(3R,5R,6E)-3,5-bis(tert-butyldimethylsilyloxy)-7-phenyl-6-heptenoic acid butyl ester

Base Information

• Chemical Name: (3R,5R,6E)-3,5-bis(tert-butyldimethylsilyloxy)-7-phenyl-6-heptenoic acid butyl ester
• CAS No.: 866324-11-0
• Molecular Formula: C₂₉H₅₂O₄Si₂
• Molecular Weight: 520.9
• Mol file: 866324-11-0.mol

Synonyms:(3R,5R,6E)-3,5-bis(tert-butyldimethylsilyloxy)-7-phenyl-6-heptenoic acid butyl ester

Chemical Property of (3R,5R,6E)-3,5-bis(tert-butyldimethylsilyloxy)-7-phenyl-6-heptenoic acid butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,5R,6E)-3,5-bis(tert-butyldimethylsilyloxy)-7-phenyl-6-heptenoic acid butyl ester

There total 1 articles about (3R,5R,6E)-3,5-bis(tert-butyldimethylsilyloxy)-7-phenyl-6-heptenoic acid butyl ester 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%

(5R,6E)-3,5-dihydroxy-7-phenyl-6-heptenoic acid butyl ester + tert-butyldimethylsilyl chloride (18162-48-6) → (3R,5R,6E)-3,5-bis(tert-butyldimethylsilyloxy)-7-phenyl-6-heptenoic acid butyl ester (866324-11-0) + (3S,5R,6E)-3,5-bis(tert-butyldimethylsilyloxy)-7-phenyl-6-heptenoic acid butyl ester

Guidance literature:

With 1H-imidazole; In dichloromethane; at 20 ℃; for 16h;

DOI:10.1021/ol051345v

Reference yield: 92.0%

(3R,5R,6E)-3,5-bis(tert-butyldimethylsilyloxy)-7-phenyl-6-heptenoic acid butyl ester (866324-11-0) → (3R,5R,6E)-3,5-bis{[tert-butyl(dimethyl)silyl]oxy}-7-phenylhept-6-enal (866324-09-6)

Guidance literature:

With diisobutylaluminium hydride; In dichloromethane; at -78 ℃; for 0.25h;

DOI:10.1021/ol051345v

Reference yield:

(3R,5R,6E)-3,5-bis(tert-butyldimethylsilyloxy)-7-phenyl-6-heptenoic acid butyl ester (866324-11-0) → 2-(2S,4R,6R(1E)-4-hydroxy-2-methoxy-6-(2-phenylethenyl)tetrahydro-2H-pyranylmethyl)oxazole-4-carboxylic acid methyl ester

Guidance literature:

Multi-step reaction with 4 steps

1: 92 percent / DIBAL / CH₂Cl₂ / 0.25 h / -78 °C

2: 66 percent / Sm; CH₂I₂ / tetrahydrofuran / 20 °C

3: 84 percent / trifluoroacetic anhydride; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

4: 86 percent / camphorsulfonic acid / 16 h / 20 °C

With samarium; diiodomethane; camphor-10-sulfonic acid; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; In tetrahydrofuran; dichloromethane; 2: Barbier coupling;

DOI:10.1021/ol051345v

upstream raw materials:

tert-butyldimethylsilyl chloride

Downstream raw materials:

(3R,5R,6E)-3,5-bis{[tert-butyl(dimethyl)silyl]oxy}-7-phenylhept-6-enal

2-[(4R,6R,7E)-4,6-bis(tert-butyldimethylsilyloxy)-2-oxo-8-phenyl-7-octenyl]oxazole-4-carboxylic acid methyl ester