(Z)-(4S,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxy)-4,6-dimethyl-hept-2-enal

Base Information

• Chemical Name: (Z)-(4S,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxy)-4,6-dimethyl-hept-2-enal
• CAS No.: 475051-48-0
• Molecular Formula: C₃₁H₄₈O₃Si₂
• Molecular Weight: 524.891
• Mol file: 475051-48-0.mol

Synonyms:(Z)-(4S,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxy)-4,6-dimethyl-hept-2-enal

Chemical Property of (Z)-(4S,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxy)-4,6-dimethyl-hept-2-enal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-(4S,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxy)-4,6-dimethyl-hept-2-enal

There total 8 articles about (Z)-(4S,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxy)-4,6-dimethyl-hept-2-enal 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: 86.0%

(Z)-(4S,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxy)-4,6-dimethyl-hept-2-en-1-ol (475051-60-6) → (Z)-(4S,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxy)-4,6-dimethyl-hept-2-enal (475051-48-0)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 - 0 ℃;

DOI:10.1016/S0040-4039(02)01389-8

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → (Z)-(4S,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxy)-4,6-dimethyl-hept-2-enal (475051-48-0)

Guidance literature:

Multi-step reaction with 8 steps

1: 87 percent / 2,6-lutidine / 1 h / 20 °C

2: DIBALH / CH₂Cl₂ / 3 h / -78 °C

3: 92 percent / imidazole / CH₂Cl₂ / 1 h / 20 °C

4: 90 percent / PTSA / methanol / 20 h / 20 °C

5: 87 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

6: 95 percent / 18-crown-6; KHMDS / tetrahydrofuran / 15 h / -78 °C

7: 90 percent / DIBALH / CH₂Cl₂ / 3 h / -78 °C

8: 86 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

With 1H-imidazole; 2,6-dimethylpyridine; oxalyl dichloride; 18-crown-6 ether; potassium hexamethylsilazane; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; 5: Swern oxidation / 6: Still reaction / 8: Swern oxidation;

DOI:10.1016/S0040-4039(02)01389-8

Reference yield:

(2R,3S,4S)-5-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-2,4-dimethyl-pentanoic acid ethyl ester (475051-45-7) → (Z)-(4S,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxy)-4,6-dimethyl-hept-2-enal (475051-48-0)

Guidance literature:

Multi-step reaction with 8 steps

1: 87 percent / 2,6-lutidine / 1 h / 20 °C

2: DIBALH / CH₂Cl₂ / 3 h / -78 °C

3: 92 percent / imidazole / CH₂Cl₂ / 1 h / 20 °C

4: 90 percent / PTSA / methanol / 20 h / 20 °C

5: 87 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

6: 95 percent / 18-crown-6; KHMDS / tetrahydrofuran / 15 h / -78 °C

7: 90 percent / DIBALH / CH₂Cl₂ / 3 h / -78 °C

8: 86 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

With 1H-imidazole; 2,6-dimethylpyridine; oxalyl dichloride; 18-crown-6 ether; potassium hexamethylsilazane; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; 5: Swern oxidation / 6: Still reaction / 8: Swern oxidation;

DOI:10.1016/S0040-4039(02)01389-8

upstream raw materials:

(Z)-(4S,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxy)-4,6-dimethyl-hept-2-en-1-ol

t-butyldimethylsiyl triflate

(2R,3S,4S)-5-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-2,4-dimethyl-pentanoic acid ethyl ester

(2R,3S,4S)-3,5-bis(tert-butyldimethylsilyloxy)-2,4-dimethylpentan-1-ol

Downstream raw materials:

phenyl (3R,4Z,6S,7S,8S)-7-(tert-butyldimethylsiloxy)-9-(tert-butyldilphenylsiloxy)-3-hydroxy-6,8-dimethyl-4-nonenoate

phenyl (3S,4Z,6S,7S,8S)-7-(tert-butyldimethylsiloxy)-9-(tert-butyldilphenylsiloxy)-3-hydroxy-6,8-dimethyl-4-nonenoate