[(2R,3R,3aS,8bR)-2-(tert-Butyl-diphenyl-silanyloxy)-3-formyl-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-formyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-7-yl]-acetic acid methyl ester
CAS No.:131926-28-8
Molecular Formula:C₃₁H₃₄O₅Si
Molecular Weight:514.693
Hs Code.:

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

There total 20 articles about [(2R,3R,3aS,8bR)-2-(tert-Butyl-diphenyl-silanyloxy)-3-formyl-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:

: 14199-15-6
Methyl 4-hydroxyphenylacetate

: 131926-28-8
[(2R,3R,3aS,8bR)-2-(tert-Butyl-diphenyl-silanyloxy)-3-formyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-7-yl]-acetic acid methyl ester

Guidance literature:: Multi-step reaction with 14 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

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

Reference yield:

: 34918-57-5
methyl 3-bromo-4-hydroxyphenylacetate

: 131926-28-8
[(2R,3R,3aS,8bR)-2-(tert-Butyl-diphenyl-silanyloxy)-3-formyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-7-yl]-acetic acid methyl ester

Guidance literature:: Multi-step reaction with 13 steps

1: PPTS / CH₂Cl₂

2: LiAlH₄ / diethyl ether

3: i-Pr₂NEt / CH₂Cl₂

5: 72 percent / PPTS / methanol

6: 95 percent / propylene oxide / CH₂Cl₂ / 0 - 20 °C

7: 60 percent / benzene / 5 h / Irradiation

8: 85 percent / TMSCl, NaI / acetonitrile / 0.83 h / -15 °C

10: diethyl ether

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

12: 86 percent / 18-Crown-6 / toluene / 19 h / Heating

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

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

Reference yield:

: 85548-62-5
(1S,2S)-2-Phenylsulfanyl-cyclopent-3-enol

: 131926-28-8
[(2R,3R,3aS,8bR)-2-(tert-Butyl-diphenyl-silanyloxy)-3-formyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-7-yl]-acetic acid methyl ester

Guidance literature:: Multi-step reaction with 14 steps

1: various solvent(s); dimethylformamide

2: mCPBA / CH₂Cl₂ / -70 °C

3: PPh₃ / methanol; toluene / 65 °C

4: 1.) n-BuLi / 1.) HMPA, THF, -20 deg C

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

With pyridine; sodium periodate; osmium(VIII) oxide; n-butyllithium; chloro-trimethyl-silane; Phenylselenyl chloride; 18-crown-6 ether; trimethylamine-N-oxide; dihydrogen peroxide; pyridinium p-toluenesulfonate; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; methyloxirane; sodium iodide; In methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; benzene;
DOI:10.3987/COM-90-5371