(1R,2R)-2-[(tert-butyldiphenylsilyloxy)methyl]-1-(3-methyl-1-butanoyl)cyclopropane

Base Information

• Chemical Name: (1R,2R)-2-[(tert-butyldiphenylsilyloxy)methyl]-1-(3-methyl-1-butanoyl)cyclopropane
• CAS No.: 534585-41-6
• Molecular Formula: C₂₅H₃₄O₂Si
• Molecular Weight: 394.629
• Mol file: 534585-41-6.mol

Synonyms:(1R,2R)-2-[(tert-butyldiphenylsilyloxy)methyl]-1-(3-methyl-1-butanoyl)cyclopropane

Chemical Property of (1R,2R)-2-[(tert-butyldiphenylsilyloxy)methyl]-1-(3-methyl-1-butanoyl)cyclopropane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2R)-2-[(tert-butyldiphenylsilyloxy)methyl]-1-(3-methyl-1-butanoyl)cyclopropane

There total 2 articles about (1R,2R)-2-[(tert-butyldiphenylsilyloxy)methyl]-1-(3-methyl-1-butanoyl)cyclopropane 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: 74.0%

(1R,2R)-2-(tert-butyldiphenylsilyloxy)methyl-1-formylcyclopropane (408348-31-2) → (1R,2R)-2-[(tert-butyldiphenylsilyloxy)methyl]-1-(3-methyl-1-butanoyl)cyclopropane (534585-41-6)

Guidance literature:

(1R,2R)-2-(tert-butyldiphenylsilyloxy)methyl-1-formylcyclopropane; (CH₃)2CHCH₂MgHal; In tetrahydrofuran; at 20 ℃; for 5h;

With dipyridinium dichromate; 5A molecular sieve; In dichloromethane; at 20 ℃; for 5h;

DOI:10.1021/jo030019v

Reference yield:

(1R,2R)-2-<<(tert-Butyldiphenylsilyl)oxy>methyl>-1-(hydroxymethyl)cyclopropane (154001-59-9) → (1R,2R)-2-[(tert-butyldiphenylsilyloxy)methyl]-1-(3-methyl-1-butanoyl)cyclopropane (534585-41-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: oxalyl chloride; DMSO; triethylamine / CH₂Cl₂

2.1: tetrahydrofuran / 5 h / 20 °C

2.2: 74 percent / PDC; molecular sieves 5 Angstroem / CH₂Cl₂ / 5 h / 20 °C

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; 1.1: Swern oxidation;

DOI:10.1021/jo030019v

Reference yield:

(1R,2R)-2-[(tert-butyldiphenylsilyloxy)methyl]-1-(3-methyl-1-butanoyl)cyclopropane (534585-41-6) → (1R,2R)-2-[(tert-butyldiphenylsilyloxy)methyl]-1-[(R)-1-hydroxy-3-methylbutyl]cyclopropane + (1R,2R)-2-[(tert-butyldiphenylsilyloxy)methyl]-1-[(S)-1-hydroxy-3-methylbutyl]cyclopropane (534585-07-4)

Guidance literature:

With potassium tri-sec-butyl-borohydride; In tetrahydrofuran; dichloromethane; at -78 ℃; for 5h; Title compound not separated from byproducts;

DOI:10.1021/jo030019v

upstream raw materials:

(1R,2R)-2-(tert-butyldiphenylsilyloxy)methyl-1-formylcyclopropane

(1R,2R)-2-<<(tert-Butyldiphenylsilyl)oxy>methyl>-1-(hydroxymethyl)cyclopropane

Downstream raw materials:

(1R,2R)-2-[(tert-butyldiphenylsilyloxy)methyl]-1-[(S)-1-hydroxy-3-methylbutyl]cyclopropane