(2S,3S,4R)-2-(2-((tert-butyldimethylsilyl)oxy)ethyl)-4-methyl-3-((triisopropylsilyl)oxy)cyclopentanone

Base Information

Chemical Name:(2S,3S,4R)-2-(2-((tert-butyldimethylsilyl)oxy)ethyl)-4-methyl-3-((triisopropylsilyl)oxy)cyclopentanone
CAS No.:1591271-05-4
Molecular Formula:C₂₃H₄₈O₃Si₂
Molecular Weight:428.803
Hs Code.:

Synonyms:(2S,3S,4R)-2-(2-((tert-butyldimethylsilyl)oxy)ethyl)-4-methyl-3-((triisopropylsilyl)oxy)cyclopentanone

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Chemical Property of (2S,3S,4R)-2-(2-((tert-butyldimethylsilyl)oxy)ethyl)-4-methyl-3-((triisopropylsilyl)oxy)cyclopentanone

Chemical Property:

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Technology Process of (2S,3S,4R)-2-(2-((tert-butyldimethylsilyl)oxy)ethyl)-4-methyl-3-((triisopropylsilyl)oxy)cyclopentanone

There total 1 articles about (2S,3S,4R)-2-(2-((tert-butyldimethylsilyl)oxy)ethyl)-4-methyl-3-((triisopropylsilyl)oxy)cyclopentanone 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:

: 80522-42-5
triisopropylsilyl trifluoromethanesulfonate

: 1591271-05-4
(2S,3S,4R)-2-(2-((tert-butyldimethylsilyl)oxy)ethyl)-4-methyl-3-((triisopropylsilyl)oxy)cyclopentanone

Guidance literature:: Multi-step reaction with 5 steps

1.1: 2,6-dimethylpyridine / dichloromethane / 14 h / 0 °C / Inert atmosphere

2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 1 h / Inert atmosphere; Reflux

3.1: lithium aluminium tetrahydride / tetrahydrofuran / 3.5 h / 0 °C / Inert atmosphere

4.1: 1H-imidazole / Inert atmosphere

4.2: Inert atmosphere

5.1: copper(l) iodide / diethyl ether / 1 h / -78 - 0 °C / Inert atmosphere

5.2: 1 h / -78 °C / Inert atmosphere

With 1H-imidazole; 2,6-dimethylpyridine; copper(l) iodide; lithium aluminium tetrahydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1002/ejoc.201301616

Reference yield: 50.0%

: 1591271-05-4
(2S,3S,4R)-2-(2-((tert-butyldimethylsilyl)oxy)ethyl)-4-methyl-3-((triisopropylsilyl)oxy)cyclopentanone

: (S)-1-(((3-bromo-2-methylbut-3-en-1-yl)oxy)methyl)-4-methoxybenzene

: 1591271-09-8
(1R,2S,3S,4R)-2-(2-((tert-butyldimethylsilyl)oxy)ethyl)-1-((R)-4-((4-methoxybenzyl)oxy)-3-methylbut-1-en-2-yl)-4-methyl-3-((triisopropylsilyl)oxy)cyclopentan-1-ol

: 1591271-10-1
(1S,2S,3S,4R)-2-(2-((tert-butyldimethylsilyl)oxy)ethyl)-1-((R)-4-((4-methoxybenzyl)oxy)-3-methylbut-1-en-2-yl)-4-methyl-3-((triisopropylsilyl)oxy)cyclopentan-1-ol

Guidance literature:: (S)-1-(((3-bromo-2-methylbut-3-en-1-yl)oxy)methyl)-4-methoxybenzene; With tert.-butyl lithium; In diethyl ether; pentane; at -78 - 20 ℃; for 0.583333h; Inert atmosphere;

(2S,3S,4R)-2-(2-((tert-butyldimethylsilyl)oxy)ethyl)-4-methyl-3-((triisopropylsilyl)oxy)cyclopentanone; In diethyl ether; pentane; at -78 ℃; for 5h; Inert atmosphere;
DOI:10.1002/ejoc.201301616

Reference yield:

: 1591271-05-4
(2S,3S,4R)-2-(2-((tert-butyldimethylsilyl)oxy)ethyl)-4-methyl-3-((triisopropylsilyl)oxy)cyclopentanone

: 1591271-15-6
triisopropyl(((4S,5R,6S,7S,8R)-4-((S)-1-((4-methoxybenzyl)oxy)propan-2-yl)-6-(2-((2-methoxypropan-2-yl)oxy)ethyl)-2,2,8-trimethyl-1,3-dioxaspiro[4.4]nonan-7-yl)oxy)silane

Guidance literature:: Multi-step reaction with 4 steps

1.1: tert.-butyl lithium / pentane; diethyl ether / 0.58 h / -78 - 20 °C / Inert atmosphere

1.2: 5 h / -78 °C / Inert atmosphere

2.1: pyridine; ozone; Sudan III / methanol; dichloromethane / -78 °C / Inert atmosphere

2.2: 12 h / 20 °C / Inert atmosphere

3.1: sodium tetrahydroborate / dichloromethane; ethanol / 24 h / 20 °C / Inert atmosphere

4.1: pyridinium p-toluenesulfonate / 24 h / 20 °C / Inert atmosphere

With pyridine; sodium tetrahydroborate; tert.-butyl lithium; pyridinium p-toluenesulfonate; ozone; Sudan III; In methanol; diethyl ether; ethanol; dichloromethane; pentane;
DOI:10.1002/ejoc.201301616