(1R,3R,3aS,5R,7aR)-5-(tert-Butyl-diphenyl-silanyloxy)-3-(2-hydroxy-2-methyl-but-3-enyl)-1,3,3a,4,5,7a-hexahydro-isobenzofuran-1-carboxylic acid methyl ester

Base Information

Chemical Name:(1R,3R,3aS,5R,7aR)-5-(tert-Butyl-diphenyl-silanyloxy)-3-(2-hydroxy-2-methyl-but-3-enyl)-1,3,3a,4,5,7a-hexahydro-isobenzofuran-1-carboxylic acid methyl ester
CAS No.:369361-84-2
Molecular Formula:C₃₁H₄₀O₅Si
Molecular Weight:520.741
Hs Code.:

(1R,3R,3aS,5R,7aR)-5-(tert-Butyl-diphenyl-silanyloxy)-3-(2-hydroxy-2-methyl-but-3-enyl)-1,3,3a,4,5,7a-hexahydro-isobenzofuran-1-carboxylic acid methyl ester

Synonyms:(1R,3R,3aS,5R,7aR)-5-(tert-Butyl-diphenyl-silanyloxy)-3-(2-hydroxy-2-methyl-but-3-enyl)-1,3,3a,4,5,7a-hexahydro-isobenzofuran-1-carboxylic acid methyl ester

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Chemical Property of (1R,3R,3aS,5R,7aR)-5-(tert-Butyl-diphenyl-silanyloxy)-3-(2-hydroxy-2-methyl-but-3-enyl)-1,3,3a,4,5,7a-hexahydro-isobenzofuran-1-carboxylic acid methyl ester

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Technology Process of (1R,3R,3aS,5R,7aR)-5-(tert-Butyl-diphenyl-silanyloxy)-3-(2-hydroxy-2-methyl-but-3-enyl)-1,3,3a,4,5,7a-hexahydro-isobenzofuran-1-carboxylic acid methyl ester

There total 11 articles about (1R,3R,3aS,5R,7aR)-5-(tert-Butyl-diphenyl-silanyloxy)-3-(2-hydroxy-2-methyl-but-3-enyl)-1,3,3a,4,5,7a-hexahydro-isobenzofuran-1-carboxylic 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: 91.0%

: 124-41-4
sodium methylate

: 287934-67-2
(1R,3R,3aS,5R,7aR)-5-(tert-Butyl-diphenyl-silanyloxy)-3-(2-hydroxy-2-methyl-but-3-enyl)-1,3,3a,4,5,7a-hexahydro-isobenzofuran-1-carbonitrile

: 369361-84-2
(1R,3R,3aS,5R,7aR)-5-(tert-Butyl-diphenyl-silanyloxy)-3-(2-hydroxy-2-methyl-but-3-enyl)-1,3,3a,4,5,7a-hexahydro-isobenzofuran-1-carboxylic acid methyl ester

Guidance literature:: With oxonium; In methanol;
DOI:10.1021/ja011285y

Reference yield:

: 198191-73-0
5-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-3a,4,5,7a-tetrahydro-3H-isobenzofuran-1-one

: 369361-84-2
(1R,3R,3aS,5R,7aR)-5-(tert-Butyl-diphenyl-silanyloxy)-3-(2-hydroxy-2-methyl-but-3-enyl)-1,3,3a,4,5,7a-hexahydro-isobenzofuran-1-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: aq. Bu₄NBr / tetrahydrofuran

2: Dibal-H / CH₂Cl₂ / -78 °C

3: Et₃N / CH₂Cl₂ / -78 - 20 °C

4: BF₃*OEt₂ / CH₂Cl₂ / -78 - 20 °C

5: 86 percent / O₂; PdCl₂; aq. CuCl / dimethylformamide

6: 87 percent / CeCl₃ / tetrahydrofuran

7: 91 percent / H₃O⁺ / methanol

With cerium(III) chloride; boron trifluoride diethyl etherate; oxonium; tetrabutylammomium bromide; oxygen; diisobutylaluminium hydride; triethylamine; copper(l) chloride; palladium dichloride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 5: Wacker oxidation;
DOI:10.1021/ja011285y

Reference yield:

: 198191-76-3
(3R,3aS,5R,7aR)-3-Allyl-5-(tert-butyl-diphenyl-silanyloxy)-3a,4,5,7a-tetrahydro-3H-isobenzofuran-1-one

: 369361-84-2
(1R,3R,3aS,5R,7aR)-5-(tert-Butyl-diphenyl-silanyloxy)-3-(2-hydroxy-2-methyl-but-3-enyl)-1,3,3a,4,5,7a-hexahydro-isobenzofuran-1-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: Dibal-H / CH₂Cl₂ / -78 °C

2: Et₃N / CH₂Cl₂ / -78 - 20 °C

3: BF₃*OEt₂ / CH₂Cl₂ / -78 - 20 °C

4: 86 percent / O₂; PdCl₂; aq. CuCl / dimethylformamide

5: 87 percent / CeCl₃ / tetrahydrofuran

6: 91 percent / H₃O⁺ / methanol

With cerium(III) chloride; boron trifluoride diethyl etherate; oxonium; oxygen; diisobutylaluminium hydride; triethylamine; copper(l) chloride; palladium dichloride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 4: Wacker oxidation;
DOI:10.1021/ja011285y