(1'S,2'R)-methyl N-(benzyloxy)carbonyl-2-[1-amino-2-(tert-butyldimethylsilyloxy)prop-1-yl]-5-methyloxazole-4-carboxylate

Base Information

• Chemical Name: (1'S,2'R)-methyl N-(benzyloxy)carbonyl-2-[1-amino-2-(tert-butyldimethylsilyloxy)prop-1-yl]-5-methyloxazole-4-carboxylate
• CAS No.: 875011-76-0
• Molecular Formula: C₂₃H₃₄N₂O₆Si
• Molecular Weight: 462.618
• Mol file: 875011-76-0.mol

Synonyms:(1'S,2'R)-methyl N-(benzyloxy)carbonyl-2-[1-amino-2-(tert-butyldimethylsilyloxy)prop-1-yl]-5-methyloxazole-4-carboxylate

Chemical Property of (1'S,2'R)-methyl N-(benzyloxy)carbonyl-2-[1-amino-2-(tert-butyldimethylsilyloxy)prop-1-yl]-5-methyloxazole-4-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1'S,2'R)-methyl N-(benzyloxy)carbonyl-2-[1-amino-2-(tert-butyldimethylsilyloxy)prop-1-yl]-5-methyloxazole-4-carboxylate

There total 6 articles about (1'S,2'R)-methyl N-(benzyloxy)carbonyl-2-[1-amino-2-(tert-butyldimethylsilyloxy)prop-1-yl]-5-methyloxazole-4-carboxylate 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: 52.0%

(4S,5S,1'S,2'R)-methyl N-(benzyloxy)carbonyl-2-[1-amino-2-(tert-butyldimethylsilyloxy)prop-1-yl]-5-methyloxazoline-4-carboxylate → (1'S,2'R)-methyl N-(benzyloxy)carbonyl-2-[1-amino-2-(tert-butyldimethylsilyloxy)prop-1-yl]-5-methyloxazole-4-carboxylate (875011-76-0)

Guidance literature:

With Bromotrichloromethane; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at -20 ℃; for 18h;

DOI:10.1016/j.tet.2005.09.134

Reference yield:

(2S,3R)-2-[(2S,3R)-2-Benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-butyrylamino]-3-hydroxy-butyric acid methyl ester (875011-74-8) → (1'S,2'R)-methyl N-(benzyloxy)carbonyl-2-[1-amino-2-(tert-butyldimethylsilyloxy)prop-1-yl]-5-methyloxazole-4-carboxylate (875011-76-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 65 percent / [bis(2-methoxyethyl)amino]sulfur trifluoride / CH₂Cl₂ / 18 h / -20 °C

2: 52 percent / BrCCl₃; DBU / CH₂Cl₂ / 18 h / -20 °C

With Bromotrichloromethane; 1,8-diazabicyclo[5.4.0]undec-7-ene; (bis-(2-methoxyethyl)amino)sulfur trufluoride; In dichloromethane;

DOI:10.1016/j.tet.2005.09.134

Reference yield:

methyl (2S,3R)-2-(benzyloxycarbonylamino)-3-hydroxybutyrate (57224-63-2) → (1'S,2'R)-methyl N-(benzyloxy)carbonyl-2-[1-amino-2-(tert-butyldimethylsilyloxy)prop-1-yl]-5-methyloxazole-4-carboxylate (875011-76-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 100 percent / imidazole; DMAP / dimethylformamide / 36 h / 20 °C

2: 96 percent / lithium hydroxide monohydrate / methanol; H₂O / 18 h / 20 °C

3: 83 percent / triethylamine; pyBOP / CH₂Cl₂ / 18 h / 0 - 20 °C

4: 65 percent / [bis(2-methoxyethyl)amino]sulfur trifluoride / CH₂Cl₂ / 18 h / -20 °C

5: 52 percent / BrCCl₃; DBU / CH₂Cl₂ / 18 h / -20 °C

With 1H-imidazole; dmap; lithium hydroxide; Bromotrichloromethane; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; (bis-(2-methoxyethyl)amino)sulfur trufluoride; In methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2005.09.134

upstream raw materials:

(2S,3R)-2-[(2S,3R)-2-Benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-butyrylamino]-3-hydroxy-butyric acid methyl ester

methyl (2S,3R)-2-(benzyloxycarbonylamino)-3-hydroxybutyrate

(2S,3R)-2-(benzyloxycarbonylamino)-3-tertiary-butyldimethylsilyloxybutanoic acid

(2S,3R)-methyl 2-(((benzyloxy)carbonyl)amino)-3-((tert-butyldimethylsilyl)oxy)butanoate