[(2R,3R,3aS,8bR)-2-(tert-Butyl-diphenyl-silanyloxy)-3-((E)-(S)-3-hydroxy-oct-1-enyl)-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-7-yl]-acetic acid methyl ester

Base Information

Chemical Name:[(2R,3R,3aS,8bR)-2-(tert-Butyl-diphenyl-silanyloxy)-3-((E)-(S)-3-hydroxy-oct-1-enyl)-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-7-yl]-acetic acid methyl ester
CAS No.:131926-29-9
Molecular Formula:C₃₈H₄₈O₅Si
Molecular Weight:612.882
Hs Code.:

[(2R,3R,3aS,8bR)-2-(tert-Butyl-diphenyl-silanyloxy)-3-((E)-(S)-3-hydroxy-oct-1-enyl)-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-7-yl]-acetic acid methyl ester

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Chemical Property of [(2R,3R,3aS,8bR)-2-(tert-Butyl-diphenyl-silanyloxy)-3-((E)-(S)-3-hydroxy-oct-1-enyl)-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-7-yl]-acetic acid methyl ester

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Technology Process of [(2R,3R,3aS,8bR)-2-(tert-Butyl-diphenyl-silanyloxy)-3-((E)-(S)-3-hydroxy-oct-1-enyl)-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-7-yl]-acetic acid methyl ester

There total 44 articles about [(2R,3R,3aS,8bR)-2-(tert-Butyl-diphenyl-silanyloxy)-3-((E)-(S)-3-hydroxy-oct-1-enyl)-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-7-yl]-acetic 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:

: [(2R,3R,3aS,8bR)-2-(tert-Butyl-diphenyl-silanyloxy)-3-((E)-3-oxo-oct-1-enyl)-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-7-yl]-acetic acid methyl ester

: 131926-29-9,132016-43-4
[(2R,3R,3aS,8bR)-2-(tert-Butyl-diphenyl-silanyloxy)-3-((E)-(R)-3-hydroxy-oct-1-enyl)-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-7-yl]-acetic acid methyl ester

: 131926-29-9,132016-43-4
[(2R,3R,3aS,8bR)-2-(tert-Butyl-diphenyl-silanyloxy)-3-((E)-(S)-3-hydroxy-oct-1-enyl)-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-7-yl]-acetic acid methyl ester

Guidance literature:: With sodium tetrahydroborate; cerium(III) chloride; In tetrahydrofuran; methanol; at 0 ℃; for 0.0833333h; Yield given. Yields of byproduct given;
DOI:10.3987/COM-90-5371

Reference yield:

: [(2R,3R,3aS,8bR)-2-(tert-Butyl-diphenyl-silanyloxy)-3-((E)-3-oxo-oct-1-enyl)-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-7-yl]-acetic acid methyl ester

: 131926-29-9,132016-43-4
[(2R,3R,3aS,8bR)-2-(tert-Butyl-diphenyl-silanyloxy)-3-((E)-(R)-3-hydroxy-oct-1-enyl)-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-7-yl]-acetic acid methyl ester

: 131926-29-9,132016-43-4
[(2R,3R,3aS,8bR)-2-(tert-Butyl-diphenyl-silanyloxy)-3-((E)-(S)-3-hydroxy-oct-1-enyl)-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-7-yl]-acetic acid methyl ester

Guidance literature:: With sodium tetrahydroborate; cerium(III) chloride; In tetrahydrofuran; methanol; at 0 ℃; for 0.0833333h; Yield given. Yields of byproduct given;
DOI:10.3987/COM-90-5371

Reference yield:

: 14199-15-6
Methyl 4-hydroxyphenylacetate

: 131926-29-9,132016-43-4
[(2R,3R,3aS,8bR)-2-(tert-Butyl-diphenyl-silanyloxy)-3-((E)-(R)-3-hydroxy-oct-1-enyl)-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-7-yl]-acetic acid methyl ester

Guidance literature:: Multi-step reaction with 16 steps

1: 66 percent / NBS / dimethylformamide

2: PPTS / CH₂Cl₂

3: LiAlH₄ / diethyl ether

4: i-Pr₂NEt / CH₂Cl₂

6: 72 percent / PPTS / methanol

7: 95 percent / propylene oxide / CH₂Cl₂ / 0 - 20 °C

8: 60 percent / benzene / 5 h / Irradiation

9: 85 percent / TMSCl, NaI / acetonitrile / 0.83 h / -15 °C

11: diethyl ether

12: 1.) PhSeCl, 2.) Py, 30percent H₂O₂ / 1.) CCl₄, 0 deg C, 10 min, 2.) RT, 1 h

13: 86 percent / 18-Crown-6 / toluene / 19 h / Heating

14: 1.) OsO₄, Me₃NO, 2.) NaIO₄ / 1.) MeCOMe, THF, H₂O, RT, 4 h, 2.) DME, H₂O, RT, overnight

15: 1.) NaH / 1.) THF, RT, 20 min, 2.) RT, 40 min

16: CeCl₃*7H₂O, NaBH₄ / tetrahydrofuran; methanol / 0.08 h / 0 °C

With pyridine; sodium tetrahydroborate; sodium periodate; N-Bromosuccinimide; osmium(VIII) oxide; lithium aluminium tetrahydride; chloro-trimethyl-silane; Phenylselenyl chloride; cerium(III) chloride; 18-crown-6 ether; trimethylamine-N-oxide; dihydrogen peroxide; pyridinium p-toluenesulfonate; sodium hydride; N-ethyl-N,N-diisopropylamine; methyloxirane; sodium iodide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; benzene;
DOI:10.3987/COM-90-5371