[(2R,3S,4S)-1-[2-Benzyloxymethoxy-eth-(Z)-ylidene]-2,4-dimethyl-3-(tetrahydro-pyran-2-yloxy)-hex-5-enyl]-trimethyl-silane

Base Information

Chemical Name:[(2R,3S,4S)-1-[2-Benzyloxymethoxy-eth-(Z)-ylidene]-2,4-dimethyl-3-(tetrahydro-pyran-2-yloxy)-hex-5-enyl]-trimethyl-silane
CAS No.:103590-67-6
Molecular Formula:C₂₆H₄₂O₄Si
Molecular Weight:446.703
Hs Code.:

Synonyms:[(2R,3S,4S)-1-[2-Benzyloxymethoxy-eth-(Z)-ylidene]-2,4-dimethyl-3-(tetrahydro-pyran-2-yloxy)-hex-5-enyl]-trimethyl-silane

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Chemical Property of [(2R,3S,4S)-1-[2-Benzyloxymethoxy-eth-(Z)-ylidene]-2,4-dimethyl-3-(tetrahydro-pyran-2-yloxy)-hex-5-enyl]-trimethyl-silane

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Technology Process of [(2R,3S,4S)-1-[2-Benzyloxymethoxy-eth-(Z)-ylidene]-2,4-dimethyl-3-(tetrahydro-pyran-2-yloxy)-hex-5-enyl]-trimethyl-silane

There total 8 articles about [(2R,3S,4S)-1-[2-Benzyloxymethoxy-eth-(Z)-ylidene]-2,4-dimethyl-3-(tetrahydro-pyran-2-yloxy)-hex-5-enyl]-trimethyl-silane 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: 94.0%

: 110-87-2
3,4-dihydro-2H-pyran

: 103563-37-7
(3S,4S,5R)-(Z)-8-<(benzyloxy)methoxy>-3,5-dimethyl-3-(trimethylsilyl)-1,6-octadien-4-ol

: 103590-67-6
[(2R,3S,4S)-1-[2-Benzyloxymethoxy-eth-(Z)-ylidene]-2,4-dimethyl-3-(tetrahydro-pyran-2-yloxy)-hex-5-enyl]-trimethyl-silane

Guidance literature:: With pyridinium p-toluenesulfonate; In dichloromethane; Ambient temperature;
DOI:10.1021/ja00277a028

Reference yield:

: 3587-60-8
Benzyloxymethyl chloride

: 103590-67-6
[(2R,3S,4S)-1-[2-Benzyloxymethoxy-eth-(Z)-ylidene]-2,4-dimethyl-3-(tetrahydro-pyran-2-yloxy)-hex-5-enyl]-trimethyl-silane

Guidance literature:: Multi-step reaction with 9 steps

1: NaH

2: EtMgBr

3: DIBAL, Br₂

4: 92 percent / n-BuLi / tetrahydrofuran; diethyl ether; hexane / 0.5 h

5: Et₃N / CH₂Cl₂ / 0.33 h / -45 °C

6: DIBAL, Et₃Al / CH₂Cl₂ / 2 h / -78 - -20 °C

7: (COCl)2, DMSO, Et₃N / CH₂Cl₂ / 0.5 h / -78 - 0 °C

8: CrCl₂ / tetrahydrofuran / 0 °C

9: 94 percent / PPTS / CH₂Cl₂ / Ambient temperature

With chromium dichloride; n-butyllithium; oxalyl dichloride; ethylmagnesium bromide; bromine; triethylaluminum; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane;
DOI:10.1021/ja00277a028

Reference yield:

: 103590-65-4
((E)-3-Benzyloxymethoxy-1-bromo-propenyl)-trimethyl-silane

: 103590-67-6
[(2R,3S,4S)-1-[2-Benzyloxymethoxy-eth-(Z)-ylidene]-2,4-dimethyl-3-(tetrahydro-pyran-2-yloxy)-hex-5-enyl]-trimethyl-silane

Guidance literature:: Multi-step reaction with 6 steps

1: 92 percent / n-BuLi / tetrahydrofuran; diethyl ether; hexane / 0.5 h

2: Et₃N / CH₂Cl₂ / 0.33 h / -45 °C

3: DIBAL, Et₃Al / CH₂Cl₂ / 2 h / -78 - -20 °C

4: (COCl)2, DMSO, Et₃N / CH₂Cl₂ / 0.5 h / -78 - 0 °C

5: CrCl₂ / tetrahydrofuran / 0 °C

6: 94 percent / PPTS / CH₂Cl₂ / Ambient temperature

With chromium dichloride; n-butyllithium; oxalyl dichloride; triethylaluminum; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane;
DOI:10.1021/ja00277a028