3-[5-(tert-butyl-diphenyl-silanyloxy)-3,3-dimethyl-2-vinyl-7-oxa-bicyclo[2.2.1]hept-1-yl]-6-[2-(tert-butyl-diphenyl-silanyloxymethyl)-cyclopropylmethyl]-4,5,6,7-tetrahydro-3H-isobenzofuran-1-one

Base Information

• Chemical Name: 3-[5-(tert-butyl-diphenyl-silanyloxy)-3,3-dimethyl-2-vinyl-7-oxa-bicyclo[2.2.1]hept-1-yl]-6-[2-(tert-butyl-diphenyl-silanyloxymethyl)-cyclopropylmethyl]-4,5,6,7-tetrahydro-3H-isobenzofuran-1-one
• CAS No.: 471913-15-2
• Molecular Formula: C₅₅H₆₈O₅Si₂
• Molecular Weight: 865.313

Synonyms:3-[5-(tert-butyl-diphenyl-silanyloxy)-3,3-dimethyl-2-vinyl-7-oxa-bicyclo[2.2.1]hept-1-yl]-6-[2-(tert-butyl-diphenyl-silanyloxymethyl)-cyclopropylmethyl]-4,5,6,7-tetrahydro-3H-isobenzofuran-1-one

Chemical Property of 3-[5-(tert-butyl-diphenyl-silanyloxy)-3,3-dimethyl-2-vinyl-7-oxa-bicyclo[2.2.1]hept-1-yl]-6-[2-(tert-butyl-diphenyl-silanyloxymethyl)-cyclopropylmethyl]-4,5,6,7-tetrahydro-3H-isobenzofuran-1-one

Chemical Property:

Purity/Quality:

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Technology Process of 3-[5-(tert-butyl-diphenyl-silanyloxy)-3,3-dimethyl-2-vinyl-7-oxa-bicyclo[2.2.1]hept-1-yl]-6-[2-(tert-butyl-diphenyl-silanyloxymethyl)-cyclopropylmethyl]-4,5,6,7-tetrahydro-3H-isobenzofuran-1-one

There total 16 articles about 3-[5-(tert-butyl-diphenyl-silanyloxy)-3,3-dimethyl-2-vinyl-7-oxa-bicyclo[2.2.1]hept-1-yl]-6-[2-(tert-butyl-diphenyl-silanyloxymethyl)-cyclopropylmethyl]-4,5,6,7-tetrahydro-3H-isobenzofuran-1-one 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: 71.0%

(+)-(1R,2S,4R,5S)-5-(tert-butyldiphenylsilyloxy)-3,3-dimethyl-2-vinyl-7-oxabicyclo[2.2.1]heptancarboxaldehyde (301823-94-9) + (+/-)-5-[2-(tert-butyldiphenylsilyloxymethyl)-(R,R)-cyclopropylmethyl]-2-trifluoromethylsulfonyloxycyclohex-1-enecarboxylic acid ethyl ester → 3-[5-(tert-butyl-diphenyl-silanyloxy)-3,3-dimethyl-2-vinyl-7-oxa-bicyclo[2.2.1]hept-1-yl]-6-[2-(tert-butyl-diphenyl-silanyloxymethyl)-cyclopropylmethyl]-4,5,6,7-tetrahydro-3H-isobenzofuran-1-one + 3-[5-(tert-butyl-diphenyl-silanyloxy)-3,3-dimethyl-2-vinyl-7-oxa-bicyclo[2.2.1]hept-1-yl]-6-[2-(tert-butyl-diphenyl-silanyloxymethyl)-cyclopropylmethyl]-4,5,6,7-tetrahydro-3H-isobenzofuran-1-one (471913-15-2)

Guidance literature:

With chromium dichloride; nickel dichloride; In N,N-dimethyl-formamide; at 50 ℃; for 18h;

DOI:10.1039/b202020n

Reference yield:

(+/-)-(R,R)-[2-(tert-butyldiphenylsilyloxymethyl)cyclopropyl]methanol → 3-[5-(tert-butyl-diphenyl-silanyloxy)-3,3-dimethyl-2-vinyl-7-oxa-bicyclo[2.2.1]hept-1-yl]-6-[2-(tert-butyl-diphenyl-silanyloxymethyl)-cyclopropylmethyl]-4,5,6,7-tetrahydro-3H-isobenzofuran-1-one (471913-15-2)

Guidance literature:

Multi-step reaction with 8 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

With chromium dichloride; potassium tert-butylate; hydrogen; sodium hydride; toluene-4-sulfonic acid; triphenylphosphine; lithium diisopropyl amide; platinum(IV) oxide; nickel dichloride; In tetrahydrofuran; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; acetonitrile;

DOI:10.1039/b202020n

Reference yield:

(1R,2S,4S)-1-hydroxymethyl-3,3-dimethyl-7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylic acid ethyl ester (470690-19-8) → 3-[5-(tert-butyl-diphenyl-silanyloxy)-3,3-dimethyl-2-vinyl-7-oxa-bicyclo[2.2.1]hept-1-yl]-6-[2-(tert-butyl-diphenyl-silanyloxymethyl)-cyclopropylmethyl]-4,5,6,7-tetrahydro-3H-isobenzofuran-1-one (471913-15-2)

Guidance literature:

Multi-step reaction with 9 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

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

DOI:10.1039/b202020n

upstream raw materials:

(+)-(1R,2S,4R,5S)-5-(tert-butyldiphenylsilyloxy)-3,3-dimethyl-2-vinyl-7-oxabicyclo[2.2.1]heptancarboxaldehyde

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

(1R,2S,4S)-3,3-dimethyl-1-[(2R*)-tetrahydropyran-2-yloxymethyl]-7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylic acid ethyl ester

(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

Downstream raw materials:

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

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

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-hydroxymethyl-cyclohex-1-enyl}-methyl ester

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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