Acetic acid (1R,3R)-3-benzyloxycarbonylamino-1-(tert-butyl-diphenyl-silanyloxymethyl)-3-phenyl-propyl ester

Base Information

• Chemical Name: Acetic acid (1R,3R)-3-benzyloxycarbonylamino-1-(tert-butyl-diphenyl-silanyloxymethyl)-3-phenyl-propyl ester
• CAS No.: 620990-03-6
• Molecular Formula: C₃₆H₄₁NO₅Si
• Molecular Weight: 595.811
• Mol file: 620990-03-6.mol

Synonyms:Acetic acid (1R,3R)-3-benzyloxycarbonylamino-1-(tert-butyl-diphenyl-silanyloxymethyl)-3-phenyl-propyl ester

Chemical Property of Acetic acid (1R,3R)-3-benzyloxycarbonylamino-1-(tert-butyl-diphenyl-silanyloxymethyl)-3-phenyl-propyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (1R,3R)-3-benzyloxycarbonylamino-1-(tert-butyl-diphenyl-silanyloxymethyl)-3-phenyl-propyl ester

There total 6 articles about Acetic acid (1R,3R)-3-benzyloxycarbonylamino-1-(tert-butyl-diphenyl-silanyloxymethyl)-3-phenyl-propyl 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: 65.0%

potassium acetate (127-08-2) + benzyl chloroformate (501-53-1,94274-21-2) + (4R,6S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-4-phenyl-[1,2,3]oxathiazinane 2,2-dioxide (620990-01-4) → Acetic acid (1R,3R)-3-benzyloxycarbonylamino-1-(tert-butyl-diphenyl-silanyloxymethyl)-3-phenyl-propyl ester (620990-03-6)

Guidance literature:

benzyl chloroformate; (4R,6S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-4-phenyl-[1,2,3]oxathiazinane 2,2-dioxide; With sodium t-butanolate;

potassium acetate; In N,N-dimethyl-formamide;

DOI:10.1016/j.tetlet.2003.08.006

Reference yield:

benzyltriphenylphosphonium chloride (1100-88-5) → Acetic acid (1R,3R)-3-benzyloxycarbonylamino-1-(tert-butyl-diphenyl-silanyloxymethyl)-3-phenyl-propyl ester (620990-03-6)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 80 percent / nBuLi

2.1: H₂ / Pd/C / methanol

3.1: pTSA / methanol

4.1: imidazole

5.1: 63 percent / chlorosulfonyl isocyanate; formic acid; pyridine / CH₂Cl₂ / 3 h / 25 °C

6.1: 73 percent / Rh₂(OAc)4; Mg₂O; PhI(OAc)2 / CH₂Cl₂ / 3 h / 40 °C

7.1: t-BuONa

7.2: 65 percent / dimethylformamide

With pyridine; 1H-imidazole; dirhodium tetraacetate; n-butyllithium; formic acid; isocyanate de chlorosulfonyle; [bis(acetoxy)iodo]benzene; hydrogen; magnesium oxide; toluene-4-sulfonic acid; sodium t-butanolate; palladium on activated charcoal; In methanol; dichloromethane; 1.1: Wittig olefination / 6.1: Du Bois nitrogen C-H insertion reaction;

DOI:10.1016/j.tetlet.2003.08.006

Reference yield:

(4S)-2,2-dimethyl-4-[(E)-2-phenylethenyl]-1,3-dioxolane (147976-19-0) → Acetic acid (1R,3R)-3-benzyloxycarbonylamino-1-(tert-butyl-diphenyl-silanyloxymethyl)-3-phenyl-propyl ester (620990-03-6)

Guidance literature:

Multi-step reaction with 6 steps

1.1: H₂ / Pd/C / methanol

2.1: pTSA / methanol

3.1: imidazole

4.1: 63 percent / chlorosulfonyl isocyanate; formic acid; pyridine / CH₂Cl₂ / 3 h / 25 °C

5.1: 73 percent / Rh₂(OAc)4; Mg₂O; PhI(OAc)2 / CH₂Cl₂ / 3 h / 40 °C

6.1: t-BuONa

6.2: 65 percent / dimethylformamide

With pyridine; 1H-imidazole; dirhodium tetraacetate; formic acid; isocyanate de chlorosulfonyle; [bis(acetoxy)iodo]benzene; hydrogen; magnesium oxide; toluene-4-sulfonic acid; sodium t-butanolate; palladium on activated charcoal; In methanol; dichloromethane; 5.1: Du Bois nitrogen C-H insertion reaction;

DOI:10.1016/j.tetlet.2003.08.006

upstream raw materials:

potassium acetate

benzyl chloroformate

(4R,6S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-4-phenyl-[1,2,3]oxathiazinane 2,2-dioxide

benzyltriphenylphosphonium chloride

Downstream raw materials:

(R)-tert-butyl (3-oxo-1-phenylpropyl)carbamate

(2R,4R)-4-Amino-4-phenyl-butane-1,2-diol