Carbamic acid, [(1R,2R)-3-hydroxy-1-(hydroxymethyl)-2-methylpropyl]-, 1,1-

Base Information

• Chemical Name: Carbamic acid, [(1R,2R)-3-hydroxy-1-(hydroxymethyl)-2-methylpropyl]-, 1,1-
• CAS No.: 137106-00-4
• Molecular Formula: C10H21NO4
• Molecular Weight: 219.281
• Mol file: 137106-00-4.mol

Synonyms:Carbamic acid, [(1R,2R)-3-hydroxy-1-(hydroxymethyl)-2-methylpropyl]-, 1,1-

Chemical Property of Carbamic acid, [(1R,2R)-3-hydroxy-1-(hydroxymethyl)-2-methylpropyl]-, 1,1-

Chemical Property:

• PSA: 78.79000
• LogP: 0.89130

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Carbamic acid, [(1R,2R)-3-hydroxy-1-(hydroxymethyl)-2-methylpropyl]-, 1,1-

There total 8 articles about Carbamic acid, [(1R,2R)-3-hydroxy-1-(hydroxymethyl)-2-methylpropyl]-, 1,1- 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: 71.0%

di-tert-butyl dicarbonate (24424-99-5) + (R)-2-Amino-3-methyl-butane-1,4-diol → (2R,3R)-(3-hydroxy-1-hydroxymethyl-2-methyl-propyl)-carbamic acid tert-butyl ester (137106-00-4,734548-35-7)

Guidance literature:

With triethylamine; In dichloromethane; isopropyl alcohol; at 20 ℃; for 6h;

DOI:10.1021/ja0281840

Reference yield:

N-(tert-butoxycarbonyl)glycine methyl ester (31954-27-5) → (2R,3R)-(3-hydroxy-1-hydroxymethyl-2-methyl-propyl)-carbamic acid tert-butyl ester (137106-00-4,734548-35-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: N-bromosuccinimide

2.1: piperidinomethylpolystyrene / CH₂Cl₂ / 0.17 h / 20 °C

3.1: Cu(OTf)2; (R,R)-(o-MeC₆H₄-CH₂NHCHPh)2 / CH₂Cl₂ / 1 h / -20 °C

3.2: aq. HCl / tetrahydrofuran / 2 h / 20 °C

3.3: LiBNEt₃H / tetrahydrofuran / 0.5 h / 0 °C

With N-Bromosuccinimide; piperidinomethylpolystyrene; (1R,2R)-N,N’-bis(2-methylbenzyl)-1,2-diphenylethane-1,2-diamine; copper(II) bis(trifluoromethanesulfonate); In dichloromethane; 3.1: Mannich-type reaction;

DOI:10.1021/ol034717d

Reference yield:

(Z)-1-(tert-butylthio)-1-trimethylsilyloxyprop-1-ene (76943-94-7) + [(E)-tert-Butoxycarbonylimino]-acetic acid methyl ester (81357-15-5) → (2R,3R)-(3-hydroxy-1-hydroxymethyl-2-methyl-propyl)-carbamic acid tert-butyl ester (137106-00-4,734548-35-7) + (2S,3S)-syn-2-tert-butoxycarbonylamino-3-methylbutane-1,4-diol (137105-99-8,734548-35-7) + anti-2-tert-butoxycarbonylamino-3-methylbutane-1,4-diol (734548-35-7)

Guidance literature:

(Z)-1-(tert-butylthio)-1-trimethylsilyloxyprop-1-ene; [(E)-tert-Butoxycarbonylimino]-acetic acid methyl ester; With (1R,2R)-N,N’-bis(2-methylbenzyl)-1,2-diphenylethane-1,2-diamine; copper(II) bis(trifluoromethanesulfonate); In dichloromethane; at -20 ℃; for 1h;

With hydrogenchloride; In tetrahydrofuran; at 20 ℃; for 2h;

With LiBNEt₃H; In tetrahydrofuran; at 0 ℃; for 0.5h; Title compound not separated from byproducts;

DOI:10.1021/ol034717d

upstream raw materials:

(Z)-1-(tert-butylthio)-1-trimethylsilyloxyprop-1-ene

[(E)-tert-Butoxycarbonylimino]-acetic acid methyl ester

di-tert-butyl dicarbonate

N-(tert-butoxycarbonyl)glycine methyl ester

Downstream raw materials:

1-benzyl-3(R)-[(t-butoxycarbonyl)amino] - 4(S)-methylpyrrolidine