ethyl (2E,4R,5S,6R,17S)-17-[[tert-butyl(diphenyl)silyl]oxy]-4,6-isopropylidenedioxy-5-[(2-methoxyethoxy)methoxy]-2-octadecenoate

Base Information

Chemical Name:ethyl (2E,4R,5S,6R,17S)-17-[[tert-butyl(diphenyl)silyl]oxy]-4,6-isopropylidenedioxy-5-[(2-methoxyethoxy)methoxy]-2-octadecenoate
CAS No.:288607-99-8
Molecular Formula:C₄₃H₆₈O₈Si
Molecular Weight:741.094
Hs Code.:

Synonyms:ethyl (2E,4R,5S,6R,17S)-17-[[tert-butyl(diphenyl)silyl]oxy]-4,6-isopropylidenedioxy-5-[(2-methoxyethoxy)methoxy]-2-octadecenoate

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Chemical Property of ethyl (2E,4R,5S,6R,17S)-17-[[tert-butyl(diphenyl)silyl]oxy]-4,6-isopropylidenedioxy-5-[(2-methoxyethoxy)methoxy]-2-octadecenoate

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Technology Process of ethyl (2E,4R,5S,6R,17S)-17-[[tert-butyl(diphenyl)silyl]oxy]-4,6-isopropylidenedioxy-5-[(2-methoxyethoxy)methoxy]-2-octadecenoate

There total 3 articles about ethyl (2E,4R,5S,6R,17S)-17-[[tert-butyl(diphenyl)silyl]oxy]-4,6-isopropylidenedioxy-5-[(2-methoxyethoxy)methoxy]-2-octadecenoate 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: 91.0%

: 867-13-0
diethoxyphosphoryl-acetic acid ethyl ester

: (4S,5S,6R)-6-[(S)-11-(tert-Butyl-diphenyl-silanyloxy)-dodecyl]-5-(2-methoxy-ethoxymethoxy)-2,2-dimethyl-[1,3]dioxane-4-carbaldehyde

: 288607-99-8
ethyl (2E,4R,5S,6R,17S)-17-[[tert-butyl(diphenyl)silyl]oxy]-4,6-isopropylidenedioxy-5-[(2-methoxyethoxy)methoxy]-2-octadecenoate

Guidance literature:: diethoxyphosphoryl-acetic acid ethyl ester; With n-butyllithium; In hexane; dichloromethane; at 0 ℃; for 0.333333h;

(4S,5S,6R)-6-[(S)-11-(tert-Butyl-diphenyl-silanyloxy)-dodecyl]-5-(2-methoxy-ethoxymethoxy)-2,2-dimethyl-[1,3]dioxane-4-carbaldehyde; In hexane; dichloromethane; at 0 ℃; for 0.333333h;
DOI:10.1016/S0040-4020(00)00337-9

Reference yield:

: 288607-98-7
(2R,3S,4R,15S)-15-[[tert-butyl(diphenyl)silyl]oxy]-2,4-isopropylidenedioxy-3-[(2-methoxyethoxy)methoxy]-1-hexadecanol

: 288607-99-8
ethyl (2E,4R,5S,6R,17S)-17-[[tert-butyl(diphenyl)silyl]oxy]-4,6-isopropylidenedioxy-5-[(2-methoxyethoxy)methoxy]-2-octadecenoate

Guidance literature:: Multi-step reaction with 2 steps

1.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -50 - 20 °C

2.1: n-BuLi / CH₂Cl₂; hexane / 0.33 h / 0 °C

2.2: 91 percent / CH₂Cl₂; hexane / 0.33 h / 0 °C

With n-butyllithium; oxalyl dichloride; dimethyl sulfoxide; triethylamine; In hexane; dichloromethane; 1.1: Swern oxidation / 2.1: depronoation / 2.2: Wittig reaction;
DOI:10.1016/S0040-4020(00)00337-9

Reference yield:

: (2R,3S,4RS,15S)-15-[[tert-butyl(diphenyl)silyl]oxy]-2,4-isopropylidenedioxy-3-[(2-methoxyethoxy)methoxy]hexadecyl pivalate

: 288607-99-8
ethyl (2E,4R,5S,6R,17S)-17-[[tert-butyl(diphenyl)silyl]oxy]-4,6-isopropylidenedioxy-5-[(2-methoxyethoxy)methoxy]-2-octadecenoate

Guidance literature:: Multi-step reaction with 3 steps

1.1: 77 percent / DIBAL-H / CH₂Cl₂; toluene / 0.25 h / -78 °C

2.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -50 - 20 °C

3.1: n-BuLi / CH₂Cl₂; hexane / 0.33 h / 0 °C

3.2: 91 percent / CH₂Cl₂; hexane / 0.33 h / 0 °C

With n-butyllithium; oxalyl dichloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In hexane; dichloromethane; toluene; 1.1: Reduction / 2.1: Swern oxidation / 3.1: depronoation / 3.2: Wittig reaction;
DOI:10.1016/S0040-4020(00)00337-9