(2S,3R)-2-(t-butoxycarbonylamino)-3-cyclohexyl-3-hydroxypropanoic acid

Base Information

• Chemical Name: (2S,3R)-2-(t-butoxycarbonylamino)-3-cyclohexyl-3-hydroxypropanoic acid
• CAS No.: 82655-29-6
• Molecular Formula: C₁₄H₂₅NO₅
• Molecular Weight: 287.356
• Mol file: 82655-29-6.mol

Synonyms:(2S,3R)-2-(t-butoxycarbonylamino)-3-cyclohexyl-3-hydroxypropanoic acid

Chemical Property of (2S,3R)-2-(t-butoxycarbonylamino)-3-cyclohexyl-3-hydroxypropanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-2-(t-butoxycarbonylamino)-3-cyclohexyl-3-hydroxypropanoic acid

There total 12 articles about (2S,3R)-2-(t-butoxycarbonylamino)-3-cyclohexyl-3-hydroxypropanoic acid 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:

di-tert-butyl dicarbonate (24424-99-5) + C16H23NO3 → (2S,3R)-2-(t-butoxycarbonylamino)-3-cyclohexyl-3-hydroxypropanoic acid (82655-29-6)

Guidance literature:

C₁₆H₂₃NO₃; With 20 % Pd(OH)2/C; hydrogen; sodium hydroxide; In methanol; for 2.5h;

di-tert-butyl dicarbonate; In methanol; Inert atmosphere;

With potassium hydrogensulfate; In water; pH=3;

DOI:10.1016/j.bmc.2011.05.022

Reference yield:

(4S,5R)-3-benzyl-5-cyclohexyl-4-(hydroxymethyl)oxazolidin-2-one (1280013-85-5) → (2S,3R)-2-(t-butoxycarbonylamino)-3-cyclohexyl-3-hydroxypropanoic acid (82655-29-6)

Guidance literature:

Multi-step reaction with 6 steps

1: Jones reagent / acetone

2: diethyl ether

3: potassium hydroxide / ethanol

4: potassium hydroxide

5: 20 % Pd(OH)2/C; hydrogen

With Jones reagent; 20 % Pd(OH)2/C; hydrogen; potassium hydroxide; In diethyl ether; ethanol; acetone;

DOI:10.1016/j.bmcl.2010.12.109

Reference yield:

(4R,5R)-3-benzyl-5-cyclohexyl-2-oxo-oxazolidine-4-carboxylic acid (1280013-86-6) → (2S,3R)-2-(t-butoxycarbonylamino)-3-cyclohexyl-3-hydroxypropanoic acid (82655-29-6)

Guidance literature:

Multi-step reaction with 5 steps

1: diethyl ether

2: potassium hydroxide / ethanol

3: potassium hydroxide

4: 20 % Pd(OH)2/C; hydrogen

With 20 % Pd(OH)2/C; hydrogen; potassium hydroxide; In diethyl ether; ethanol;

DOI:10.1016/j.bmcl.2010.12.109

upstream raw materials:

(4S,5R)-3-benzyl-5-cyclohexyl-4-(hydroxymethyl)oxazolidin-2-one

(4R,5R)-3-benzyl-5-cyclohexyl-2-oxo-oxazolidine-4-carboxylic acid

(4S,5R)-3-benzyl-5-cyclohexyl-2-oxo-oxazolidine-4-carboxylic acid

di-tert-butyl dicarbonate

Downstream raw materials:

C₂₆H₃₉N₃O₃

4-[4-(((3S)-1-butyl-3-[(R)-cyclohexyl(hydroxy)methyl]-2,5-dioxo-1,4,9-triazaspiro[5.5]undec-9-yl)methyl)phenoxy]benzoic acid hydrochloride

C₃₃H₄₃N₃O₆

C₁₉H₃₃N₃O₃