(4S,5R)-4-Cyclohexylmethyl-5-((R)-hydroxy-thiazol-2-yl-methyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (4S,5R)-4-Cyclohexylmethyl-5-((R)-hydroxy-thiazol-2-yl-methyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
• CAS No.: 126223-10-7
• Molecular Formula: C₂₁H₃₄N₂O₄S
• Molecular Weight: 410.578
• Mol file: 126223-10-7.mol

Synonyms:

Chemical Property of (4S,5R)-4-Cyclohexylmethyl-5-((R)-hydroxy-thiazol-2-yl-methyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5R)-4-Cyclohexylmethyl-5-((R)-hydroxy-thiazol-2-yl-methyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

There total 3 articles about (4S,5R)-4-Cyclohexylmethyl-5-((R)-hydroxy-thiazol-2-yl-methyl)-2,2-dimethyl-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:

((S)-1-Cyclohexylmethyl-2-hydroxy-2-thiazol-2-yl-ethyl)-carbamic acid tert-butyl ester → (4S,5R)-4-Cyclohexylmethyl-5-((R)-hydroxy-thiazol-2-yl-methyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (126223-10-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 62 percent / 4-toluenesulfonic acid

3: 2.) (n-BU)4NF*3H₂O / 1.) CH₂Cl₂, -40 deg C to room temperature, 2.) THF, 2 h

With tetrabutyl ammonium fluoride; toluene-4-sulfonic acid;

DOI:10.1016/S0040-4039(00)61634-9

Reference yield:

2-<(4S,5R)-3-tert-butoxycarbonyl-4-cyclohexylmethyl-2,2-dimethyl-1,3-oxazolidin-5-yl>-1,3-thiazole (143131-18-4) → (4S,5R)-4-Cyclohexylmethyl-5-((R)-hydroxy-thiazol-2-yl-methyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (126223-10-7)

Guidance literature:

Multi-step reaction with 2 steps

2: 2.) (n-BU)4NF*3H₂O / 1.) CH₂Cl₂, -40 deg C to room temperature, 2.) THF, 2 h

With tetrabutyl ammonium fluoride;

DOI:10.1016/S0040-4039(00)61634-9

Reference yield:

2-(trimethylsilyl)thiazole (79265-30-8) + tert-butyl (4S,5R)-4-(cyclohexylmethyl)-5-formyl-2,2-dimethyl-3-oxazolidinecarboxylate (117997-58-7) → (4S,5R)-4-Cyclohexylmethyl-5-((R)-hydroxy-thiazol-2-yl-methyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (126223-10-7)

Guidance literature:

With tetrabutyl ammonium fluoride; Yield given. Multistep reaction; 1.) CH₂Cl₂, -40 deg C to room temperature, 2.) THF, 2 h;

DOI:10.1016/S0040-4039(00)61634-9

upstream raw materials:

2-(trimethylsilyl)thiazole

tert-butyl (4S,5R)-4-(cyclohexylmethyl)-5-formyl-2,2-dimethyl-3-oxazolidinecarboxylate

2-<(4S,5R)-3-tert-butoxycarbonyl-4-cyclohexylmethyl-2,2-dimethyl-1,3-oxazolidin-5-yl>-1,3-thiazole

Downstream raw materials:

(4S,5R)-5-((R)-1-Benzyloxy-2-oxo-ethyl)-4-cyclohexylmethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

(4S,5R)-5-((R)-Benzyloxy-thiazol-2-yl-methyl)-4-cyclohexylmethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester