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

Base Information

• Chemical Name: (1R,2S)-2-(tert-butyldiphenylsilyloxy)methyl-1-hydroxymethyl-1-phenylsulfonylcyclopropane
• CAS No.: 408348-30-1
• Molecular Formula: C₂₇H₃₂O₄SSi
• Molecular Weight: 480.7
• Mol file: 408348-30-1.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 4 articles about (1R,2S)-2-(tert-butyldiphenylsilyloxy)methyl-1-hydroxymethyl-1-phenylsulfonylcyclopropane 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: 84.0%

tert-butylchlorodiphenylsilane (58479-61-1) + (1R,2S)-1,2-bis(hydroxymethyl)-1-phenylsulfonylcyclopropane (408348-29-8) → (1R,2S)-2-(tert-butyldiphenylsilyloxy)methyl-1-hydroxymethyl-1-phenylsulfonylcyclopropane (408348-30-1)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at -20 ℃; for 5h;

DOI:10.1021/jo010852x

Reference yield:

2-(phenylsulfonyl)acetonitrile (7605-28-9) → (1R,2S)-2-(tert-butyldiphenylsilyloxy)methyl-1-hydroxymethyl-1-phenylsulfonylcyclopropane (408348-30-1)

Guidance literature:

Multi-step reaction with 4 steps

1: EtONa / ethanol / 12 h / 20 °C

2: 15.6 g / aq. AcOH / 5 h / 20 °C / pH 3

3: 71 percent / NaBH₄ / methanol; tetrahydrofuran / 12 h / 20 °C

4: 84 percent / imidazole / dimethylformamide / 5 h / -20 °C

With 1H-imidazole; sodium tetrahydroborate; sodium ethanolate; acetic acid; In tetrahydrofuran; methanol; ethanol; N,N-dimethyl-formamide;

DOI:10.1021/jo010852x

Reference yield:

(1R,5S)-1-(phenylsulfonyl)-3-oxabicyclo[3.1.0]hexan-2-one (408348-28-7) → (1R,2S)-2-(tert-butyldiphenylsilyloxy)methyl-1-hydroxymethyl-1-phenylsulfonylcyclopropane (408348-30-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 71 percent / NaBH₄ / methanol; tetrahydrofuran / 12 h / 20 °C

2: 84 percent / imidazole / dimethylformamide / 5 h / -20 °C

With 1H-imidazole; sodium tetrahydroborate; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1021/jo010852x

upstream raw materials:

tert-butylchlorodiphenylsilane

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

2-(phenylsulfonyl)acetonitrile

(1R,5S)-1-(phenylsulfonyl)-3-oxabicyclo[3.1.0]hexan-2-one