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

Base Information

Chemical Name:(2R,4R,1'S)-2-(1'-benzyloxy-4'-hydroxyheptyl)-4-phenyloxazolidine-3-carboxylic acid tert-butyl ester
CAS No.:211861-30-2
Molecular Formula:C₂₈H₃₉NO₅
Molecular Weight:469.621
Hs Code.:

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

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

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

There total 5 articles about (2R,4R,1'S)-2-(1'-benzyloxy-4'-hydroxyheptyl)-4-phenyloxazolidine-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: 77.0%

: 927-77-5
n-propylmagnesium bromide

: 211861-29-9
(2R,4R,1'S)-2-(1'-benzyloxy-4'-oxobutyl)-4-phenyloxazolidine-3-carboxylic acid tert-butyl ester

: 211861-30-2
(2R,4R,1'S)-2-(1'-benzyloxy-4'-hydroxyheptyl)-4-phenyloxazolidine-3-carboxylic acid tert-butyl ester

Guidance literature:: In diethyl ether; at 0 ℃; for 0.5h;
DOI:10.1016/S0040-4020(98)00508-0

Reference yield:

: 164530-42-1
(2R,4R)-2-carboxy-4-phenyl-3-tert-butoxycarbonyloxazolidine

: 211861-30-2
(2R,4R,1'S)-2-(1'-benzyloxy-4'-hydroxyheptyl)-4-phenyloxazolidine-3-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) N-methylmorpholine, isobutyl chloroformate, 2.) triethylamine / 1.) THF, -20 deg C, 0.5 h, 2.) THF, DMF, 0 deg C, 2 h

2: 6.3 g / diethyl ether / 0.5 h / 0 °C

3: 2.6 g / CeCl₃(H₂O)7, sodium borohydride / ethanol / 0.5 h / -78 °C

4: 88 percent / sodium hydride / dimethylformamide / 2 h / Ambient temperature

5: 1.) OsO₄, 2.) NaIO₄ / 1.) THF, water, room temperature, 10 min, 2.) room temperature, 0.5 h

6: 77 percent / diethyl ether / 0.5 h / 0 °C

With 4-methyl-morpholine; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; cerium(III) chloride; sodium hydride; triethylamine; isobutyl chloroformate; In diethyl ether; ethanol; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(98)00508-0

Reference yield:

: 164530-43-2
Weinreb amide

: 211861-30-2
(2R,4R,1'S)-2-(1'-benzyloxy-4'-hydroxyheptyl)-4-phenyloxazolidine-3-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 6.3 g / diethyl ether / 0.5 h / 0 °C

2: 2.6 g / CeCl₃(H₂O)7, sodium borohydride / ethanol / 0.5 h / -78 °C

3: 88 percent / sodium hydride / dimethylformamide / 2 h / Ambient temperature

4: 1.) OsO₄, 2.) NaIO₄ / 1.) THF, water, room temperature, 10 min, 2.) room temperature, 0.5 h

5: 77 percent / diethyl ether / 0.5 h / 0 °C

With sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; cerium(III) chloride; sodium hydride; In diethyl ether; ethanol; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(98)00508-0