(S)-2-{(4S,6S)-6-[(Z)-(3S,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxy)-3,5-dimethyl-hex-1-enyl]-[1,3]dioxan-4-yl}-propionic acid ethyl ester

Base Information

• Chemical Name: (S)-2-{(4S,6S)-6-[(Z)-(3S,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxy)-3,5-dimethyl-hex-1-enyl]-[1,3]dioxan-4-yl}-propionic acid ethyl ester
• CAS No.: 475051-52-6
• Molecular Formula: C₃₉H₆₂O₆Si₂
• Molecular Weight: 683.089
• Mol file: 475051-52-6.mol

Synonyms:(S)-2-{(4S,6S)-6-[(Z)-(3S,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxy)-3,5-dimethyl-hex-1-enyl]-[1,3]dioxan-4-yl}-propionic acid ethyl ester

Chemical Property of (S)-2-{(4S,6S)-6-[(Z)-(3S,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxy)-3,5-dimethyl-hex-1-enyl]-[1,3]dioxan-4-yl}-propionic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-{(4S,6S)-6-[(Z)-(3S,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxy)-3,5-dimethyl-hex-1-enyl]-[1,3]dioxan-4-yl}-propionic acid ethyl ester

There total 6 articles about (S)-2-{(4S,6S)-6-[(Z)-(3S,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxy)-3,5-dimethyl-hex-1-enyl]-[1,3]dioxan-4-yl}-propionic acid ethyl ester 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: 85.0%

ethyl (2R,3S,5S,6Z,8S,9S,10S)-2-bromo-9-(tert-butyldimethylsiloxy)-11-(tert-butyldiphenylsiloxy)-2,8,10-trimethyl-3,5-methylenedioxy-6-undecenoate (475051-63-9) → (S)-2-{(4S,6S)-6-[(Z)-(3S,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxy)-3,5-dimethyl-hex-1-enyl]-[1,3]dioxan-4-yl}-propionic acid ethyl ester (475051-52-6)

Guidance literature:

With triethyl borane; tri-n-butyl-tin hydride; In toluene; at -78 ℃; for 3h;

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

Reference yield:

(3S,4Z,6S,7S,8S)-3,7-di-(tert-butyldimethylsiloxy)-9-(tert-butyldiphenylsiloxy)-6,8-dimethyl-4-nonenal (475051-50-4) → (S)-2-{(4S,6S)-6-[(Z)-(3S,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxy)-3,5-dimethyl-hex-1-enyl]-[1,3]dioxan-4-yl}-propionic acid ethyl ester (475051-52-6)

Guidance literature:

Multi-step reaction with 3 steps

1: BH₃*THF / chiral borane from L-TsVal / -78 °C

2: 80 percent / P₂O₅ / CHCl₃ / 1 h / 20 °C

3: 85 percent / Bu₃SnH; Et₃B / toluene / 3 h / -78 °C

With borane-THF; triethyl borane; tri-n-butyl-tin hydride; phosphorus pentoxide; chiral borane from L-TsVal; In chloroform; toluene;

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

Reference yield:

phenyl (3S,4Z,6S,7S,8S)-7-(tert-butyldimethylsiloxy)-9-(tert-butyldilphenylsiloxy)-3-hydroxy-6,8-dimethyl-4-nonenoate (475051-49-1) → (S)-2-{(4S,6S)-6-[(Z)-(3S,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxy)-3,5-dimethyl-hex-1-enyl]-[1,3]dioxan-4-yl}-propionic acid ethyl ester (475051-52-6)

Guidance literature:

Multi-step reaction with 6 steps

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

2: 80 percent / DIBALH / CH₂Cl₂ / 3 h / -78 °C

3: 90 percent / (COCl)2; DMSO; NEt₃ / CH₂Cl₂ / -78 - 0 °C

4: BH₃*THF / chiral borane from L-TsVal / -78 °C

5: 80 percent / P₂O₅ / CHCl₃ / 1 h / 20 °C

6: 85 percent / Bu₃SnH; Et₃B / toluene / 3 h / -78 °C

With 2,6-dimethylpyridine; borane-THF; oxalyl dichloride; triethyl borane; tri-n-butyl-tin hydride; phosphorus pentoxide; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; chiral borane from L-TsVal; In dichloromethane; chloroform; toluene; 3: Swern oxidation;

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

upstream raw materials:

ethyl (2R,3S,5S,6Z,8S,9S,10S)-2-bromo-9-(tert-butyldimethylsiloxy)-11-(tert-butyldiphenylsiloxy)-2,8,10-trimethyl-3,5-methylenedioxy-6-undecenoate

(3S,4Z,6S,7S,8S)-3,7-di-(tert-butyldimethylsiloxy)-9-(tert-butyldiphenylsiloxy)-6,8-dimethyl-4-nonenal

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

(Z)-(3S,6S,7S,8S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-9-(tert-butyl-diphenyl-silanyloxy)-6,8-dimethyl-non-4-en-1-ol

Downstream raw materials:

(2S,3S,5S,6Z,8S,9S,10S)-9-(tert-butyldimethylsiloxy)-11-(tert-butyldiphenylsiloxy)-2,8,10-trimethyl-3,5-methylenedioxy-6-undecenal

(2R,3S,4R)-4-{(4S,6S)-6-[(Z)-(3S,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxy)-3,5-dimethyl-hex-1-enyl]-[1,3]dioxan-4-yl}-3-hydroxy-2-methyl-pentanoic acid ethyl ester