(1S,2R)-2-[(tert-butyldiphenylsilyloxy)methyl]-1-[(S)-1-hydroxyethyl]cyclopropane

Base Information

• Chemical Name: (1S,2R)-2-[(tert-butyldiphenylsilyloxy)methyl]-1-[(S)-1-hydroxyethyl]cyclopropane
• CAS No.: 534585-11-0
• Molecular Formula: C₂₂H₃₀O₂Si
• Molecular Weight: 354.565
• Mol file: 534585-11-0.mol

Synonyms:(1S,2R)-2-[(tert-butyldiphenylsilyloxy)methyl]-1-[(S)-1-hydroxyethyl]cyclopropane

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 10 articles about (1S,2R)-2-[(tert-butyldiphenylsilyloxy)methyl]-1-[(S)-1-hydroxyethyl]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:

tert-butylchlorodiphenylsilane (58479-61-1) + (1S,2R)-2-benzyloxymethyl-1-ethanoylcyclopropane (534585-47-2) → (1S,2R)-2-[(tert-butyldiphenylsilyloxy)methyl]-1-[(S)-1-hydroxyethyl]cyclopropane (534585-11-0) + (1S,2R)-2-[(tert-butyldiphenylsilyloxy)methyl]-1-[(R)-1-hydroxyethyl]cyclopropane

Guidance literature:

(1S,2R)-2-benzyloxymethyl-1-ethanoylcyclopropane; With potassium tri-sec-butyl-borohydride; In tetrahydrofuran; dichloromethane; at -78 ℃; for 1h;

With hydrogen; palladium on activated charcoal; In methanol;

tert-butylchlorodiphenylsilane; With 1H-imidazole; In N,N-dimethyl-formamide; Title compound not separated from byproducts;

DOI:10.1021/jo030019v

Reference yield:

(1S,2R)-2-[(tert-butyldiphenylsilyloxy)methyl]-1-(1-ethanoyl)cyclopropane (534585-42-7) → (1S,2R)-2-[(tert-butyldiphenylsilyloxy)methyl]-1-[(S)-1-hydroxyethyl]cyclopropane (534585-11-0) + (1S,2R)-2-[(tert-butyldiphenylsilyloxy)methyl]-1-[(R)-1-hydroxyethyl]cyclopropane

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; dichloromethane; at -78 ℃; for 1h; Title compound not separated from byproducts;

DOI:10.1021/jo030019v

Reference yield:

(1S,2R)-1-<methyl>-2-(hydroxymethyl)cyclopropane (133494-58-3) → (1S,2R)-2-[(tert-butyldiphenylsilyloxy)methyl]-1-[(S)-1-hydroxyethyl]cyclopropane (534585-11-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: NaH / tetrahydrofuran; various solvent(s) / 48 h / 20 °C

2.1: 246 mg / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / 20 °C

3.1: 69 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / 1.5 h / -78 °C

4.1: tetrahydrofuran / 5 h / 20 °C

5.1: 159 mg / PDC; molecular sieves 5 Angstroem / CH₂Cl₂ / 5 h / 20 °C

6.1: K-Selectride / CH₂Cl₂; tetrahydrofuran / 1 h / -78 °C

6.2: H₂ / Pd/C / methanol

6.3: imidazole / dimethylformamide

With dipyridinium dichromate; oxalyl dichloride; 5A molecular sieve; tetrabutyl ammonium fluoride; sodium hydride; potassium tri-sec-butyl-borohydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; 3.1: Swern oxidation;

DOI:10.1021/jo030019v

upstream raw materials:

methylmagnesium bromide

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

tert-butylchlorodiphenylsilane

(1S,2R)-2-benzyloxymethyl-1-ethanoylcyclopropane