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

Base Information

Chemical Name:(4S,1'R)-4-(1'-benzyloxy-2'-tert-butyldimethylsilanyloxyethyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester
CAS No.:437609-45-5
Molecular Formula:C₂₅H₄₃NO₅Si
Molecular Weight:465.706
Hs Code.:

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

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

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

There total 6 articles about (4S,1'R)-4-(1'-benzyloxy-2'-tert-butyldimethylsilanyloxyethyl)-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: 95.0%

: 100-39-0
benzyl bromide

: 437609-51-3
(4S,1'R)-4-(2'-tert-butyldimethylsilanyloxy-1'-hydroxyethyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

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

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; at -5 - 20 ℃; for 18h;
DOI:10.1021/ol0200448

Reference yield:

: 213338-89-7
(S)-3-(tert-butoxycarbonylamino)-2-methyleneoxetane

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

Guidance literature:: Multi-step reaction with 6 steps

1: 100 percent / dimethyldioxirane / CH₂Cl₂ / 1 h / -78 °C

2: 96 percent / CH₂Cl₂ / -78 - 20 °C

3: 88 percent / 10-camphorsulfonic acid / CH₂Cl₂ / 96 h / 20 °C

4: 31 percent / DIBAL / CH₂Cl₂ / 3 h / -78 °C

5: 94 percent / 4-(dimethylamino)pyridine; triethylamine / CH₂Cl₂ / 0 - 20 °C

6: 95 percent / sodium hydride / dimethylformamide / 18 h / -5 - 20 °C

With dmap; (1S)-10-camphorsulfonic acid; 3,3-dimethyldioxirane; sodium hydride; diisobutylaluminium hydride; triethylamine; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ol0200448

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 5 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

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