methyl-(6S)-6-(3-(t-butyldimethylsilyloxy)-2-((t-butyldimethylsilyloxy)methyl)-prop-1-en-1-yl)-2-((diethoxyphosphoryl)-oxy)-1-cyclohexenecarboxylate

Base Information

Chemical Name:methyl-(6S)-6-(3-(t-butyldimethylsilyloxy)-2-((t-butyldimethylsilyloxy)methyl)-prop-1-en-1-yl)-2-((diethoxyphosphoryl)-oxy)-1-cyclohexenecarboxylate
CAS No.:443646-82-0
Molecular Formula:C₂₈H₅₅O₈PSi₂
Molecular Weight:606.885
Hs Code.:

methyl-(6S)-6-(3-(t-butyldimethylsilyloxy)-2-((t-butyldimethylsilyloxy)methyl)-prop-1-en-1-yl)-2-((diethoxyphosphoryl)-oxy)-1-cyclohexenecarboxylate

Synonyms:methyl-(6S)-6-(3-(t-butyldimethylsilyloxy)-2-((t-butyldimethylsilyloxy)methyl)-prop-1-en-1-yl)-2-((diethoxyphosphoryl)-oxy)-1-cyclohexenecarboxylate

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Chemical Property of methyl-(6S)-6-(3-(t-butyldimethylsilyloxy)-2-((t-butyldimethylsilyloxy)methyl)-prop-1-en-1-yl)-2-((diethoxyphosphoryl)-oxy)-1-cyclohexenecarboxylate

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Technology Process of methyl-(6S)-6-(3-(t-butyldimethylsilyloxy)-2-((t-butyldimethylsilyloxy)methyl)-prop-1-en-1-yl)-2-((diethoxyphosphoryl)-oxy)-1-cyclohexenecarboxylate

There total 3 articles about methyl-(6S)-6-(3-(t-butyldimethylsilyloxy)-2-((t-butyldimethylsilyloxy)methyl)-prop-1-en-1-yl)-2-((diethoxyphosphoryl)-oxy)-1-cyclohexenecarboxylate 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: 77.0%

: 814-49-3
diethyl chlorophosphate

: 6-[3-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-propenyl]-2-hydroxy-cyclohex-1-enecarboxylic acid methyl ester

: 443646-82-0
methyl-(6S)-6-(3-(t-butyldimethylsilyloxy)-2-((t-butyldimethylsilyloxy)methyl)-prop-1-en-1-yl)-2-((diethoxyphosphoryl)-oxy)-1-cyclohexenecarboxylate

Guidance literature:: 6-[3-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-propenyl]-2-hydroxy-cyclohex-1-enecarboxylic acid methyl ester; With sodium hydride; In tetrahydrofuran; at 20 ℃; for 0.333333h;

diethyl chlorophosphate; In tetrahydrofuran; at 0 - 20 ℃; for 4h;
DOI:10.1007/s706-002-8242-9

Reference yield:

: 116700-80-2
1-bromo-(3-tert-butyldimethylsilyloxy)-2-<(tert-butyldimethylsilyloxy)methyl>-1-propene

: 443646-82-0
methyl-(6S)-6-(3-(t-butyldimethylsilyloxy)-2-((t-butyldimethylsilyloxy)methyl)-prop-1-en-1-yl)-2-((diethoxyphosphoryl)-oxy)-1-cyclohexenecarboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: t-BuLi / diethyl ether; pentane / 2 h / -78 °C

1.2: lithium 2-thienyl-cyanocuprate / diethyl ether; pentane; tetrahydrofuran / 1 h / -78 °C

1.3: 82 percent / diethyl ether; pentane; tetrahydrofuran / 2 h / -78 °C

2.1: 93 percent / Et₃N / methanol / 15 h / 115 °C / 2850.23 Torr

3.1: NaH / tetrahydrofuran / 0.33 h / 20 °C

3.2: 77 percent / tetrahydrofuran / 4 h / 0 - 20 °C

With tert.-butyl lithium; sodium hydride; triethylamine; In tetrahydrofuran; methanol; diethyl ether; pentane;
DOI:10.1007/s706-002-8242-9

Reference yield:

: (S)-6-[3-(tert-Butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-propenyl]-2-hydroxy-cyclohex-1-enecarboxylic acid (1R,2R,3S,4S)-3-[benzenesulfonyl-(3,5-dimethyl-phenyl)-amino]-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester

: 443646-82-0
methyl-(6S)-6-(3-(t-butyldimethylsilyloxy)-2-((t-butyldimethylsilyloxy)methyl)-prop-1-en-1-yl)-2-((diethoxyphosphoryl)-oxy)-1-cyclohexenecarboxylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: 93 percent / Et₃N / methanol / 15 h / 115 °C / 2850.23 Torr

2.1: NaH / tetrahydrofuran / 0.33 h / 20 °C

2.2: 77 percent / tetrahydrofuran / 4 h / 0 - 20 °C

With sodium hydride; triethylamine; In tetrahydrofuran; methanol;
DOI:10.1007/s706-002-8242-9