(2S)-2-(tert-butyldiphenylsilanyloxy)propionic acid (3S)-3-hydroxy-4-methanesulfonyloxy-3-methylbutyl ester

Base Information

Chemical Name:(2S)-2-(tert-butyldiphenylsilanyloxy)propionic acid (3S)-3-hydroxy-4-methanesulfonyloxy-3-methylbutyl ester
CAS No.:199921-28-3
Molecular Formula:C₂₅H₃₆O₇SSi
Molecular Weight:508.708
Hs Code.:

Synonyms:(2S)-2-(tert-butyldiphenylsilanyloxy)propionic acid (3S)-3-hydroxy-4-methanesulfonyloxy-3-methylbutyl ester

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Chemical Property of (2S)-2-(tert-butyldiphenylsilanyloxy)propionic acid (3S)-3-hydroxy-4-methanesulfonyloxy-3-methylbutyl ester

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Technology Process of (2S)-2-(tert-butyldiphenylsilanyloxy)propionic acid (3S)-3-hydroxy-4-methanesulfonyloxy-3-methylbutyl ester

There total 3 articles about (2S)-2-(tert-butyldiphenylsilanyloxy)propionic acid (3S)-3-hydroxy-4-methanesulfonyloxy-3-methylbutyl 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: 98.0%

: 124-63-0
methanesulfonyl chloride

: 199921-27-2
(2S)-2-(tert-butyldiphenylsilanyloxy)propionic acid (3S)-3,4-dihydroxy-3-methylbutyl ester

: 199921-28-3
(2S)-2-(tert-butyldiphenylsilanyloxy)propionic acid (3S)-3-hydroxy-4-methanesulfonyloxy-3-methylbutyl ester

Guidance literature:: With triethylamine; In dichloromethane; at -10 ℃; for 0.25h;
DOI:10.1016/S0040-4020(97)01038-7

Reference yield:

: 64018-43-5
2-[(4S)-2,2,4-trimethyl-1,3-dioxolan-4-yl]ethanol

: 199921-28-3
(2S)-2-(tert-butyldiphenylsilanyloxy)propionic acid (3S)-3-hydroxy-4-methanesulfonyloxy-3-methylbutyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 69 percent / 4-dimethylaminopyridine; 4-dimethylaminopyridine hydrochloride; 1,3-dicyclohexylcarbodiimide / CH₂Cl₂ / 20.5 h / 22 °C

2: 52 percent / aq. H₂SO₄ / tetrahydrofuran / 4 h / 50 °C

3: 98 percent / triethylamine / CH₂Cl₂ / 0.25 h / -10 °C

With dmap; sulfuric acid; 4-(dimethylamino)pyridine hydrochloride; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; 1: Esterification / 2: Ring cleavage / 3: sulfonylation;
DOI:10.1016/S0040-4020(97)01038-7

Reference yield:

: 199921-26-1
(2S)-2-(tert-butyldiphenylsilanyloxy)propionic acid 2-[(4S)-2,2,4-trimethyl-1,3-dioxolan-4-yl]ethyl ester

: 199921-28-3
(2S)-2-(tert-butyldiphenylsilanyloxy)propionic acid (3S)-3-hydroxy-4-methanesulfonyloxy-3-methylbutyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 52 percent / aq. H₂SO₄ / tetrahydrofuran / 4 h / 50 °C

2: 98 percent / triethylamine / CH₂Cl₂ / 0.25 h / -10 °C

With sulfuric acid; triethylamine; In tetrahydrofuran; dichloromethane; 1: Ring cleavage / 2: sulfonylation;
DOI:10.1016/S0040-4020(97)01038-7