(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

Base Information

Chemical Name:(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
CAS No.:862846-98-8
Molecular Formula:C₄₂H₆₂O₄Si₂
Molecular Weight:687.123
Hs Code.:

(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

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 13 articles about (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 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%

: 862846-93-3
(4S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-4-isopropyl-3-methyl-cyclopent-2-enone

: 862846-97-7
tert-Butyl-[(4R,7R)-7-(2-iodo-ethyl)-7-methyl-4,5,6,7-tetrahydro-isobenzofuran-4-yloxy]-diphenyl-silane

: 862846-98-8
(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

Guidance literature:: With boron trifluoride diethyl etherate; tert.-butyl lithium; thien-2-yl(cyano)copper lithium; In tetrahydrofuran; diethyl ether; pentane; at -78 - -40 ℃; for 1h;
DOI:10.1021/ol047387l

Reference yield:

: 59995-48-1
(R)-4-acetoxycyclopent-2-en-1-one

: 862846-98-8
(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

Guidance literature:: Multi-step reaction with 5 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

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; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; hexane; N,N-dimethyl-formamide; pentane; 2.2: Saegusa oxidation;
DOI:10.1021/ol047387l

Reference yield:

: 862846-91-1
(S)-4-Isopropyl-3-methyl-cyclopent-2-enone

: 862846-98-8
(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

Guidance literature:: Multi-step reaction with 3 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

With 1H-imidazole; n-butyllithium; (1R)-(?)-(10-camphorsulfonyl)oxaziridine; boron trifluoride diethyl etherate; tert.-butyl lithium; thien-2-yl(cyano)copper lithium; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; hexane; N,N-dimethyl-formamide; pentane;
DOI:10.1021/ol047387l