ethyl (2R,3S,5S,6Z,8S,9S,10S)-2-bromo-5,9-di-(tert-butyldimethylsiloxy)-11-(tert-butyldiphenylsiloxy)-3-methoxymethoxy-2,8,10-trimethyl-6-undecenoate

Base Information

Chemical Name:ethyl (2R,3S,5S,6Z,8S,9S,10S)-2-bromo-5,9-di-(tert-butyldimethylsiloxy)-11-(tert-butyldiphenylsiloxy)-3-methoxymethoxy-2,8,10-trimethyl-6-undecenoate
CAS No.:625109-88-8
Molecular Formula:C₄₆H₇₉BrO₇Si₃
Molecular Weight:908.29
Hs Code.:

ethyl (2R,3S,5S,6Z,8S,9S,10S)-2-bromo-5,9-di-(tert-butyldimethylsiloxy)-11-(tert-butyldiphenylsiloxy)-3-methoxymethoxy-2,8,10-trimethyl-6-undecenoate

Synonyms:ethyl (2R,3S,5S,6Z,8S,9S,10S)-2-bromo-5,9-di-(tert-butyldimethylsiloxy)-11-(tert-butyldiphenylsiloxy)-3-methoxymethoxy-2,8,10-trimethyl-6-undecenoate

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Chemical Property of ethyl (2R,3S,5S,6Z,8S,9S,10S)-2-bromo-5,9-di-(tert-butyldimethylsiloxy)-11-(tert-butyldiphenylsiloxy)-3-methoxymethoxy-2,8,10-trimethyl-6-undecenoate

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Technology Process of ethyl (2R,3S,5S,6Z,8S,9S,10S)-2-bromo-5,9-di-(tert-butyldimethylsiloxy)-11-(tert-butyldiphenylsiloxy)-3-methoxymethoxy-2,8,10-trimethyl-6-undecenoate

There total 6 articles about ethyl (2R,3S,5S,6Z,8S,9S,10S)-2-bromo-5,9-di-(tert-butyldimethylsiloxy)-11-(tert-butyldiphenylsiloxy)-3-methoxymethoxy-2,8,10-trimethyl-6-undecenoate 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: 75.0%

: 109-87-5
Dimethoxymethane

: ethyl (3S,5S,6Z,8S,9S,10S)-2-bromo-5,9-di-(tert-butyldimethylsiloxy)-11-(tert-butyldiphenylsiloxy)-3-hydroxy-2,8,10-trimethyl-6-undecenoate

: 625109-88-8
ethyl (2R,3S,5S,6Z,8S,9S,10S)-2-bromo-5,9-di-(tert-butyldimethylsiloxy)-11-(tert-butyldiphenylsiloxy)-3-methoxymethoxy-2,8,10-trimethyl-6-undecenoate

Guidance literature:: With phosphorus pentoxide; In chloroform; at 20 ℃; for 0.333333h;
DOI:10.1021/jo034901c

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 625109-88-8
ethyl (2R,3S,5S,6Z,8S,9S,10S)-2-bromo-5,9-di-(tert-butyldimethylsiloxy)-11-(tert-butyldiphenylsiloxy)-3-methoxymethoxy-2,8,10-trimethyl-6-undecenoate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 87 percent / 2,6-lutidine / 1 h / 20 °C

2.1: 80 percent / DIBALH / CH₂Cl₂ / 3 h / -78 °C

3.1: 93 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

4.1: BH₃*THF / CH₂Cl₂; tetrahydrofuran / 1 h / 0 - 20 °C

4.2: 86 percent / CH₂Cl₂; tetrahydrofuran / 16 h / -78 °C

5.1: 75 percent / P₂O₅ / CHCl₃ / 0.33 h / 20 °C

With 2,6-dimethylpyridine; borane-THF; oxalyl dichloride; phosphorus pentoxide; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; chloroform; 3.1: Swern oxidation;
DOI:10.1021/jo034901c

Reference yield:

: 475051-50-4
(3S,4Z,6S,7S,8S)-3,7-di-(tert-butyldimethylsiloxy)-9-(tert-butyldiphenylsiloxy)-6,8-dimethyl-4-nonenal

: 625109-88-8
ethyl (2R,3S,5S,6Z,8S,9S,10S)-2-bromo-5,9-di-(tert-butyldimethylsiloxy)-11-(tert-butyldiphenylsiloxy)-3-methoxymethoxy-2,8,10-trimethyl-6-undecenoate

Guidance literature:: Multi-step reaction with 2 steps

1.1: BH₃*THF / CH₂Cl₂; tetrahydrofuran / 1 h / 0 - 20 °C

1.2: 86 percent / CH₂Cl₂; tetrahydrofuran / 16 h / -78 °C

2.1: 75 percent / P₂O₅ / CHCl₃ / 0.33 h / 20 °C

With borane-THF; phosphorus pentoxide; In tetrahydrofuran; dichloromethane; chloroform;
DOI:10.1021/jo034901c