(4S,6S,9R,10S,11R)-12-(tert-butyldimethylsilyloxy)-10-(4-methoxybenzyloxy)-9,11-dimethyldodec-1-ene-4,6-diol

Base Information

• Chemical Name: (4S,6S,9R,10S,11R)-12-(tert-butyldimethylsilyloxy)-10-(4-methoxybenzyloxy)-9,11-dimethyldodec-1-ene-4,6-diol
• CAS No.: 1003890-58-1
• Molecular Formula: C₂₈H₅₀O₅Si
• Molecular Weight: 494.788

Synonyms:(4S,6S,9R,10S,11R)-12-(tert-butyldimethylsilyloxy)-10-(4-methoxybenzyloxy)-9,11-dimethyldodec-1-ene-4,6-diol

Chemical Property of (4S,6S,9R,10S,11R)-12-(tert-butyldimethylsilyloxy)-10-(4-methoxybenzyloxy)-9,11-dimethyldodec-1-ene-4,6-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,6S,9R,10S,11R)-12-(tert-butyldimethylsilyloxy)-10-(4-methoxybenzyloxy)-9,11-dimethyldodec-1-ene-4,6-diol

There total 5 articles about (4S,6S,9R,10S,11R)-12-(tert-butyldimethylsilyloxy)-10-(4-methoxybenzyloxy)-9,11-dimethyldodec-1-ene-4,6-diol 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:

(1S,6R,8R)-8-Vinyl-2,9,10-trioxa-1-phospha-bicyclo[4.3.1]dec-4-ene 1-oxide (887143-81-9) → (4S,6S,9R,10S,11R)-12-(tert-butyldimethylsilyloxy)-10-(4-methoxybenzyloxy)-9,11-dimethyldodec-1-ene-4,6-diol (1003890-58-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: Hoveyda-Grubbs catalyst second generation / 1,1-dichloroethane / 90 °C / Inert atmosphere

2.1: 2-nitrobenzenesulfonyl hydrazide; triethylamine / 1,2-dichloro-ethane / Inert atmosphere

3.1: formic acid; palladium diacetate; triethylamine / 1,2-dichloro-ethane / 40 °C / Inert atmosphere

3.2: Inert atmosphere

4.1: lithium aluminium tetrahydride / diethyl ether / Inert atmosphere

With lithium aluminium tetrahydride; formic acid; Hoveyda-Grubbs catalyst second generation; 2-nitrobenzenesulfonyl hydrazide; palladium diacetate; triethylamine; In diethyl ether; 1,1-dichloroethane; 1,2-dichloro-ethane;

DOI:10.1021/jo2003506

Reference yield:

(4R,6R)-2-Allyloxy-4,6-divinyl-[1,3,2]dioxaphosphinane 2-oxide (887343-98-8) → (4S,6S,9R,10S,11R)-12-(tert-butyldimethylsilyloxy)-10-(4-methoxybenzyloxy)-9,11-dimethyldodec-1-ene-4,6-diol (1003890-58-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane

2.1: Hoveyda-Grubbs catalyst second generation / 1,1-dichloroethane / 90 °C / Inert atmosphere

3.1: 2-nitrobenzenesulfonyl hydrazide; triethylamine / 1,2-dichloro-ethane / Inert atmosphere

4.1: formic acid; palladium diacetate; triethylamine / 1,2-dichloro-ethane / 40 °C / Inert atmosphere

4.2: Inert atmosphere

5.1: lithium aluminium tetrahydride / diethyl ether / Inert atmosphere

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; lithium aluminium tetrahydride; formic acid; Hoveyda-Grubbs catalyst second generation; 2-nitrobenzenesulfonyl hydrazide; palladium diacetate; triethylamine; In diethyl ether; 1,1-dichloroethane; dichloromethane; 1,2-dichloro-ethane;

DOI:10.1021/jo2003506

Reference yield:

(1R,6R,8S)-8-((3R,4S,5R)-6-((tert-butyldimethylsilyl)oxy)-4-((4-methoxybenzyl)oxy)-3,5-dimethylhexyl)-2,9,10-trioxa-1-phosphabicyclo[4.3.1]dec-4-ene 1-oxide (1003890-41-2) → (4S,6S,9R,10S,11R)-12-(tert-butyldimethylsilyloxy)-10-(4-methoxybenzyloxy)-9,11-dimethyldodec-1-ene-4,6-diol (1003890-58-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: formic acid; palladium diacetate; triethylamine / 1,2-dichloro-ethane / 40 °C / Inert atmosphere

1.2: Inert atmosphere

2.1: lithium aluminium tetrahydride / diethyl ether / Inert atmosphere

With lithium aluminium tetrahydride; formic acid; palladium diacetate; triethylamine; In diethyl ether; 1,2-dichloro-ethane;

DOI:10.1021/jo2003506

upstream raw materials:

(1S,6R,8R)-8-Vinyl-2,9,10-trioxa-1-phospha-bicyclo[4.3.1]dec-4-ene 1-oxide

(4R,6R)-2-Allyloxy-4,6-divinyl-[1,3,2]dioxaphosphinane 2-oxide

(1R,6R,8S)-8-((3R,4S,5R)-6-((tert-butyldimethylsilyl)oxy)-4-((4-methoxybenzyl)oxy)-3,5-dimethylhexyl)-2,9,10-trioxa-1-phosphabicyclo[4.3.1]dec-4-ene 1-oxide

Downstream raw materials:

((2R,3S,4R)-6-((4S,6S)-6-allyl-2,2-dimethyl-1,3-dioxan-4-yl)-3-(4-methoxybenzyloxy)-2,4-dimethylhexyloxy)(tert-butyl)dimethylsilane

C₃₀H₅₂O₆Si

C₃₅H₆₂O₆Si

1-((4R,6S)-6-((3R,4S,5R)-6-(tert-butyldimethylsilyloxy)-4-(4-methoxybenzyloxy)-3,5-dimethylhexyl)-2,2-dimethyl-1,3-dioxan-4-yl)-5-methylhex-5-en-2-one

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