Acetic acid (S)-[(1R,2S,4R,5S)-5-(tert-butyl-diphenyl-silanyloxy)-3,3-dimethyl-2-vinyl-7-oxa-bicyclo[2.2.1]hept-1-yl]-{4-[2-(tert-butyl-diphenyl-silanyloxymethyl)-cyclopropylmethyl]-2-vinyl-cyclohex-1-enyl}-methyl ester

Base Information

Chemical Name:Acetic acid (S)-[(1R,2S,4R,5S)-5-(tert-butyl-diphenyl-silanyloxy)-3,3-dimethyl-2-vinyl-7-oxa-bicyclo[2.2.1]hept-1-yl]-{4-[2-(tert-butyl-diphenyl-silanyloxymethyl)-cyclopropylmethyl]-2-vinyl-cyclohex-1-enyl}-methyl ester
CAS No.:471913-21-0
Molecular Formula:C₅₈H₇₄O₅Si₂
Molecular Weight:907.394
Hs Code.:

Acetic acid (S)-[(1R,2S,4R,5S)-5-(tert-butyl-diphenyl-silanyloxy)-3,3-dimethyl-2-vinyl-7-oxa-bicyclo[2.2.1]hept-1-yl]-{4-[2-(tert-butyl-diphenyl-silanyloxymethyl)-cyclopropylmethyl]-2-vinyl-cyclohex-1-enyl}-methyl ester

Synonyms:Acetic acid (S)-[(1R,2S,4R,5S)-5-(tert-butyl-diphenyl-silanyloxy)-3,3-dimethyl-2-vinyl-7-oxa-bicyclo[2.2.1]hept-1-yl]-{4-[2-(tert-butyl-diphenyl-silanyloxymethyl)-cyclopropylmethyl]-2-vinyl-cyclohex-1-enyl}-methyl ester

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Chemical Property of Acetic acid (S)-[(1R,2S,4R,5S)-5-(tert-butyl-diphenyl-silanyloxy)-3,3-dimethyl-2-vinyl-7-oxa-bicyclo[2.2.1]hept-1-yl]-{4-[2-(tert-butyl-diphenyl-silanyloxymethyl)-cyclopropylmethyl]-2-vinyl-cyclohex-1-enyl}-methyl ester

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Technology Process of Acetic acid (S)-[(1R,2S,4R,5S)-5-(tert-butyl-diphenyl-silanyloxy)-3,3-dimethyl-2-vinyl-7-oxa-bicyclo[2.2.1]hept-1-yl]-{4-[2-(tert-butyl-diphenyl-silanyloxymethyl)-cyclopropylmethyl]-2-vinyl-cyclohex-1-enyl}-methyl ester

There total 23 articles about Acetic acid (S)-[(1R,2S,4R,5S)-5-(tert-butyl-diphenyl-silanyloxy)-3,3-dimethyl-2-vinyl-7-oxa-bicyclo[2.2.1]hept-1-yl]-{4-[2-(tert-butyl-diphenyl-silanyloxymethyl)-cyclopropylmethyl]-2-vinyl-cyclohex-1-enyl}-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:

: (+/-)-(R,R)-[2-(tert-butyldiphenylsilyloxymethyl)cyclopropyl]methanol

: 471913-21-0
Acetic acid (S)-[(1R,2S,4R,5S)-5-(tert-butyl-diphenyl-silanyloxy)-3,3-dimethyl-2-vinyl-7-oxa-bicyclo[2.2.1]hept-1-yl]-{4-[2-(tert-butyl-diphenyl-silanyloxymethyl)-cyclopropylmethyl]-2-vinyl-cyclohex-1-enyl}-methyl ester

Guidance literature:: Multi-step reaction with 14 steps

1.1: PPh₃ / acetonitrile; toluene / 0.17 h / 0 °C

1.2: imidazole / acetonitrile; toluene / 0.25 h / 0 °C

1.3: 75 percent / I₂ / acetonitrile; toluene / 0.5 h / 0 °C

2.1: 84 percent / toluene / 16 h / 100 °C

3.1: t-BuOK / tetrahydrofuran; toluene / 0.5 h / 70 °C

3.2: 95 percent / tetrahydrofuran; toluene / 6 h / 70 °C

4.1: 98 percent / H₂ / PtO₂ / ethyl acetate / 0.67 h / 760 Torr

5.1: 76 percent / p-TsOH / acetone / 7 h / 40 °C

6.1: LDA / tetrahydrofuran / 1 h / -78 - 0 °C

6.2: 84 percent / HMPA / 0.17 h / -78 °C

7.1: NaH / tetrahydrofuran / 0.5 h / 0 °C

7.2: 95 percent / tetrahydrofuran / 1.5 h / 0 - 20 °C

8.1: 71 percent / CrCl₂ / NiCl₂ / dimethylformamide / 18 h / 50 °C

9.1: LiAlH₄ / diethyl ether / 0.5 h / 20 °C

10.1: imidazole / dimethylformamide

11.1: 94 percent / pyridine / CH₂Cl₂

12.1: 92 percent / CSA / methanol / 0 °C

13.1: 91 percent / NMO / TPAP / acetone

14.1: tetrahydrofuran / 0 °C

With pyridine; 1H-imidazole; chromium dichloride; lithium aluminium tetrahydride; N-methyl-2-indolinone; camphor-10-sulfonic acid; potassium tert-butylate; hydrogen; sodium hydride; toluene-4-sulfonic acid; triphenylphosphine; lithium diisopropyl amide; platinum(IV) oxide; tetrapropylammonium perruthennate; nickel dichloride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; 14.1: Wittig olefination;
DOI:10.1039/b202020n

