(2S,3S,4S)-2-bromo-3-tert-butyldimethylsilyloxymethyl-4-tert-butyldiphenylsilyloxycyclopentanone

Base Information

• Chemical Name: (2S,3S,4S)-2-bromo-3-tert-butyldimethylsilyloxymethyl-4-tert-butyldiphenylsilyloxycyclopentanone
• CAS No.: 1344673-90-0
• Molecular Formula: C₂₈H₄₁BrO₃Si₂
• Molecular Weight: 561.707
• Mol file: 1344673-90-0.mol

Synonyms:(2S,3S,4S)-2-bromo-3-tert-butyldimethylsilyloxymethyl-4-tert-butyldiphenylsilyloxycyclopentanone

Chemical Property of (2S,3S,4S)-2-bromo-3-tert-butyldimethylsilyloxymethyl-4-tert-butyldiphenylsilyloxycyclopentanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4S)-2-bromo-3-tert-butyldimethylsilyloxymethyl-4-tert-butyldiphenylsilyloxycyclopentanone

There total 3 articles about (2S,3S,4S)-2-bromo-3-tert-butyldimethylsilyloxymethyl-4-tert-butyldiphenylsilyloxycyclopentanone 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: 61.0%

C27H41BrO3Si2 → (2S,3S,4S)-2-bromo-3-tert-butyldimethylsilyloxymethyl-4-tert-butyldiphenylsilyloxycyclopentanone (1344673-90-0)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 20 ℃; Inert atmosphere;

DOI:10.1002/anie.201104447

Reference yield:

(1S,2S)-2-(tert-butyldimethylsilyl)oxymethylcyclopent-3-en-1-ol (1344673-87-5) → (2S,3S,4S)-2-bromo-3-tert-butyldimethylsilyloxymethyl-4-tert-butyldiphenylsilyloxycyclopentanone (1344673-90-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 1H-imidazole; dmap / dichloromethane; N,N-dimethyl-formamide / 20 °C / Inert atmosphere

2: N-Bromosuccinimide; water / acetone / 20 °C / Inert atmosphere

3: Dess-Martin periodane / dichloromethane / 20 °C / Inert atmosphere

With 1H-imidazole; dmap; N-Bromosuccinimide; water; Dess-Martin periodane; In dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1002/anie.201104447

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (2S,3S,4S)-2-bromo-3-tert-butyldimethylsilyloxymethyl-4-tert-butyldiphenylsilyloxycyclopentanone (1344673-90-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 1H-imidazole / dichloromethane / 0 °C / Inert atmosphere

2: 1H-imidazole; dmap / dichloromethane; N,N-dimethyl-formamide / 20 °C / Inert atmosphere

3: N-Bromosuccinimide; water / acetone / 20 °C / Inert atmosphere

4: Dess-Martin periodane / dichloromethane / 20 °C / Inert atmosphere

With 1H-imidazole; dmap; N-Bromosuccinimide; water; Dess-Martin periodane; In dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1002/anie.201104447

upstream raw materials:

(1S,2S)-2-(tert-butyldimethylsilyl)oxymethylcyclopent-3-en-1-ol

tert-butyldimethylsilyl chloride

Downstream raw materials:

2-[(2R,4S,5S,6R,7R)-7-[(E)-((2S,3S)-2-tert-butyldimethylsilyloxymethyl-3-tert-butyldiphenylsilyloxy-5-oxocyclopentylidene)methyl]-2-tert-butyldiphenylsilyloxymethyl-4,7-dimethyl-1-oxaspiro[4.4]non-6-yl]ethyl 2,2-dimethylpropanoate

2-[(2R,4S,5S,6R,7R)-7-[((1S,2S,3S)-2-tert-butyldimethylsilyloxymethyl-3-tert-butyldiphenylsilyloxy-5-oxocyclopentyl)methyl]-2-tert-butyldiphenylsilyloxymethyl-4,7-dimethyl-1-oxaspiro[4.4]non-6-yl]ethyl 2,2-dimethylpropanoate

(1R,2S,3S,4S)-3-tert-butyldimethylsilyloxymethyl-4-tert-butyldiphenylsilyloxy-2-{[(2R,4S,5S,6R,7R)-2-tert-butyldiphenylsilyloxymethyl-6-(2-hydroxyethyl)-4,7-dimethyl-1-oxaspiro[4.4]non-7-yl]methyl}-1-methylcyclopentanol

[(2R,4S,5S,6R,7R)-7-[((1S,2R,4S,5S)-5-tert-butyldimethylsilyloxymethyl-4-tert-butyldiphenylsilyloxy-2-hydroxy-2-methylcyclopentyl)methyl]-2-tert-butyldiphenylsilyloxymethyl-4,7-dimethyl-1-oxaspiro[4.4]non-6-yl]acetaldehyde

Refernces