(4S,7R)-4-{2-[(1S,4R,5S)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-5-isopropyl-1-methyl-cyclopent-2-enyl]-ethyl}-7-(tert-butyl-diphenyl-silanyloxy)-4-methyl-4,5,6,7-tetrahydro-isobenzofuran

Base Information

• Chemical Name: (4S,7R)-4-{2-[(1S,4R,5S)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-5-isopropyl-1-methyl-cyclopent-2-enyl]-ethyl}-7-(tert-butyl-diphenyl-silanyloxy)-4-methyl-4,5,6,7-tetrahydro-isobenzofuran
• CAS No.: 862846-99-9
• Molecular Formula: C₄₈H₇₆O₄Si₃
• Molecular Weight: 801.386
• Mol file: 862846-99-9.mol

Synonyms:(4S,7R)-4-{2-[(1S,4R,5S)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-5-isopropyl-1-methyl-cyclopent-2-enyl]-ethyl}-7-(tert-butyl-diphenyl-silanyloxy)-4-methyl-4,5,6,7-tetrahydro-isobenzofuran

Chemical Property of (4S,7R)-4-{2-[(1S,4R,5S)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-5-isopropyl-1-methyl-cyclopent-2-enyl]-ethyl}-7-(tert-butyl-diphenyl-silanyloxy)-4-methyl-4,5,6,7-tetrahydro-isobenzofuran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,7R)-4-{2-[(1S,4R,5S)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-5-isopropyl-1-methyl-cyclopent-2-enyl]-ethyl}-7-(tert-butyl-diphenyl-silanyloxy)-4-methyl-4,5,6,7-tetrahydro-isobenzofuran

There total 15 articles about (4S,7R)-4-{2-[(1S,4R,5S)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-5-isopropyl-1-methyl-cyclopent-2-enyl]-ethyl}-7-(tert-butyl-diphenyl-silanyloxy)-4-methyl-4,5,6,7-tetrahydro-isobenzofuran 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: 93.0%

(2R,3S,4R)-2-(tert-Butyl-dimethyl-silanyloxy)-4-{2-[(4S,7R)-7-(tert-butyl-diphenyl-silanyloxy)-4-methyl-4,5,6,7-tetrahydro-isobenzofuran-4-yl]-ethyl}-3-isopropyl-4-methyl-cyclopentanone (862846-98-8) + t-butyldimethylsiyl triflate (69739-34-0) → (4S,7R)-4-{2-[(1S,4R,5S)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-5-isopropyl-1-methyl-cyclopent-2-enyl]-ethyl}-7-(tert-butyl-diphenyl-silanyloxy)-4-methyl-4,5,6,7-tetrahydro-isobenzofuran (862846-99-9)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; hexane; at -78 - 20 ℃;

DOI:10.1021/ol047387l

Reference yield:

(R)-4-acetoxycyclopent-2-en-1-one (59995-48-1) → (4S,7R)-4-{2-[(1S,4R,5S)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-5-isopropyl-1-methyl-cyclopent-2-enyl]-ethyl}-7-(tert-butyl-diphenyl-silanyloxy)-4-methyl-4,5,6,7-tetrahydro-isobenzofuran (862846-99-9)

Guidance literature:

Multi-step reaction with 6 steps

1.1: TMSCl; CuBr*DMS; HMPA / tetrahydrofuran / -78 - -40 °C

1.2: (1R)-10-camphorsulfonic acid / CH₂Cl₂ / 20 h / Heating

2.1: CuI; TMSCl / diethyl ether / 17 h / -40 - 20 °C

2.2: Pd(OAc)2 / acetonitrile / 9 h / 20 °C

3.1: 724 mg / (i-Pr)2NEt; n-BuLi; (1R)-(10-camphorsulfonyl)oxaziridine / tetrahydrofuran; hexane / -78 - -30 °C

4.1: 81 percent / imidazole / dimethylformamide / 16.17 h / 0 - 20 °C

5.1: 50 percent / t-BuLi; (2-thienyl)Cu(CN)Li; BF₃*Et₂O / pentane; diethyl ether; tetrahydrofuran / 1 h / -78 - -40 °C

6.1: 93 percent / LDA; HMPA; Et₃N / tetrahydrofuran; hexane / -78 - 20 °C

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; copper(l) iodide; n-butyllithium; chloro-trimethyl-silane; copper(I) bromide dimethylsulfide complex; (1R)-(?)-(10-camphorsulfonyl)oxaziridine; boron trifluoride diethyl etherate; tert.-butyl lithium; thien-2-yl(cyano)copper lithium; triethylamine; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; hexane; N,N-dimethyl-formamide; pentane; 2.2: Saegusa oxidation;

DOI:10.1021/ol047387l

Reference yield:

(S)-4-Isopropyl-3-methyl-cyclopent-2-enone (862846-91-1) → (4S,7R)-4-{2-[(1S,4R,5S)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-5-isopropyl-1-methyl-cyclopent-2-enyl]-ethyl}-7-(tert-butyl-diphenyl-silanyloxy)-4-methyl-4,5,6,7-tetrahydro-isobenzofuran (862846-99-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 724 mg / (i-Pr)2NEt; n-BuLi; (1R)-(10-camphorsulfonyl)oxaziridine / tetrahydrofuran; hexane / -78 - -30 °C

2: 81 percent / imidazole / dimethylformamide / 16.17 h / 0 - 20 °C

3: 50 percent / t-BuLi; (2-thienyl)Cu(CN)Li; BF₃*Et₂O / pentane; diethyl ether; tetrahydrofuran / 1 h / -78 - -40 °C

4: 93 percent / LDA; HMPA; Et₃N / tetrahydrofuran; hexane / -78 - 20 °C

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; (1R)-(?)-(10-camphorsulfonyl)oxaziridine; boron trifluoride diethyl etherate; tert.-butyl lithium; thien-2-yl(cyano)copper lithium; triethylamine; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; hexane; N,N-dimethyl-formamide; pentane;

DOI:10.1021/ol047387l

upstream raw materials:

(2R,3S,4R)-2-(tert-Butyl-dimethyl-silanyloxy)-4-{2-[(4S,7R)-7-(tert-butyl-diphenyl-silanyloxy)-4-methyl-4,5,6,7-tetrahydro-isobenzofuran-4-yl]-ethyl}-3-isopropyl-4-methyl-cyclopentanone

t-butyldimethylsiyl triflate

(S)-4-Isopropyl-cyclopent-2-enone

(S)-4-Isopropyl-3-methyl-cyclopent-2-enone

Downstream raw materials:

(2R,3R,5aS,7aS,8S,9R,10aR,10bS)-9-(tert-Butyl-dimethyl-silanyloxy)-3-(tert-butyl-diphenyl-silanyloxy)-8-isopropyl-2-methoxy-5a,7a-dimethyl-2,3,4,5,5a,6,7,7a,8,9,10a,10b-dodecahydro-1-oxa-benzo[cd]cyclopenta[h]azulen-10-one