(4R,5S,E)-methyl 4-(benzyloxy)-7-((tert-butyldimethylsilyl)oxy)-5-methylhept-2-enoate

Base Information

Chemical Name:(4R,5S,E)-methyl 4-(benzyloxy)-7-((tert-butyldimethylsilyl)oxy)-5-methylhept-2-enoate
CAS No.:1414917-21-7
Molecular Formula:C₂₂H₃₆O₄Si
Molecular Weight:392.611
Hs Code.:

Synonyms:(4R,5S,E)-methyl 4-(benzyloxy)-7-((tert-butyldimethylsilyl)oxy)-5-methylhept-2-enoate

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Chemical Property of (4R,5S,E)-methyl 4-(benzyloxy)-7-((tert-butyldimethylsilyl)oxy)-5-methylhept-2-enoate

Chemical Property:

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Technology Process of (4R,5S,E)-methyl 4-(benzyloxy)-7-((tert-butyldimethylsilyl)oxy)-5-methylhept-2-enoate

There total 5 articles about (4R,5S,E)-methyl 4-(benzyloxy)-7-((tert-butyldimethylsilyl)oxy)-5-methylhept-2-enoate 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: 90.0%

: 5927-18-4
trimethyl phosphonoacetate

: 1414917-72-8
C₁₉H₃₂O₃Si

: 1414917-21-7
(4R,5S,E)-methyl 4-(benzyloxy)-7-((tert-butyldimethylsilyl)oxy)-5-methylhept-2-enoate

Guidance literature:: With N-ethyl-N,N-diisopropylamine; lithium chloride; In acetonitrile; at 60 ℃; for 1.5h;
DOI:10.1021/jo302138z

Reference yield:

: 869384-94-1
(3S,4R,E)-4-(benzyloxy)-3-methyl-6-phenylhex-5-enenitrile

: 1414917-21-7
(4R,5S,E)-methyl 4-(benzyloxy)-7-((tert-butyldimethylsilyl)oxy)-5-methylhept-2-enoate

Guidance literature:: Multi-step reaction with 5 steps

1: diisobutylaluminium hydride / toluene / 25 h / -78 - -55 °C

2: sodium tetrahydroborate / methanol / 1 h / 0 - 20 °C

3: 1H-imidazole / N,N-dimethyl-formamide

4: ozone; triphenylphosphine / dichloromethane / 3 h / -78 - 20 °C

5: lithium chloride; N-ethyl-N,N-diisopropylamine / acetonitrile / 1.5 h / 60 °C

With 1H-imidazole; sodium tetrahydroborate; diisobutylaluminium hydride; ozone; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium chloride; In methanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1021/jo302138z

Reference yield:

: 1414917-20-6
(((3S,4R,E)-4-(benzyloxy)-3-methyl-6-phenylhex-5-en-1-yl)oxy)(tert-butyl)dimethylsilane

: 1414917-21-7
(4R,5S,E)-methyl 4-(benzyloxy)-7-((tert-butyldimethylsilyl)oxy)-5-methylhept-2-enoate

Guidance literature:: Multi-step reaction with 2 steps

1: ozone; triphenylphosphine / dichloromethane / 3 h / -78 - 20 °C

2: lithium chloride; N-ethyl-N,N-diisopropylamine / acetonitrile / 1.5 h / 60 °C

With ozone; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium chloride; In dichloromethane; acetonitrile;
DOI:10.1021/jo302138z