(3R)-4-tert-butoxycarbonylamino-3-tert-butyldimethylsiloxy-1-(4-dimethoxymethylphenyl)butanone

Base Information

• Chemical Name: (3R)-4-tert-butoxycarbonylamino-3-tert-butyldimethylsiloxy-1-(4-dimethoxymethylphenyl)butanone
• CAS No.: 272786-26-2
• Molecular Formula: C₂₄H₄₁NO₆Si
• Molecular Weight: 467.678
• Mol file: 272786-26-2.mol

Synonyms:(3R)-4-tert-butoxycarbonylamino-3-tert-butyldimethylsiloxy-1-(4-dimethoxymethylphenyl)butanone

Chemical Property of (3R)-4-tert-butoxycarbonylamino-3-tert-butyldimethylsiloxy-1-(4-dimethoxymethylphenyl)butanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R)-4-tert-butoxycarbonylamino-3-tert-butyldimethylsiloxy-1-(4-dimethoxymethylphenyl)butanone

There total 1 articles about (3R)-4-tert-butoxycarbonylamino-3-tert-butyldimethylsiloxy-1-(4-dimethoxymethylphenyl)butanone 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: 72.0%

1,1-dimethoxy-1-(4-bromophenyl)methane (24856-58-4) + tert-butyl (R)-4-((tert-butyldimethylsilyl)oxy)-2-oxopyrrolidine-1-carboxylate (228267-20-7) → (3R)-4-tert-butoxycarbonylamino-3-tert-butyldimethylsiloxy-1-(4-dimethoxymethylphenyl)butanone (272786-26-2)

Guidance literature:

1,1-dimethoxy-1-(4-bromophenyl)methane; With magnesium; In tetrahydrofuran; at 70 ℃;

tert-butyl (R)-4-((tert-butyldimethylsilyl)oxy)-2-oxopyrrolidine-1-carboxylate; In tetrahydrofuran; at -30 ℃; for 0.5h;

With sodium hydroxide; In tetrahydrofuran; ethyl acetate; at 20 ℃; for 1.5h;

DOI:10.1248/cpb.49.1500

Reference yield: 95.0%

(3R)-4-tert-butoxycarbonylamino-3-tert-butyldimethylsiloxy-1-(4-dimethoxymethylphenyl)butanone (272786-26-2) → (1S,3R)-4-tert-butoxycarbonylamino-3-tert-butyldimethylsiloxy-1-(4-dimethoxymethylphenyl)butanol (312297-44-2)

Guidance literature:

With dimethylsulfide borane complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; at 20 ℃; for 0.333333h;

DOI:10.1248/cpb.49.1500

Reference yield:

(3R)-4-tert-butoxycarbonylamino-3-tert-butyldimethylsiloxy-1-(4-dimethoxymethylphenyl)butanone (272786-26-2) → (1S,3R)-4-tert-butoxycarbonylamino-3-tert-butyldimethylsiloxy-1-(4-dimethoxymethylphenyl)butanol (312297-44-2) + (1R,3R)-4-tert-butoxycarbonylamino-3-tert-butyldimethylsiloxy-1-(4-dimethoxymethylphenyl)butanol

Guidance literature:

With sodium tetrahydroborate; In tetrahydrofuran; methanol; at -10 ℃;

DOI:10.1016/S0040-4020(00)00685-2

upstream raw materials:

1,1-dimethoxy-1-(4-bromophenyl)methane

tert-butyl (R)-4-((tert-butyldimethylsilyl)oxy)-2-oxopyrrolidine-1-carboxylate

Downstream raw materials:

(1S,3R)-4-tert-butoxycarbonylamino-3-tert-butyldimethylsiloxy-1-(4-dimethoxymethylphenyl)butanol

(2R,4R)-1-tert-butoxycarbonyl-4-tert-butyldimethylsiloxy-2-(4-formylphenyl)pyrrolidine

4-(tert-butyl-dimethyl-silanyloxy)-2-(4-dimethoxymethyl-phenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester