahydro-1H-inden-5-yl]-1-ethyl-but-1-enyl}-5-methyl-tetrahydro-pyran-2-yl)-propionic acid methyl ester (80109-54-2) + (R)-2-((2R,5S,6R)-6-{(E)-4-Benzenesulfonyl-4-[(1R,3aS,4R,5S,7aR)-4-(tert-butyl-dimethyl-silanyloxymethyl)-1-ethyl-2,3,3a,4,5,7a-hexahydro-1H-inden-5-yl]-1-ethyl-but-1-enyl}-5-methyl-tetrahydro-pyran-2-yl)-propionic acid methyl ester (80109-54-2)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 0.5h; Yield given;

DOI:10.1021/ja00413a037

Reference yield:

(+/-)-tert-butyl<<(1S,3aR,4S,5R,7aS)-1-ethyl-3a,4,5,7a-tetrahydro-5-<(phenylsulfonyl)methyl>-4-indanyl>methoxy>dimethylsilane (95588-48-0) + (R)-2-[(2R,5S,6R)-6-((E)-3-Bromo-1-ethyl-propenyl)-5-methyl-tetrahydro-pyran-2-yl]-propionic acid methyl ester (80109-51-9) → (R)-2-((2R,5S,6R)-6-{(E)-4-Benzenesulfonyl-4-[(1S,3aR,4S,5R,7aS)-4-(tert-butyl-dimethyl-silanyloxymethyl)-1-ethyl-2,3,3a,4,5,7a-hexahydro-1H-inden-5-yl]-1-ethyl-but-1-enyl}-5-methyl-tetrahydro-pyran-2-yl)-propionic acid methyl ester (80109-54-2) + (R)-2-((2R,5S,6R)-6-{(E)-4-Benzenesulfonyl-4-[(1R,3aS,4R,5S,7aR)-4-(tert-butyl-dimethyl-silanyloxymethyl)-1-ethyl-2,3,3a,4,5,7a-hexahydro-1H-inden-5-yl]-1-ethyl-but-1-enyl}-5-methyl-tetrahydro-pyran-2-yl)-propionic acid methyl ester (80109-54-2)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 0.5h; Yield given;

DOI:10.1021/ja00413a037

Reference yield:

methyl (αR,2R,5S,6R)-tetrahydro-α,5-dimethyl-6-(1-oxopropyl)-2H-pyran-2-acetate (76566-84-2) → (R)-2-((2R,5S,6R)-6-{(E)-4-Benzenesulfonyl-4-[(1S,3aR,4S,5R,7aS)-4-(tert-butyl-dimethyl-silanyloxymethyl)-1-ethyl-2,3,3a,4,5,7a-hexahydro-1H-inden-5-yl]-1-ethyl-but-1-enyl}-5-methyl-tetrahydro-pyran-2-yl)-propionic acid methyl ester (80109-54-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / tetrahydrofuran / -78 °C

2: 65 percent / PBr₃ / diethyl ether / -10 °C

3: 1.) LDA, 2.) HMPA / 1.) THF, hexane, -78 deg C, 10 min, 2.) THF, hexane, -78 deg C, 25 min

With N,N,N,N,N,N-hexamethylphosphoric triamide; phosphorus tribromide; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether;

DOI:10.1021/jo00209a017

upstream raw materials:

(+/-)-tert-butyl<<(1S,3aR,4S,5R,7aS)-1-ethyl-3a,4,5,7a-tetrahydro-5-<(phenylsulfonyl)methyl>-4-indanyl>methoxy>dimethylsilane

(R)-2-[(2R,5S,6R)-6-((E)-3-Bromo-1-ethyl-propenyl)-5-methyl-tetrahydro-pyran-2-yl]-propionic acid methyl ester

tert-butyl<<(1S,3aR,4S,5R,7aS)-1-ethyl-3a,4,5,7a-tetrahydro-5-<(phenylsulfonyl)methyl>-4-indanyl>methoxy>dimethylsilane

3,4,5,6-tetrahydro-2H-pyran-2-one

Downstream raw materials:

antibiotic X-14547 A