(S)-3-((tert-butyldiphenylsilyl)oxy)-14-methylpentadecanal

Base Information

• Chemical Name: (S)-3-((tert-butyldiphenylsilyl)oxy)-14-methylpentadecanal
• CAS No.: 1402050-29-6
• Molecular Formula: C₃₂H₅₀O₂Si
• Molecular Weight: 494.833
• Mol file: 1402050-29-6.mol

Synonyms:

Chemical Property of (S)-3-((tert-butyldiphenylsilyl)oxy)-14-methylpentadecanal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-3-((tert-butyldiphenylsilyl)oxy)-14-methylpentadecanal

There total 5 articles about (S)-3-((tert-butyldiphenylsilyl)oxy)-14-methylpentadecanal 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:

C35H58NOSSi(1+)*CF3O3S(1-) → (S)-3-((tert-butyldiphenylsilyl)oxy)-14-methylpentadecanal (1402050-29-6) + C32H50O2Si

Guidance literature:

With Li⁽¹⁺⁾*AlH₄^(1-)*3C₄H₁₀O; In tetrahydrofuran; dichloromethane; at -78 ℃; for 4h;

DOI:10.1021/jo301803h DOI:10.1021/jo301803h

Reference yield:

C39H62NOSSi(1+)*CF3O3S(1-) → (S)-3-((tert-butyldiphenylsilyl)oxy)-14-methylpentadecanal (1402050-29-6) + C32H50O2Si

Guidance literature:

With Li⁽¹⁺⁾*AlH₄^(1-)*3C₄H₁₀O; In tetrahydrofuran; dichloromethane; at -78 ℃; for 4h; Overall yield = 72 %; Overall yield = 71.1 mg;

DOI:10.1021/jo301803h DOI:10.1021/jo301803h

Reference yield:

(S)-3-hydroxy-N,N,14-trimethylpentadecanethioamide (1402050-26-3) → (S)-3-((tert-butyldiphenylsilyl)oxy)-14-methylpentadecanal (1402050-29-6) + C32H50O2Si

Guidance literature:

Multi-step reaction with 3 steps

1: 2,6-dimethylpyridine / dichloromethane / 2 h / 0 °C

2: diethyl ether / 4.5 h / 0 - 20 °C

3: Li⁽¹⁺⁾*AlH₄^(1-)*3C₄H₁₀O / tetrahydrofuran; dichloromethane / 4 h / -78 °C

With 2,6-dimethylpyridine; Li⁽¹⁺⁾*AlH₄^(1-)*3C₄H₁₀O; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1021/jo301803h DOI:10.1021/jo301803h

upstream raw materials:

12-methyltridecan-1-al

(S)-3-hydroxy-N,N,14-trimethylpentadecanethioamide

(S)-3-((tert-butyldiphenylsilyl)oxy)-N,N,14-trimethylpentadecanethioamide

Refernces

• 1、 Gopinath, Purushothaman,Watanabe, Takumi,Shibasaki, Masakatsu. "Studies on catalytic enantioselective total synthesis of caprazamycin B: Construction of the western zone". . p. 9260 - 9267. Retrieved 2013/01/15.