ethyl (2R,3S,4R,5S,6S)-2-bromo-7-(tert-butyldimethylsiloxy)-3-hydroxy-5-(4-methoxybenzyloxy)-2,4,6-trimethylheptanoate

Base Information

Chemical Name:ethyl (2R,3S,4R,5S,6S)-2-bromo-7-(tert-butyldimethylsiloxy)-3-hydroxy-5-(4-methoxybenzyloxy)-2,4,6-trimethylheptanoate
CAS No.:475143-06-7
Molecular Formula:C₂₆H₄₅BrO₆Si
Molecular Weight:561.629
Hs Code.:

Synonyms:ethyl (2R,3S,4R,5S,6S)-2-bromo-7-(tert-butyldimethylsiloxy)-3-hydroxy-5-(4-methoxybenzyloxy)-2,4,6-trimethylheptanoate

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Chemical Property of ethyl (2R,3S,4R,5S,6S)-2-bromo-7-(tert-butyldimethylsiloxy)-3-hydroxy-5-(4-methoxybenzyloxy)-2,4,6-trimethylheptanoate

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Technology Process of ethyl (2R,3S,4R,5S,6S)-2-bromo-7-(tert-butyldimethylsiloxy)-3-hydroxy-5-(4-methoxybenzyloxy)-2,4,6-trimethylheptanoate

There total 10 articles about ethyl (2R,3S,4R,5S,6S)-2-bromo-7-(tert-butyldimethylsiloxy)-3-hydroxy-5-(4-methoxybenzyloxy)-2,4,6-trimethylheptanoate 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: 65.0%

: 153645-08-0
2-bromo-1-ethoxy-2-methyl-1-trimethylsilyoxyethene

: 184292-01-1
(2R,3S,4S)-5-(tert-butyldimethylsiloxy)-3-(4-methoxybenzyloxy)-2,4-dimethylpentanal

: 475143-06-7
ethyl (2R,3S,4R,5S,6S)-2-bromo-7-(tert-butyldimethylsiloxy)-3-hydroxy-5-(4-methoxybenzyloxy)-2,4,6-trimethylheptanoate

Guidance literature:: With boron trifluoride diethyl etherate; In dichloromethane; at -78 ℃; for 1h;
DOI:10.1016/S0040-4039(02)01373-4 DOI:10.1021/jo034901c

Reference yield:

: 374896-36-3
ethyl (2R,3S,4S)-2-bromo-5-(tert-butyldimethylsiloxy)-3-hydroxy-2,4-dimethylpentanoate

: 475143-06-7
ethyl (2R,3S,4R,5S,6S)-2-bromo-7-(tert-butyldimethylsiloxy)-3-hydroxy-5-(4-methoxybenzyloxy)-2,4,6-trimethylheptanoate

Guidance literature:: Multi-step reaction with 4 steps

1: 80 percent / Mg; ethelene dibromide; Bu₃SnH / Et₃B / CH₂Cl₂; diethyl ether / 2 h / 0 °C

2: 60 percent / TfOH / diethyl ether / 20 h / 20 °C

3: 65 percent / DIBALH / CH₂Cl₂; toluene / 2 h / -78 °C

4: 65 percent / BF₃*OEt₂ / CH₂Cl₂ / 1 h / -78 °C

With trifluorormethanesulfonic acid; boron trifluoride diethyl etherate; tri-n-butyl-tin hydride; diisobutylaluminium hydride; magnesium; ethylene dibromide; triethyl borane; In diethyl ether; dichloromethane; toluene;
DOI:10.1021/jo034901c

Reference yield:

: 89238-99-3
O-(4-methoxybenzyl)-trichloroacetimidate

: 475143-06-7
ethyl (2R,3S,4R,5S,6S)-2-bromo-7-(tert-butyldimethylsiloxy)-3-hydroxy-5-(4-methoxybenzyloxy)-2,4,6-trimethylheptanoate

Guidance literature:: Multi-step reaction with 3 steps

1: 60 percent / TfOH / diethyl ether / 20 h / 20 °C

2: 65 percent / DIBALH / CH₂Cl₂; toluene / 2 h / -78 °C

3: 65 percent / BF₃*OEt₂ / CH₂Cl₂ / 1 h / -78 °C

With trifluorormethanesulfonic acid; boron trifluoride diethyl etherate; diisobutylaluminium hydride; In diethyl ether; dichloromethane; toluene;
DOI:10.1021/jo034901c