{(1S,4R)-3-[4'-benzyloxybut-(Z)-ylidene]-4-methoxymethoxy-2-methylenecyclopentyl}methanol

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Chemical Name:{(1S,4R)-3-[4'-benzyloxybut-(Z)-ylidene]-4-methoxymethoxy-2-methylenecyclopentyl}methanol
CAS No.:896110-49-9
Molecular Formula:C₂₀H₂₈O₄
Molecular Weight:332.44
Hs Code.:

Synonyms:{(1S,4R)-3-[4'-benzyloxybut-(Z)-ylidene]-4-methoxymethoxy-2-methylenecyclopentyl}methanol

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Chemical Property of {(1S,4R)-3-[4'-benzyloxybut-(Z)-ylidene]-4-methoxymethoxy-2-methylenecyclopentyl}methanol

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Technology Process of {(1S,4R)-3-[4'-benzyloxybut-(Z)-ylidene]-4-methoxymethoxy-2-methylenecyclopentyl}methanol

There total 11 articles about {(1S,4R)-3-[4'-benzyloxybut-(Z)-ylidene]-4-methoxymethoxy-2-methylenecyclopentyl}methanol 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: 88.0%

: 896110-70-6
{(1S,4R)-3-[4-Benzyloxy-but-(Z)-ylidene]-4-methoxymethoxy-2-methylene-cyclopentylmethoxy}-tert-butyl-diphenyl-silane

: 896110-49-9
{(1S,4R)-3-[4'-benzyloxybut-(Z)-ylidene]-4-methoxymethoxy-2-methylenecyclopentyl}methanol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 4h;
DOI:10.1016/j.tet.2005.11.096

Reference yield:

: 896110-43-3
(E)-(S)-6-(tert-butyldiphenylsilyloxy)-3-(tert-butyldiphenylsilyloxymethyl)hex-4-enal

: 896110-49-9
{(1S,4R)-3-[4'-benzyloxybut-(Z)-ylidene]-4-methoxymethoxy-2-methylenecyclopentyl}methanol

Guidance literature:: Multi-step reaction with 8 steps

1.1: n-BuLi / tetrahydrofuran; hexane / -78 - -40 °C

1.2: 87 percent / tetrahydrofuran; hexane / 1 h / -78 - -40 °C

2.1: 95 percent / MnO₂ / CH₂Cl₂ / 19 h

3.1: (R)-CBS; BH₃ / tetrahydrofuran / 1.25 h / -78 - -40 °C

4.1: 96 percent / ethyldiisopropylamine / CH₂Cl₂ / 8.5 h / 0 - 20 °C

5.1: O₃ / hexane / 0.25 h / -78 °C

5.2: PPh₃ / hexane; diethyl ether / -78 - 20 °C

6.1: BuLi / hexane; diethyl ether / 4 h / 0 °C

6.2: 85 percent / diethyl ether; hexane / 0 °C

7.1: 31 percent / N,N-bis-(benzylidene)ethylenediamine / Pd(OAc)2 / CH₂Cl₂ / 72 h / 60 °C

8.1: 88 percent / TBAF / tetrahydrofuran / 4 h / 20 °C

With manganese(IV) oxide; n-butyllithium; N,N'-bis(benzyliden)ethylendiamine; borane; tetrabutyl ammonium fluoride; ozone; N-ethyl-N,N-diisopropylamine; (R)-(+)-2-methyl-CBS-oxazaborolidine; palladium diacetate; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; 6.2: Wittig reaction;
DOI:10.1016/j.tet.2005.11.096

Reference yield:

: (2R,4R)-9-Benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-4-methoxymethoxy-non-5-ynal

: 896110-49-9
{(1S,4R)-3-[4'-benzyloxybut-(Z)-ylidene]-4-methoxymethoxy-2-methylenecyclopentyl}methanol

Guidance literature:: Multi-step reaction with 3 steps

1.1: BuLi / hexane; diethyl ether / 4 h / 0 °C

1.2: 85 percent / diethyl ether; hexane / 0 °C

2.1: 31 percent / N,N-bis-(benzylidene)ethylenediamine / Pd(OAc)2 / CH₂Cl₂ / 72 h / 60 °C

3.1: 88 percent / TBAF / tetrahydrofuran / 4 h / 20 °C

With n-butyllithium; N,N'-bis(benzyliden)ethylendiamine; tetrabutyl ammonium fluoride; palladium diacetate; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; 1.2: Wittig reaction;
DOI:10.1016/j.tet.2005.11.096