(3R,4S)-4-tert-butyldimethylsilyloxy-3-tert-butyldiphenylsilyloxy-1-pentene

Base Information

• Chemical Name: (3R,4S)-4-tert-butyldimethylsilyloxy-3-tert-butyldiphenylsilyloxy-1-pentene
• CAS No.: 1174412-62-4
• Molecular Formula: C₂₇H₄₂O₂Si₂
• Molecular Weight: 454.8
• Mol file: 1174412-62-4.mol

Synonyms:(3R,4S)-4-tert-butyldimethylsilyloxy-3-tert-butyldiphenylsilyloxy-1-pentene

Chemical Property of (3R,4S)-4-tert-butyldimethylsilyloxy-3-tert-butyldiphenylsilyloxy-1-pentene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4S)-4-tert-butyldimethylsilyloxy-3-tert-butyldiphenylsilyloxy-1-pentene

There total 4 articles about (3R,4S)-4-tert-butyldimethylsilyloxy-3-tert-butyldiphenylsilyloxy-1-pentene 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: 82.0%

tert-butylchlorodiphenylsilane (58479-61-1) + (3R,4S)-4-(tert-butyldimethylsilanyloxy)-pent-1-en-3-ol (132055-83-5) → (3R,4S)-4-tert-butyldimethylsilyloxy-3-tert-butyldiphenylsilyloxy-1-pentene (1174412-62-4)

Guidance literature:

With dmap; In N,N-dimethyl-formamide; at 0 - 50 ℃; for 24h; Inert atmosphere;

DOI:10.1016/j.tet.2011.08.014

Reference yield:

methyl (S)-2-(tert-butyldimethylsiloxy)propanoate (87681-24-1) → (3R,4S)-4-tert-butyldimethylsilyloxy-3-tert-butyldiphenylsilyloxy-1-pentene (1174412-62-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: diisobutylaluminium hydride / hexane; dichloromethane / 1.5 h / -78 - -30 °C / Inert atmosphere

2.1: tetrahydrofuran; hexane; dichloromethane / 1.5 h / -78 - 0 °C / Inert atmosphere

2.2: Inert atmosphere; Saturated solution

3.1: dmap / N,N-dimethyl-formamide / 24 h / 0 - 50 °C / Inert atmosphere

With dmap; diisobutylaluminium hydride; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2011.08.014

Reference yield:

(S)-2-tert-butyl-dimethyl-silanyloxy propanal (87727-28-4) → (3R,4S)-4-tert-butyldimethylsilyloxy-3-tert-butyldiphenylsilyloxy-1-pentene (1174412-62-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: tetrahydrofuran; hexane; dichloromethane / 1.5 h / -78 - 0 °C / Inert atmosphere

1.2: Inert atmosphere; Saturated solution

2.1: dmap / N,N-dimethyl-formamide / 24 h / 0 - 50 °C / Inert atmosphere

With dmap; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2011.08.014

upstream raw materials:

tert-butylchlorodiphenylsilane

(3R,4S)-4-(tert-butyldimethylsilanyloxy)-pent-1-en-3-ol

methyl (S)-2-(tert-butyldimethylsiloxy)propanoate

(S)-2-tert-butyl-dimethyl-silanyloxy propanal

Downstream raw materials:

(2R,3S)-3-tert-butyldiphenylsilyloxy-4-penten-2-ol

(S)-2-[(1S,2R)-2-hydroxy-1-methyl-3-butenyloxycarbonyl]-1-methylethyl (2E,4R,5S)-5-(N-acryloyl-N-benzylamino)-4-(2-methoxyethoxy)methoxy-2-hexenoate

(S)-2-[(1S,2R)-2-hydroxy-1-methyl-3-butenyloxycarbonyl]-1-methylethyl (2E,4R,5S)-5-(N-acryloyl-N-phenethylamino)-4-(2-methoxyethoxy)methoxy-2-hexenoate

(1S,2R,3E)-4-[(1S,2R)-2-tert-butyldiphenylsilyloxy-1-methyl-3-butenyloxy]-2-(methoxy-ethoxy)methoxy-1-methyl-3-butenyl (S)-3-benzylamino-butenoate