Reference yield:

: 470690-19-8
(1R,2S,4S)-1-hydroxymethyl-3,3-dimethyl-7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylic acid ethyl ester

: 471913-21-0
Acetic acid (S)-[(1R,2S,4R,5S)-5-(tert-butyl-diphenyl-silanyloxy)-3,3-dimethyl-2-vinyl-7-oxa-bicyclo[2.2.1]hept-1-yl]-{4-[2-(tert-butyl-diphenyl-silanyloxymethyl)-cyclopropylmethyl]-2-vinyl-cyclohex-1-enyl}-methyl ester

Guidance literature:: Multi-step reaction with 15 steps

1.1: 91 percent / p-TsOH*H₂O / 16 h / 20 °C

2.1: disiamylborane / tetrahydrofuran / 16 h / -20 °C

2.2: 76 percent / aq. NaOH; H₂O₂ / tetrahydrofuran / 3 h

3.1: 89 percent / imidazole / CH₂Cl₂ / 16 h / 20 °C

4.1: 95 percent / LiAlH₄ / diethyl ether / 0.25 h / 20 °C

5.1: 88 percent / NMO / TPAP / acetone / 2 h

6.1: n-BuLi / tetrahydrofuran; hexane / 1 h / 0 °C

6.2: 89 percent / tetrahydrofuran / 2 h / 20 °C

7.1: 96 percent / aq. HOAc / tetrahydrofuran / 16 h / 60 °C

8.1: 83 percent / SO₃*pyridine; DMSO / CH₂Cl₂ / 3 h / 20 °C

9.1: 71 percent / CrCl₂ / NiCl₂ / dimethylformamide / 18 h / 50 °C

10.1: LiAlH₄ / diethyl ether / 0.5 h / 20 °C

11.1: imidazole / dimethylformamide

12.1: 94 percent / pyridine / CH₂Cl₂

13.1: 92 percent / CSA / methanol / 0 °C

14.1: 91 percent / NMO / TPAP / acetone

15.1: tetrahydrofuran / 0 °C

With pyridine; 1H-imidazole; chromium dichloride; lithium aluminium tetrahydride; n-butyllithium; N-methyl-2-indolinone; pyridine-SO₃ complex; camphor-10-sulfonic acid; bis-(1,2-dimethylpropyl)borane; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; tetrapropylammonium perruthennate; nickel dichloride; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; 6.2: Wittig olefination / 15.1: Wittig olefination;
DOI:10.1039/b202020n

Reference yield:

: 471269-86-0
(1R,2S,4R,5S)-5-hydroxy-3,3-dimethyl-1-[(2R*)-tetrahydropyran-2-yloxymethyl]-7-oxabicyclo[2.2.1]heptane-2-carboxylic acid ethyl ester

: 471913-21-0
Acetic acid (S)-[(1R,2S,4R,5S)-5-(tert-butyl-diphenyl-silanyloxy)-3,3-dimethyl-2-vinyl-7-oxa-bicyclo[2.2.1]hept-1-yl]-{4-[2-(tert-butyl-diphenyl-silanyloxymethyl)-cyclopropylmethyl]-2-vinyl-cyclohex-1-enyl}-methyl ester

Guidance literature:: Multi-step reaction with 13 steps

1.1: 89 percent / imidazole / CH₂Cl₂ / 16 h / 20 °C

2.1: 95 percent / LiAlH₄ / diethyl ether / 0.25 h / 20 °C

3.1: 88 percent / NMO / TPAP / acetone / 2 h

4.1: n-BuLi / tetrahydrofuran; hexane / 1 h / 0 °C

4.2: 89 percent / tetrahydrofuran / 2 h / 20 °C

5.1: 96 percent / aq. HOAc / tetrahydrofuran / 16 h / 60 °C

6.1: 83 percent / SO₃*pyridine; DMSO / CH₂Cl₂ / 3 h / 20 °C

7.1: 71 percent / CrCl₂ / NiCl₂ / dimethylformamide / 18 h / 50 °C

8.1: LiAlH₄ / diethyl ether / 0.5 h / 20 °C

9.1: imidazole / dimethylformamide

10.1: 94 percent / pyridine / CH₂Cl₂

11.1: 92 percent / CSA / methanol / 0 °C

12.1: 91 percent / NMO / TPAP / acetone

13.1: tetrahydrofuran / 0 °C

With pyridine; 1H-imidazole; chromium dichloride; lithium aluminium tetrahydride; n-butyllithium; N-methyl-2-indolinone; pyridine-SO₃ complex; camphor-10-sulfonic acid; acetic acid; dimethyl sulfoxide; tetrapropylammonium perruthennate; nickel dichloride; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; 4.2: Wittig olefination / 13.1: Wittig olefination;
DOI:10.1039/b202020n