(4S,5R)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-5-thiazol-2-yl-oxazolidine-3-carboxylic acid tert-butyl ester

Base Information

Chemical Name:(4S,5R)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-5-thiazol-2-yl-oxazolidine-3-carboxylic acid tert-butyl ester
CAS No.:138319-96-7
Molecular Formula:C₃₀H₄₀N₂O₄SSi
Molecular Weight:552.81
Hs Code.:

Synonyms:(4S,5R)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-5-thiazol-2-yl-oxazolidine-3-carboxylic acid tert-butyl ester

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Chemical Property of (4S,5R)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-5-thiazol-2-yl-oxazolidine-3-carboxylic acid tert-butyl ester

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Technology Process of (4S,5R)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-5-thiazol-2-yl-oxazolidine-3-carboxylic acid tert-butyl ester

There total 11 articles about (4S,5R)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-5-thiazol-2-yl-oxazolidine-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: 90.0%

: 138319-92-3
[(1S,2R)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-2-hydroxy-2-thiazol-2-yl-ethyl]-carbamic acid tert-butyl ester

: 77-76-9
2,2-dimethoxy-propane

: 138319-96-7
(4S,5R)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-5-thiazol-2-yl-oxazolidine-3-carboxylic acid tert-butyl ester

Guidance literature:: With toluene-4-sulfonic acid; In benzene; for 24h; Heating;
DOI:10.1039/c39910001576

Reference yield: 89.0%

: 138319-92-3
(1S,2R)-2-<(tert-Butoxycarbonyl)amino>-3-<(tert-butyldiphenylsilyl)oxy>-1-(1,3-thiazol-2-yl)-1-propanol

: 77-76-9
2,2-dimethoxy-propane

: 138319-96-7
(1S,2R)-2-<(tert-Butoxycarbonyl)amino>-3-<(tert-butyldiphenylsilyl)oxy>-1-hydroxy-2-N,1-O-isopropylidene-1-(1,3-thiazol-2-yl)propane

Guidance literature:: With camphor-10-sulfonic acid; In toluene; for 2h; Heating;
DOI:10.1021/jo00120a017

Reference yield:

: 108149-60-6,95715-86-9
methyl [(4R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidin-4-yl]carboxylate

: 138319-96-7
(1S,2R)-2-<(tert-Butoxycarbonyl)amino>-3-<(tert-butyldiphenylsilyl)oxy>-1-hydroxy-2-N,1-O-isopropylidene-1-(1,3-thiazol-2-yl)propane

Guidance literature:: Multi-step reaction with 5 steps

1: n-BuLi / 1.) Et₂O, hexane, -70 deg C, 20 min, 2.) -65 deg C, 3 h

2: NaBH₄ / methanol / 1.) -55 deg C, 2 h, 2.) -55 to 0 deg C

3: PPTS, MeOH / 18 h / 60 °C

4: Et₃N, DMAP / dimethylformamide / 5 h / Ambient temperature

5: 89 percent / CSA / toluene / 2 h / Heating

With methanol; dmap; sodium tetrahydroborate; n-butyllithium; camphor-10-sulfonic acid; pyridinium p-toluenesulfonate; triethylamine; In methanol; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo00120a017