(2R,3R,4S,5Z,8S,9R,10R,11S,12S,Z)-9-(tert-butyldimethylsilyloxy)-11-(4-methoxybenzyloxy)-3-(methoxymethyloxy)-2,4,6,8,10,12-hexamethylhexadec-5-enal

Base Information

Chemical Name:(2R,3R,4S,5Z,8S,9R,10R,11S,12S,Z)-9-(tert-butyldimethylsilyloxy)-11-(4-methoxybenzyloxy)-3-(methoxymethyloxy)-2,4,6,8,10,12-hexamethylhexadec-5-enal
CAS No.:1334327-36-4
Molecular Formula:C₃₈H₆₈O₆Si
Molecular Weight:649.04
Hs Code.:

(2R,3R,4S,5Z,8S,9R,10R,11S,12S,Z)-9-(tert-butyldimethylsilyloxy)-11-(4-methoxybenzyloxy)-3-(methoxymethyloxy)-2,4,6,8,10,12-hexamethylhexadec-5-enal

Synonyms:(2R,3R,4S,5Z,8S,9R,10R,11S,12S,Z)-9-(tert-butyldimethylsilyloxy)-11-(4-methoxybenzyloxy)-3-(methoxymethyloxy)-2,4,6,8,10,12-hexamethylhexadec-5-enal

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Chemical Property of (2R,3R,4S,5Z,8S,9R,10R,11S,12S,Z)-9-(tert-butyldimethylsilyloxy)-11-(4-methoxybenzyloxy)-3-(methoxymethyloxy)-2,4,6,8,10,12-hexamethylhexadec-5-enal

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Technology Process of (2R,3R,4S,5Z,8S,9R,10R,11S,12S,Z)-9-(tert-butyldimethylsilyloxy)-11-(4-methoxybenzyloxy)-3-(methoxymethyloxy)-2,4,6,8,10,12-hexamethylhexadec-5-enal

There total 4 articles about (2R,3R,4S,5Z,8S,9R,10R,11S,12S,Z)-9-(tert-butyldimethylsilyloxy)-11-(4-methoxybenzyloxy)-3-(methoxymethyloxy)-2,4,6,8,10,12-hexamethylhexadec-5-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:

: 870075-19-7
(Z)-(2S,3R,4S,8S,9R,10R,11S,12S)-9-(tert-Butyl-dimethyl-silanyloxy)-11-(4-methoxy-benzyloxy)-3-methoxymethoxy-2,4,6,8,10,12-hexamethyl-hexadec-5-en-1-ol

: 1334327-36-4
(2R,3R,4S,5Z,8S,9R,10R,11S,12S,Z)-9-(tert-butyldimethylsilyloxy)-11-(4-methoxybenzyloxy)-3-(methoxymethyloxy)-2,4,6,8,10,12-hexamethylhexadec-5-enal

Guidance literature:: With sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine; In dichloromethane; at 0 ℃; for 1h; Inert atmosphere;
DOI:10.1016/j.bmc.2011.06.082

Reference yield:

: 870074-98-9
tert-Butyl-[(1S,2R,3S,4S)-1-((R)-2-iodo-1-methyl-ethyl)-3-(4-methoxy-benzyloxy)-2,4-dimethyl-octyloxy]-dimethyl-silane

: 1334327-36-4
(2R,3R,4S,5Z,8S,9R,10R,11S,12S,Z)-9-(tert-butyldimethylsilyloxy)-11-(4-methoxybenzyloxy)-3-(methoxymethyloxy)-2,4,6,8,10,12-hexamethylhexadec-5-enal

Guidance literature:: Multi-step reaction with 3 steps

1.1: tert.-butyl lithium; 9-methoxy-9-BBN / tetrahydrofuran; diethyl ether; hexane; pentane / 1 h / -78 - 20 °C / Inert atmosphere

1.2: 20 h / 20 °C / Inert atmosphere; Darkness

2.1: hydrogenchloride / ethanol / 0.33 h / 20 °C / Inert atmosphere

3.1: sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine / dichloromethane / 1 h / 0 °C / Inert atmosphere

With hydrogenchloride; tert.-butyl lithium; sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine; 9-methoxy-9-BBN; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; pentane; 1.2: Suzuki coupling / 3.1: Parikh-Doering oxidation;
DOI:10.1016/j.bmc.2011.06.082

Reference yield:

: 870075-18-6
1-[(Z)-(1S,2R,3R,4S,8S,9R,10S)-3,11-Bis-(tert-butyl-dimethyl-silanyloxy)-9-methoxymethoxy-2,4,6,8,10-pentamethyl-1-((S)-1-methyl-pentyl)-undec-6-enyloxymethyl]-4-methoxy-benzene

: 1334327-36-4
(2R,3R,4S,5Z,8S,9R,10R,11S,12S,Z)-9-(tert-butyldimethylsilyloxy)-11-(4-methoxybenzyloxy)-3-(methoxymethyloxy)-2,4,6,8,10,12-hexamethylhexadec-5-enal

Guidance literature:: Multi-step reaction with 2 steps

1: hydrogenchloride / ethanol / 0.33 h / 20 °C / Inert atmosphere

2: sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine / dichloromethane / 1 h / 0 °C / Inert atmosphere

With hydrogenchloride; sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine; In ethanol; dichloromethane; 2: Parikh-Doering oxidation;
DOI:10.1016/j.bmc.2011.06.082