(1S,4S)-1-(tert-Butyl-dimethyl-silanyloxy)-4-((S)-2,2-dibenzyl-[1,3]dioxolan-4-yl)-7-oxa-bicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylic acid dimethyl ester

Base Information

• Chemical Name: (1S,4S)-1-(tert-Butyl-dimethyl-silanyloxy)-4-((S)-2,2-dibenzyl-[1,3]dioxolan-4-yl)-7-oxa-bicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylic acid dimethyl ester
• CAS No.: 167611-79-2
• Molecular Formula: C₃₃H₄₀O₈Si
• Molecular Weight: 592.761

Synonyms:(1S,4S)-1-(tert-Butyl-dimethyl-silanyloxy)-4-((S)-2,2-dibenzyl-[1,3]dioxolan-4-yl)-7-oxa-bicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylic acid dimethyl ester

Chemical Property of (1S,4S)-1-(tert-Butyl-dimethyl-silanyloxy)-4-((S)-2,2-dibenzyl-[1,3]dioxolan-4-yl)-7-oxa-bicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylic acid dimethyl ester

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Technology Process of (1S,4S)-1-(tert-Butyl-dimethyl-silanyloxy)-4-((S)-2,2-dibenzyl-[1,3]dioxolan-4-yl)-7-oxa-bicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylic acid dimethyl ester

There total 1 articles about (1S,4S)-1-(tert-Butyl-dimethyl-silanyloxy)-4-((S)-2,2-dibenzyl-[1,3]dioxolan-4-yl)-7-oxa-bicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylic acid dimethyl 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:

5-((S)-2,2-Dibenzyl-[1,3]dioxolan-4-yl)-5H-furan-2-one + tert-Butyl-[5-((S)-2,2-dibenzyl-[1,3]dioxolan-4-yl)-furan-2-yloxy]-dimethyl-silane → (1S,4S)-1-(tert-Butyl-dimethyl-silanyloxy)-4-((S)-2,2-dibenzyl-[1,3]dioxolan-4-yl)-7-oxa-bicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylic acid dimethyl ester (167611-79-2) + (1R,4R)-1-(tert-Butyl-dimethyl-silanyloxy)-4-((S)-2,2-dibenzyl-[1,3]dioxolan-4-yl)-7-oxa-bicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylic acid dimethyl ester

Guidance literature:

With tris{3-(heptafluoropropylhydroxymethylene)-(+)-camphorato}europium(III); In neat (no solvent); for 22h; Yield given. Yields of byproduct given; Ambient temperature;

DOI:10.1016/0040-4039(95)00056-I

Reference yield: 82.0%

(1S,4S)-1-(tert-Butyl-dimethyl-silanyloxy)-4-((S)-2,2-dibenzyl-[1,3]dioxolan-4-yl)-7-oxa-bicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylic acid dimethyl ester (167611-79-2) → (1S,4S)-1-(tert-Butyl-dimethyl-silanyloxy)-4-((S)-2,2-dibenzyl-[1,3]dioxolan-4-yl)-7-oxa-bicyclo[2.2.1]hept-2-ene-2,3-dicarboxylic acid dimethyl ester

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate;

DOI:10.1016/0040-4039(95)00056-I

Reference yield:

(1S,4S)-1-(tert-Butyl-dimethyl-silanyloxy)-4-((S)-2,2-dibenzyl-[1,3]dioxolan-4-yl)-7-oxa-bicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylic acid dimethyl ester (167611-79-2) → (S)-3-((S)-2,2-Dibenzyl-[1,3]dioxolan-4-yl)-3-hydroxy-6-oxo-cyclohex-1-ene-1,2-dicarboxylic acid dimethyl ester

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / H₂ / 5percent Pd-C / ethyl acetate

2: 96 percent / tetrabutylammonium fluoride / tetrahydrofuran / -78 °C

With tetrabutyl ammonium fluoride; hydrogen; palladium on activated charcoal; In tetrahydrofuran; ethyl acetate;

DOI:10.1016/0040-4039(95)00056-I

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