(3S,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-pentanal

Base Information

• Chemical Name: (3S,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-pentanal
• CAS No.: 263761-21-3
• Molecular Formula: C₁₉H₃₂O₄Si
• Molecular Weight: 352.546
• Mol file: 263761-21-3.mol

Synonyms:(3S,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-pentanal

Chemical Property of (3S,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-pentanal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-pentanal

There total 2 articles about (3S,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-pentanal 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: 98.0%

tert-butyl(((2S,3S)-2-((4-methoxybenzyl)oxy)-hex-5-en-3-yl)oxy)dimethylsilane (263761-20-2) → (3S,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-pentanal (263761-21-3)

Guidance literature:

tert-butyl(((2S,3S)-2-((4-methoxybenzyl)oxy)-hex-5-en-3-yl)oxy)dimethylsilane; With ozone; In methanol; dichloromethane; at -78 ℃;

With triphenylphosphine; In methanol; dichloromethane; at -78 - 25 ℃; Further stages.;

DOI:10.1002/1521-3765(20010518)7:10<2261::AID-CHEM2261>3.0.CO;2-F

Reference yield:

(4S,5S)-4-hydroxy-5-(4-methoxybenzyloxy)-1-hexene (214892-50-9) → (3S,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-pentanal (263761-21-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 97 percent / imidazole / dimethylformamide / 16 h / 22 °C

2.1: O₃ / methanol; CH₂Cl₂ / -78 °C

2.2: 98 percent / PPh₃ / methanol; CH₂Cl₂ / -78 - 25 °C

With 1H-imidazole; ozone; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/1521-3765(20010518)7:10<2261::AID-CHEM2261>3.0.CO;2-F

Reference yield: 91.0%

isopropenylmagnesium bromide (13291-18-4) + (3S,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-pentanal (263761-21-3) → (5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-2-methyl-hept-1-en-3-ol (263761-04-2)

Guidance literature:

DOI:10.1007/s007060070099

upstream raw materials:

tert-butyl(((2S,3S)-2-((4-methoxybenzyl)oxy)-hex-5-en-3-yl)oxy)dimethylsilane

(4S,5S)-4-hydroxy-5-(4-methoxybenzyloxy)-1-hexene

Downstream raw materials:

(5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-2-methyl-hept-1-en-3-ol

epothilone B

(5S,6S)-6-(4-Methoxy-benzyloxy)-2-methyl-hept-1-ene-3,5-diol

1-{(4R,6S)-6-[(S)-1-(4-Methoxy-benzyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethanone