Methyl (6R)-tert-butyldiphenylsiloxy-7-methyloct-(2E,4E),7-trienoate

Base Information

• Chemical Name: Methyl (6R)-tert-butyldiphenylsiloxy-7-methyloct-(2E,4E),7-trienoate
• CAS No.: 139057-33-3
• Molecular Formula: C₂₆H₃₂O₃Si
• Molecular Weight: 420.624
• Mol file: 139057-33-3.mol

Synonyms:Methyl (6R)-tert-butyldiphenylsiloxy-7-methyloct-(2E,4E),7-trienoate

Chemical Property of Methyl (6R)-tert-butyldiphenylsiloxy-7-methyloct-(2E,4E),7-trienoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methyl (6R)-tert-butyldiphenylsiloxy-7-methyloct-(2E,4E),7-trienoate

There total 14 articles about Methyl (6R)-tert-butyldiphenylsiloxy-7-methyloct-(2E,4E),7-trienoate 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: 87.0%

(E)-(S)-6-(tert-Butyl-diphenyl-silanyloxy)-7-methyl-octa-2,7-dien-4-ynoic acid methyl ester (139057-29-7) → Methyl (6R)-tert-butyldiphenylsiloxy-7-methyloct-(2E,4E),7-trienoate (139057-33-3)

Guidance literature:

With quinoline; hydrogen; Lindlar's catalyst; In ethyl acetate; at 0 ℃; for 48h;

DOI:10.1248/cpb.39.2545

Reference yield:

2-(tert-Butyldiphenylsiloxy)-3-methyl-but-3-enal (97971-47-6) → Methyl (6R)-tert-butyldiphenylsiloxy-7-methyloct-(2E,4E),7-trienoate (139057-33-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 1) Ph₃P, 2) zinc powder / 1) CH₂Cl₂, 5 min, 0 deg C, 2) 3 h, r.t.

2: 1) n-BuLi 2) water / 1) hexane, THF, a) -78 deg C, 1h, b) 25 deg C, 1 h, 2) r.t., 30 min

3: 1) n-BuLi / 1) hexane, THF, 2 h, -78 deg C, 2) 4 h, -78 deg C

4: 1) NaH / 1) benzene, 30 min, r.t., 2) benzene, 30 min, r.t.

5: 87 percent / H₂, quinoline / Lindlar catalyst / ethyl acetate / 48 h / 0 °C

With quinoline; n-butyllithium; water; hydrogen; sodium hydride; triphenylphosphine; zinc; Lindlar's catalyst; In ethyl acetate;

DOI:10.1248/cpb.39.2545

Reference yield:

(3R)-tert-Butyldiphenylsilyloxy-4-methylpent-4-en-1-yne (139057-27-5) → Methyl (6R)-tert-butyldiphenylsiloxy-7-methyloct-(2E,4E),7-trienoate (139057-33-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 1) n-BuLi / 1) hexane, THF, 2 h, -78 deg C, 2) 4 h, -78 deg C

2: 1) NaH / 1) benzene, 30 min, r.t., 2) benzene, 30 min, r.t.

3: 87 percent / H₂, quinoline / Lindlar catalyst / ethyl acetate / 48 h / 0 °C

With quinoline; n-butyllithium; hydrogen; sodium hydride; Lindlar's catalyst; In ethyl acetate;

DOI:10.1248/cpb.39.2545

upstream raw materials:

trimethyl phosphonoacetate

4-(tert-Butyldiphenylsiloxy)-5-methylhexa-2(E),5-dienal

4-(tert-Butyldiphenylsiloxy)-5-methylhexa-2(E),5-dien-1-ol

Methyl 4-(tert-Butyldiphenylsiloxy)-5-methyl-hexa-2(E),5-dienoate

Downstream raw materials:

(2E,4E)-(R)-6-(tert-Butyl-diphenyl-silanyloxy)-6-((S)-2-methyl-oxiranyl)-hexa-2,4-dienoic acid methyl ester

(2E,4E)-(R)-6-(tert-Butyl-diphenyl-silanyloxy)-6-((R)-2-methyl-oxiranyl)-hexa-2,4-dienoic acid methyl ester

(2E,4E,6Z)-(R)-8-[(2R,3S)-2-(tert-Butyl-diphenyl-silanyloxy)-3-methyl-pentanoyloxy]-8-((S)-2-methyl-oxiranyl)-octa-2,4,6-trienoic acid methyl ester

Methyl (8R)-tert-butyldiphenylsiloxy-(9R),10-epoxy-9-methyldeca-(2E,4E,6Z)-trienoate