(S)-3-((tert-butyldimethylsilyl)oxy)-4-((tert-butyldiphenylsilyl)oxy)butanal

Base Information

• Chemical Name: (S)-3-((tert-butyldimethylsilyl)oxy)-4-((tert-butyldiphenylsilyl)oxy)butanal
• CAS No.: 157758-30-0
• Molecular Formula: C₂₆H₄₀O₃Si₂
• Molecular Weight: 456.773
• Mol file: 157758-30-0.mol

Synonyms:(S)-3-((tert-butyldimethylsilyl)oxy)-4-((tert-butyldiphenylsilyl)oxy)butanal

Chemical Property of (S)-3-((tert-butyldimethylsilyl)oxy)-4-((tert-butyldiphenylsilyl)oxy)butanal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-3-((tert-butyldimethylsilyl)oxy)-4-((tert-butyldiphenylsilyl)oxy)butanal

There total 1 articles about (S)-3-((tert-butyldimethylsilyl)oxy)-4-((tert-butyldiphenylsilyl)oxy)butanal 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:

(S)-methyl 4-(tert-butyldiphenylsilyloxy)-3-hydroxybutanoate (124655-05-6) → (S)-3-((tert-butyldimethylsilyl)oxy)-4-((tert-butyldiphenylsilyl)oxy)butanal (157758-30-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 25 °C

2: 96 percent / DIBAL, MeOH / CH₂Cl₂ / 0.5 h / -78 °C

With 2,6-dimethylpyridine; methanol; diisobutylaluminium hydride; In dichloromethane;

DOI:10.1039/c39940001147

Reference yield: 54.0%

tert-butyldimethylsilyl hex-5-yn-1-yl ether (73448-13-2) + (S)-3-((tert-butyldimethylsilyl)oxy)-4-((tert-butyldiphenylsilyl)oxy)butanal (157758-30-0) → (6S,8S)-6-((tert-butyldimethylsilyl)oxy)-2,2,16,16,17,17-hexamethyl-3,3-diphenyl-4,15-dioxa-3,16-disilaoctadec-9-yn-8-ol (1093663-69-4) + (6S,8R)-6-((tert-butyldimethylsilyl)oxy)-2,2,16,16,17,17-hexamethyl-3,3-diphenyl-4,15-dioxa-3,16-disilaoctadec-9-yn-8-ol (1093663-71-8)

Guidance literature:

tert-butyldimethylsilyl hex-5-yn-1-yl ether; With n-butyllithium; In tetrahydrofuran; hexane; at -78 - -30 ℃; Inert atmosphere;

(S)-3-((tert-butyldimethylsilyl)oxy)-4-((tert-butyldiphenylsilyl)oxy)butanal; In tetrahydrofuran; hexane; at -78 - 20 ℃; Inert atmosphere;

With water; sodium hydrogencarbonate; In tetrahydrofuran; diethyl ether; hexane; Inert atmosphere;

DOI:10.1021/ol802491m

Reference yield:

(-)-4-acetyl-3-(4-methoxybenzyl)-thiazolidinon-2-one (101860-51-9) + (S)-3-((tert-butyldimethylsilyl)oxy)-4-((tert-butyldiphenylsilyl)oxy)butanal (157758-30-0) → C39H55NO6SSi2 + C39H55NO6SSi2

Guidance literature:

(-)-4-acetyl-3-(4-methoxybenzyl)-thiazolidinon-2-one; With titanium tetrachloride; In dichloromethane; at -78 ℃; for 0.166667h;

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at -78 - 0 ℃; for 3h;

(S)-3-((tert-butyldimethylsilyl)oxy)-4-((tert-butyldiphenylsilyl)oxy)butanal; In dichloromethane; at -78 ℃; for 3h; Overall yield = 88 %; Overall yield = 0.71 g; Optical yield = 42.857 %de;

DOI:10.1021/ol503465p

upstream raw materials:

(S)-methyl 4-(tert-butyldiphenylsilyloxy)-3-hydroxybutanoate

Downstream raw materials:

(3S,4S,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxy)-3-methyl-hept-1-en-4-ol

C₃₁H₅₀O₃Si₂

1-[(2S,3S,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxy)-3-methoxy-2-methyl-hexyloxymethyl]-4-methoxy-benzene

(6S,8S)-6-((tert-butyldimethylsilyl)oxy)-2,2,16,16,17,17-hexamethyl-3,3-diphenyl-4,15-dioxa-3,16-disilaoctadec-9-yn-8-ol