(1R,3R,4S)-3-(tert-butyldimethylsilyloxy)-1-((S)-5-(4-methoxybenzyloxy)-4-pent-1-en-2-yl)-4-(2-hydroxyethyl)-2,2-dimethylcyclobutanol

Base Information

Chemical Name:(1R,3R,4S)-3-(tert-butyldimethylsilyloxy)-1-((S)-5-(4-methoxybenzyloxy)-4-pent-1-en-2-yl)-4-(2-hydroxyethyl)-2,2-dimethylcyclobutanol
CAS No.:952092-41-0
Molecular Formula:C₂₈H₄₈O₅Si
Molecular Weight:492.772
Hs Code.:

Synonyms:(1R,3R,4S)-3-(tert-butyldimethylsilyloxy)-1-((S)-5-(4-methoxybenzyloxy)-4-pent-1-en-2-yl)-4-(2-hydroxyethyl)-2,2-dimethylcyclobutanol

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Chemical Property of (1R,3R,4S)-3-(tert-butyldimethylsilyloxy)-1-((S)-5-(4-methoxybenzyloxy)-4-pent-1-en-2-yl)-4-(2-hydroxyethyl)-2,2-dimethylcyclobutanol

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Technology Process of (1R,3R,4S)-3-(tert-butyldimethylsilyloxy)-1-((S)-5-(4-methoxybenzyloxy)-4-pent-1-en-2-yl)-4-(2-hydroxyethyl)-2,2-dimethylcyclobutanol

There total 4 articles about (1R,3R,4S)-3-(tert-butyldimethylsilyloxy)-1-((S)-5-(4-methoxybenzyloxy)-4-pent-1-en-2-yl)-4-(2-hydroxyethyl)-2,2-dimethylcyclobutanol 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: 60.0%

: 895532-65-7
(1R,3R,4S)-3-(tert-butyldimethylsilyloxy)-1-((S)-5-(4-methoxybenzyloxy)-4-methylpent-1-en-2-yl)-4-(2-(methoxymethoxy)ethyl)-2,2-dimethylcyclobutanol

: 952092-41-0
(1R,3R,4S)-3-(tert-butyldimethylsilyloxy)-1-((S)-5-(4-methoxybenzyloxy)-4-pent-1-en-2-yl)-4-(2-hydroxyethyl)-2,2-dimethylcyclobutanol

Guidance literature:: With pyridinium p-toluenesulfonate; In tert-butyl alcohol; at 83 ℃; for 10h;
DOI:10.1021/jo070862j

Reference yield:

: 895532-57-7
(1R,3R,4R)-1-(tert-butyldimethylsilyloxy)-3-benzyloxy-2,2-dimethyl-4-(2-methoxymethoxyethyl)cyclobutane

: 952092-41-0
(1R,3R,4S)-3-(tert-butyldimethylsilyloxy)-1-((S)-5-(4-methoxybenzyloxy)-4-pent-1-en-2-yl)-4-(2-hydroxyethyl)-2,2-dimethylcyclobutanol

Guidance literature:: Multi-step reaction with 4 steps

1.1: 100 percent / hydrogen / Pd/C / tetrahydrofuran / 24 h / 31029.7 Torr

2.1: 100 percent / N-methylmorpholine N-oxide monohydrate; tetrapropylammonium perruthenate; molecular sieves 4 Angstroem / acetonitrile; CH₂Cl₂ / 0.5 h

3.1: tert-butyllithium / tetrahydrofuran; pentane / 0.25 h / -78 °C

3.2: 71 percent / tetrahydrofuran; pentane / 3 h / -78 °C

4.1: 60 percent / pyridinium p-toluenesulfonate / 2-methyl-propan-2-ol / 10 h / 83 °C

With tetrapropylammonium perruthennate; 4 A molecular sieve; hydrogen; tert.-butyl lithium; pyridinium p-toluenesulfonate; 4-methylmorpholine N-oxide; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; acetonitrile; tert-butyl alcohol; pentane;
DOI:10.1021/jo070862j

Reference yield:

: 895532-62-4
(1R,3R,4R)-3-(tert-butyldimethylsilyloxy)-4-[2-(methoxymethoxy)ethyl]-2,2-dimethylcyclobutanol

: 952092-41-0
(1R,3R,4S)-3-(tert-butyldimethylsilyloxy)-1-((S)-5-(4-methoxybenzyloxy)-4-pent-1-en-2-yl)-4-(2-hydroxyethyl)-2,2-dimethylcyclobutanol

Guidance literature:: Multi-step reaction with 3 steps

1.1: 100 percent / N-methylmorpholine N-oxide monohydrate; tetrapropylammonium perruthenate; molecular sieves 4 Angstroem / acetonitrile; CH₂Cl₂ / 0.5 h

2.1: tert-butyllithium / tetrahydrofuran; pentane / 0.25 h / -78 °C

2.2: 71 percent / tetrahydrofuran; pentane / 3 h / -78 °C

3.1: 60 percent / pyridinium p-toluenesulfonate / 2-methyl-propan-2-ol / 10 h / 83 °C

With tetrapropylammonium perruthennate; 4 A molecular sieve; tert.-butyl lithium; pyridinium p-toluenesulfonate; 4-methylmorpholine N-oxide; In tetrahydrofuran; dichloromethane; acetonitrile; tert-butyl alcohol; pentane;
DOI:10.1021/jo070862j