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

Base Information

• Chemical Name: (1S,2S)-2-(tert-butyldiphenylsilyloxy)methyl-1-formylcyclopropane
• CAS No.: 408348-59-4
• Molecular Formula: C₂₁H₂₆O₂Si
• Molecular Weight: 338.522
• Mol file: 408348-59-4.mol

Synonyms:(1S,2S)-2-(tert-butyldiphenylsilyloxy)methyl-1-formylcyclopropane

Chemical Property of (1S,2S)-2-(tert-butyldiphenylsilyloxy)methyl-1-formylcyclopropane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2S)-2-(tert-butyldiphenylsilyloxy)methyl-1-formylcyclopropane

There total 5 articles about (1S,2S)-2-(tert-butyldiphenylsilyloxy)methyl-1-formylcyclopropane 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:

(1S,2S)-1-(tert-butyldiphenylsilanyloxy)methyl-2-hydroxymethylcyclopropane (408348-57-2) → (1S,2S)-2-(tert-butyldiphenylsilyloxy)methyl-1-formylcyclopropane (408348-59-4)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 ℃;

DOI:10.1021/jo010852x

Reference yield:

(1S,5R)-2-oxo-1-phenylsulfonyl-3-oxabicyclo[3.1.0]hexane (409307-02-4) → (1S,2S)-2-(tert-butyldiphenylsilyloxy)methyl-1-formylcyclopropane (408348-59-4)

Guidance literature:

Multi-step reaction with 4 steps

1: NaBH₄ / methanol; tetrahydrofuran / 20 °C

2: imidazole / dimethylformamide / -20 °C

3: Mg / methanol / 50 °C

4: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

With 1H-imidazole; sodium tetrahydroborate; oxalyl dichloride; magnesium; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 4: Swern oxidation;

DOI:10.1021/jo010852x

Reference yield:

(1R,2S)-2-Benzenesulfonyl-2-hydroxymethyl-cyclopropanecarbonitrile → (1S,2S)-2-(tert-butyldiphenylsilyloxy)methyl-1-formylcyclopropane (408348-59-4)

Guidance literature:

Multi-step reaction with 5 steps

1: aq. AcOH / 20 °C / pH 3

2: NaBH₄ / methanol; tetrahydrofuran / 20 °C

3: imidazole / dimethylformamide / -20 °C

4: Mg / methanol / 50 °C

5: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

With 1H-imidazole; sodium tetrahydroborate; oxalyl dichloride; magnesium; acetic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 5: Swern oxidation;

DOI:10.1021/jo010852x

upstream raw materials:

(1S,2S)-1-(tert-butyldiphenylsilanyloxy)methyl-2-hydroxymethylcyclopropane

(1S,5R)-2-oxo-1-phenylsulfonyl-3-oxabicyclo[3.1.0]hexane

(1S,2R)-1,2-bis(hydroxymethyl)-1-phenylsulfonylcyclopropane

(1S,2R)-2-(tert-butyldiphenylsilyloxy)methyl-1-hydroxymethyl-1-phenylsulfonylcyclopropane

Downstream raw materials:

(1R,2S)-2-(t-butyldiphenylsilyloxy)methyl-1-(2-hydroxyethyl)cyclopropane

(1R,2S)-2-[(tert-butyldiphenylsiloxy)methyl]-1-(formylmethyl)cyclopropane

(1S,2S)-2-[(tert-butyldiphenylsiloxy)methyl]-1-[((S)-tert-butylsulfinyl)iminomethyl]cyclopropane

(1S,2S)-2-[(tert-butyldiphenylsiloxy)methyl]-1-[((R)-tert-butylsulfinyl)iminomethyl]cyclopropane