2-[(1S,2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-(6-methoxycarbonyl-hexyl)-cyclopentyl]-2-methyl-malonic acid dibenzyl ester

Base Information

Chemical Name:2-[(1S,2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-(6-methoxycarbonyl-hexyl)-cyclopentyl]-2-methyl-malonic acid dibenzyl ester
CAS No.:207991-42-2
Molecular Formula:C₃₇H₅₄O₇Si
Molecular Weight:638.917
Hs Code.:

Synonyms:2-[(1S,2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-(6-methoxycarbonyl-hexyl)-cyclopentyl]-2-methyl-malonic acid dibenzyl ester

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Chemical Property of 2-[(1S,2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-(6-methoxycarbonyl-hexyl)-cyclopentyl]-2-methyl-malonic acid dibenzyl ester

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Technology Process of 2-[(1S,2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-(6-methoxycarbonyl-hexyl)-cyclopentyl]-2-methyl-malonic acid dibenzyl ester

There total 4 articles about 2-[(1S,2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-(6-methoxycarbonyl-hexyl)-cyclopentyl]-2-methyl-malonic acid dibenzyl 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: 96.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 207991-41-1
2-[(1S,2R,3S)-3-Hydroxy-2-(6-methoxycarbonyl-hexyl)-cyclopentyl]-2-methyl-malonic acid dibenzyl ester

: 207991-42-2
2-[(1S,2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-(6-methoxycarbonyl-hexyl)-cyclopentyl]-2-methyl-malonic acid dibenzyl ester

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at -78 ℃; for 0.5h;
DOI:10.1021/jo9723319

Reference yield:

: 2-[(1S,2S)-2-(1-Hydroxy-6-methoxycarbonyl-hexyl)-3-oxo-cyclopentyl]-2-methyl-malonic acid dibenzyl ester

: 207991-42-2
2-[(1S,2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-(6-methoxycarbonyl-hexyl)-cyclopentyl]-2-methyl-malonic acid dibenzyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 53 percent / DMAP / acetonitrile

2: 46 percent / Bu₃SnH, (t-BuO)2 / 50 °C

3: 88 percent / L-Selectride / CH₂Cl₂; tetrahydrofuran / 1 h / -78 °C

4: 96 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C

With 2,6-dimethylpyridine; dmap; di-tert-butyl peroxide; tri-n-butyl-tin hydride; L-Selectride; In tetrahydrofuran; dichloromethane; acetonitrile;
DOI:10.1021/jo9723319

Reference yield:

: 207991-40-0
2-[(1S,2R)-2-(6-Methoxycarbonyl-hexyl)-3-oxo-cyclopentyl]-2-methyl-malonic acid dibenzyl ester

: 207991-42-2
2-[(1S,2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-(6-methoxycarbonyl-hexyl)-cyclopentyl]-2-methyl-malonic acid dibenzyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 88 percent / L-Selectride / CH₂Cl₂; tetrahydrofuran / 1 h / -78 °C

2: 96 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C

With 2,6-dimethylpyridine; L-Selectride; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo9723319