(+)-(4S,5S,6S,7S,8S,9S,10S)-7,9,11-tris(benzyloxy)-4,6,8,10-tetramethyl-5-(triethylsilyloxy)undecanal

Base Information

• Chemical Name: (+)-(4S,5S,6S,7S,8S,9S,10S)-7,9,11-tris(benzyloxy)-4,6,8,10-tetramethyl-5-(triethylsilyloxy)undecanal
• CAS No.: 1333040-78-0
• Molecular Formula: C₄₂H₆₂O₅Si
• Molecular Weight: 675.037

Synonyms:(+)-(4S,5S,6S,7S,8S,9S,10S)-7,9,11-tris(benzyloxy)-4,6,8,10-tetramethyl-5-(triethylsilyloxy)undecanal

Chemical Property of (+)-(4S,5S,6S,7S,8S,9S,10S)-7,9,11-tris(benzyloxy)-4,6,8,10-tetramethyl-5-(triethylsilyloxy)undecanal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-(4S,5S,6S,7S,8S,9S,10S)-7,9,11-tris(benzyloxy)-4,6,8,10-tetramethyl-5-(triethylsilyloxy)undecanal

There total 18 articles about (+)-(4S,5S,6S,7S,8S,9S,10S)-7,9,11-tris(benzyloxy)-4,6,8,10-tetramethyl-5-(triethylsilyloxy)undecanal 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: 92.0%

(+)-(4S,5S,6S,7S,8S,9S,10S)-7,9,11-tris(benzyloxy)-4,6,8,10-tetramethyl-5-(triethylsilyloxy)undecan-1-ol (1333041-67-0) → (+)-(4S,5S,6S,7S,8S,9S,10S)-7,9,11-tris(benzyloxy)-4,6,8,10-tetramethyl-5-(triethylsilyloxy)undecanal (1333040-78-0)

Guidance literature:

(+)-(4S,5S,6S,7S,8S,9S,10S)-7,9,11-tris(benzyloxy)-4,6,8,10-tetramethyl-5-(triethylsilyloxy)undecan-1-ol; With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -78 ℃; for 0.5h; Inert atmosphere;

With triethylamine; In dichloromethane; at -78 ℃; for 1h; Inert atmosphere;

DOI:10.1021/jo2013884

Reference yield:

(2S,3S,4S)-3,5-bis(benzyloxy)-2,4-dimethylpentanal (1096706-74-9) → (+)-(4S,5S,6S,7S,8S,9S,10S)-7,9,11-tris(benzyloxy)-4,6,8,10-tetramethyl-5-(triethylsilyloxy)undecanal (1333040-78-0)

Guidance literature:

Multi-step reaction with 14 steps

1.1: titanium tetrachloride / dichloromethane / 78 °C / Inert atmosphere

2.1: di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine / dichloromethane / -78 °C / Inert atmosphere

2.2: -78 °C / Inert atmosphere

3.1: trifluorormethanesulfonic acid / dichloromethane; cyclohexane / 0 °C

4.1: diisobutylaluminium hydride / hexanes; dichloromethane / 1 h / -40 °C / Inert atmosphere

4.2: -40 °C

5.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

5.2: 1 h / -78 °C / Inert atmosphere

6.1: boron trifluoride diethyl etherate / dichloromethane / 1 h / -78 °C / Inert atmosphere

7.1: di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine / dichloromethane / 1.5 h / -78 °C / Inert atmosphere

7.2: -78 °C / Inert atmosphere

8.1: 2,6-dimethylpyridine / dichloromethane / 1.5 h / 0 °C / Inert atmosphere

9.1: diisobutylaluminium hydride / hexanes; dichloromethane / 1 h / -40 °C / Inert atmosphere

9.2: -40 °C

10.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

10.2: 1 h / -78 °C / Inert atmosphere

11.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride / acetonitrile / 0.5 h / 0 - 20 °C / Inert atmosphere

11.2: 4 h / 0 °C / Inert atmosphere

12.1: palladium 10% on activated carbon; hydrogen / methanol / 20 °C

13.1: diisobutylaluminium hydride / hexanes; dichloromethane / 1 h / -40 °C / Inert atmosphere

