(4S,1'R)-4-(1'-benzyloxy-2'-hydroxyethyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

Base Information

Chemical Name:(4S,1'R)-4-(1'-benzyloxy-2'-hydroxyethyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester
CAS No.:437609-54-6
Molecular Formula:C₁₉H₂₉NO₅
Molecular Weight:351.443
Hs Code.:

Synonyms:(4S,1'R)-4-(1'-benzyloxy-2'-hydroxyethyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (4S,1'R)-4-(1'-benzyloxy-2'-hydroxyethyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

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Technology Process of (4S,1'R)-4-(1'-benzyloxy-2'-hydroxyethyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

There total 8 articles about (4S,1'R)-4-(1'-benzyloxy-2'-hydroxyethyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl 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%

: 437609-45-5
(4S,1'R)-4-(1'-benzyloxy-2'-tert-butyldimethylsilanyloxyethyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

: 437609-54-6
(4S,1'R)-4-(1'-benzyloxy-2'-hydroxyethyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 - 20 ℃; for 12h;
DOI:10.1021/ol0200448

Reference yield:

: 100-39-0
benzyl bromide

: 437609-54-6
(4S,1'R)-4-(1'-benzyloxy-2'-hydroxyethyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 95 percent / sodium hydride / dimethylformamide / 18 h / -5 - 20 °C

2: 91 percent / tetrabutylammonium fluoride / tetrahydrofuran / 12 h / 0 - 20 °C

With tetrabutyl ammonium fluoride; sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1021/ol0200448

Reference yield:

: 244023-85-6
(S)-3-(tert-butoxycarbonylamino)-1,5-dioxaspiro[3.2]hexane

: 437609-54-6
(4S,1'R)-4-(1'-benzyloxy-2'-hydroxyethyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 96 percent / CH₂Cl₂ / -78 - 20 °C

2: 88 percent / 10-camphorsulfonic acid / CH₂Cl₂ / 96 h / 20 °C

3: 31 percent / DIBAL / CH₂Cl₂ / 3 h / -78 °C

4: 94 percent / 4-(dimethylamino)pyridine; triethylamine / CH₂Cl₂ / 0 - 20 °C

5: 95 percent / sodium hydride / dimethylformamide / 18 h / -5 - 20 °C

6: 91 percent / tetrabutylammonium fluoride / tetrahydrofuran / 12 h / 0 - 20 °C

With dmap; (1S)-10-camphorsulfonic acid; tetrabutyl ammonium fluoride; sodium hydride; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ol0200448