(E)-(2S,4R,6R)-2-methoxy-2-((E)-3-methyl-5-phenylpent-3-en-1-yl)-6-((E)-2-methylhexa-2,5-dien-1-yl)tetrahydro-2H-pyran-4-yl 3-(2-((tert-butyldimethylsilyl)oxy)ethyl)hexa-2,5-dienoate

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Chemical Name:(E)-(2S,4R,6R)-2-methoxy-2-((E)-3-methyl-5-phenylpent-3-en-1-yl)-6-((E)-2-methylhexa-2,5-dien-1-yl)tetrahydro-2H-pyran-4-yl 3-(2-((tert-butyldimethylsilyl)oxy)ethyl)hexa-2,5-dienoate
CAS No.:1394247-89-2
Molecular Formula:C₃₉H₆₀O₅Si
Molecular Weight:636.988
Hs Code.:

(E)-(2S,4R,6R)-2-methoxy-2-((E)-3-methyl-5-phenylpent-3-en-1-yl)-6-((E)-2-methylhexa-2,5-dien-1-yl)tetrahydro-2H-pyran-4-yl 3-(2-((tert-butyldimethylsilyl)oxy)ethyl)hexa-2,5-dienoate

Synonyms:(E)-(2S,4R,6R)-2-methoxy-2-((E)-3-methyl-5-phenylpent-3-en-1-yl)-6-((E)-2-methylhexa-2,5-dien-1-yl)tetrahydro-2H-pyran-4-yl 3-(2-((tert-butyldimethylsilyl)oxy)ethyl)hexa-2,5-dienoate

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Chemical Property of (E)-(2S,4R,6R)-2-methoxy-2-((E)-3-methyl-5-phenylpent-3-en-1-yl)-6-((E)-2-methylhexa-2,5-dien-1-yl)tetrahydro-2H-pyran-4-yl 3-(2-((tert-butyldimethylsilyl)oxy)ethyl)hexa-2,5-dienoate

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Technology Process of (E)-(2S,4R,6R)-2-methoxy-2-((E)-3-methyl-5-phenylpent-3-en-1-yl)-6-((E)-2-methylhexa-2,5-dien-1-yl)tetrahydro-2H-pyran-4-yl 3-(2-((tert-butyldimethylsilyl)oxy)ethyl)hexa-2,5-dienoate

There total 7 articles about (E)-(2S,4R,6R)-2-methoxy-2-((E)-3-methyl-5-phenylpent-3-en-1-yl)-6-((E)-2-methylhexa-2,5-dien-1-yl)tetrahydro-2H-pyran-4-yl 3-(2-((tert-butyldimethylsilyl)oxy)ethyl)hexa-2,5-dienoate 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: 81.0%

: 1394247-82-5
(Z)-(2S,4R,6R)-6-((E)-3-iodo-2-methylallyl)-2-methoxy-2-((E)-3-methyl-5-phenylpent-3-en-1-yl)tetrahydro-2H-pyran-4-yl 5-((tert-butyldimethylsilyl)oxy)-3-iodopent-2-enoate

: 24850-33-7
allyltributylstanane

: 1394247-89-2
(E)-(2S,4R,6R)-2-methoxy-2-((E)-3-methyl-5-phenylpent-3-en-1-yl)-6-((E)-2-methylhexa-2,5-dien-1-yl)tetrahydro-2H-pyran-4-yl 3-(2-((tert-butyldimethylsilyl)oxy)ethyl)hexa-2,5-dienoate

Guidance literature:: With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In N,N-dimethyl-formamide; benzene; at 45 - 50 ℃; for 6h;
DOI:10.1021/ol302219x

Reference yield:

: 1394247-78-9
(2S,4R,6R)-6-((E)-3-iodo-2-methylallyl)-2-methoxy-2-((E)-3-methyl-5-phenylpent-3-en-1-yl)tetrahydro-2H-pyran-4-ol

: 1394247-89-2
(E)-(2S,4R,6R)-2-methoxy-2-((E)-3-methyl-5-phenylpent-3-en-1-yl)-6-((E)-2-methylhexa-2,5-dien-1-yl)tetrahydro-2H-pyran-4-yl 3-(2-((tert-butyldimethylsilyl)oxy)ethyl)hexa-2,5-dienoate

Guidance literature:: Multi-step reaction with 2 steps

1.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / toluene / 2 h / 0 °C

1.2: 0 °C

2.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide; benzene / 6 h / 45 - 50 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; 2,4,6-trichlorobenzoyl chloride; triethylamine; In N,N-dimethyl-formamide; toluene; benzene; 1.1: |Yamaguchi Lactonization / 2.1: |Stille Cross Coupling;
DOI:10.1021/ol302219x

Reference yield:

: 1174549-23-5
(Z)-5-((tert-butyldimethylsilyl)oxy)-3-iodopent-2-enoic acid

: 1394247-89-2
(E)-(2S,4R,6R)-2-methoxy-2-((E)-3-methyl-5-phenylpent-3-en-1-yl)-6-((E)-2-methylhexa-2,5-dien-1-yl)tetrahydro-2H-pyran-4-yl 3-(2-((tert-butyldimethylsilyl)oxy)ethyl)hexa-2,5-dienoate

Guidance literature:: Multi-step reaction with 2 steps

1.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / toluene / 2 h / 0 °C

1.2: 0 °C

2.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide; benzene / 6 h / 45 - 50 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; 2,4,6-trichlorobenzoyl chloride; triethylamine; In N,N-dimethyl-formamide; toluene; benzene; 1.1: |Yamaguchi Lactonization / 2.1: |Stille Cross Coupling;
DOI:10.1021/ol302219x