13.2: -40 °C

14.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

14.2: 1 h / -78 °C / Inert atmosphere

With 2,6-dimethylpyridine; oxalyl dichloride; trifluorormethanesulfonic acid; di-n-butylboryl trifluoromethanesulfonate; palladium 10% on activated carbon; boron trifluoride diethyl etherate; hydrogen; titanium tetrachloride; diisobutylaluminium hydride; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; lithium chloride; In methanol; hexanes; dichloromethane; cyclohexane; acetonitrile; 1.1: Mukaiyama reaction / 5.1: Swern oxidation / 5.2: Swern oxidation / 6.1: Mukaiyama reaction / 10.1: Swern oxidation / 10.2: Swern oxidation / 11.2: Horner-Wadsworth-Emmons olefination / 14.1: Swern oxidation / 14.2: Swern oxidation;

DOI:10.1021/jo2013884

Reference yield:

methyl (2S,3S,4S)-3,5-bis(benzyloxy)-2,4-dimethylpentanoate (1096707-44-6) → (+)-(4S,5S,6S,7S,8S,9S,10S)-7,9,11-tris(benzyloxy)-4,6,8,10-tetramethyl-5-(triethylsilyloxy)undecanal (1333040-78-0)

Guidance literature:

Multi-step reaction with 16 steps

1.1: diisobutylaluminium hydride / dichloromethane / -40 °C / Inert atmosphere

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / -78 °C / Inert atmosphere

2.2: -78 °C / Inert atmosphere

3.1: titanium tetrachloride / dichloromethane / 78 °C / Inert atmosphere

4.1: di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine / dichloromethane / -78 °C / Inert atmosphere

4.2: -78 °C / Inert atmosphere

5.1: trifluorormethanesulfonic acid / dichloromethane; cyclohexane / 0 °C

6.1: diisobutylaluminium hydride / hexanes; dichloromethane / 1 h / -40 °C / Inert atmosphere

6.2: -40 °C

7.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

7.2: 1 h / -78 °C / Inert atmosphere

8.1: boron trifluoride diethyl etherate / dichloromethane / 1 h / -78 °C / Inert atmosphere

9.1: di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine / dichloromethane / 1.5 h / -78 °C / Inert atmosphere

9.2: -78 °C / Inert atmosphere

10.1: 2,6-dimethylpyridine / dichloromethane / 1.5 h / 0 °C / Inert atmosphere

11.1: diisobutylaluminium hydride / hexanes; dichloromethane / 1 h / -40 °C / Inert atmosphere

11.2: -40 °C

12.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

12.2: 1 h / -78 °C / Inert atmosphere

13.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride / acetonitrile / 0.5 h / 0 - 20 °C / Inert atmosphere

13.2: 4 h / 0 °C / Inert atmosphere

14.1: palladium 10% on activated carbon; hydrogen / methanol / 20 °C

15.1: diisobutylaluminium hydride / hexanes; dichloromethane / 1 h / -40 °C / Inert atmosphere

15.2: -40 °C

16.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

16.2: 1 h / -78 °C / Inert atmosphere

With 2,6-dimethylpyridine; oxalyl dichloride; trifluorormethanesulfonic acid; di-n-butylboryl trifluoromethanesulfonate; palladium 10% on activated carbon; boron trifluoride diethyl etherate; hydrogen; titanium tetrachloride; diisobutylaluminium hydride; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; lithium chloride; In methanol; hexanes; dichloromethane; cyclohexane; acetonitrile; 2.1: Swern oxidation / 2.2: Swern oxidation / 3.1: Mukaiyama reaction / 7.1: Swern oxidation / 7.2: Swern oxidation / 8.1: Mukaiyama reaction / 12.1: Swern oxidation / 12.2: Swern oxidation / 13.2: Horner-Wadsworth-Emmons olefination / 16.1: Swern oxidation / 16.2: Swern oxidation;

DOI:10.1021/jo2013884

upstream raw materials:

(2S,3S,4S)-3,5-bis(benzyloxy)-2,4-dimethylpentanal

methyl (2S,3S,4S)-3,5-bis(benzyloxy)-2,4-dimethylpentanoate

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

(-)-(2R,3R,4R,5S,6S)-3,5,7-tris(benzyloxy)-2,4,6-trimethylheptan-1-ol

Downstream raw materials:

(+)-methyl 2-bromo-2-((2S,5S,6S)-5-methyl-6-((2S,3S,4S,5S,6S)-3,5,7-tris(benzyloxy)-4,6-dimethylheptan-2-yl)tetrahydro-2H-pyran-2-yl)propanoate

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