(Z)-7-[(1S,2R,3S,4R)-3-((E)-3-Oxo-4-phenoxy-but-1-enyl)-7-oxa-bicyclo[2.2.1]hept-2-yl]-hept-5-enoic acid methyl ester

Base Information

• Chemical Name: (Z)-7-[(1S,2R,3S,4R)-3-((E)-3-Oxo-4-phenoxy-but-1-enyl)-7-oxa-bicyclo[2.2.1]hept-2-yl]-hept-5-enoic acid methyl ester
• CAS No.: 87929-54-2
• Molecular Formula: C₂₄H₃₀O₅
• Molecular Weight: 398.499

Synonyms:(Z)-7-[(1S,2R,3S,4R)-3-((E)-3-Oxo-4-phenoxy-but-1-enyl)-7-oxa-bicyclo[2.2.1]hept-2-yl]-hept-5-enoic acid methyl ester

Chemical Property of (Z)-7-[(1S,2R,3S,4R)-3-((E)-3-Oxo-4-phenoxy-but-1-enyl)-7-oxa-bicyclo[2.2.1]hept-2-yl]-hept-5-enoic acid methyl ester

Chemical Property:

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Technology Process of (Z)-7-[(1S,2R,3S,4R)-3-((E)-3-Oxo-4-phenoxy-but-1-enyl)-7-oxa-bicyclo[2.2.1]hept-2-yl]-hept-5-enoic acid methyl ester

There total 2 articles about (Z)-7-[(1S,2R,3S,4R)-3-((E)-3-Oxo-4-phenoxy-but-1-enyl)-7-oxa-bicyclo[2.2.1]hept-2-yl]-hept-5-enoic acid methyl ester 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:

methyl (5Z)-7-(3-exo-(hydroxymethyl)-7-oxabicyclo<2.2.1>heptan-2-exo-yl)hept-5-enoate (104596-10-3) → (Z)-7-[(1S,2R,3S,4R)-3-((E)-3-Oxo-4-phenoxy-but-1-enyl)-7-oxa-bicyclo[2.2.1]hept-2-yl]-hept-5-enoic acid methyl ester (87929-54-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 0.52 g / pyridinium chlorochromate, Celite, NaOAc / CH₂Cl₂ / 1.75 h / 23 °C

2: 1.) NaH / 1.) DME, 2.) 23 deg C

With Celite; sodium acetate; sodium hydride; pyridinium chlorochromate; In dichloromethane;

DOI:10.1021/jm00168a032

Reference yield:

dimethyl (3-phenoxy-2-oxopropyl)phosphonate (40665-68-7) + methyl <1α,2α(Z),3α,4α>-7-<3-formyl-7-oxabicyclo<2.2.1>hept-2-yl>-5-heptenoate (104596-33-0) → (Z)-7-[(1S,2R,3S,4R)-3-((E)-3-Oxo-4-phenoxy-but-1-enyl)-7-oxa-bicyclo[2.2.1]hept-2-yl]-hept-5-enoic acid methyl ester (87929-54-2)

Guidance literature:

With sodium hydride; Multistep reaction; 1.) DME, 2.) 23 deg C;

DOI:10.1021/jm00168a032

Reference yield:

(Z)-7-[(1S,2R,3S,4R)-3-((E)-3-Oxo-4-phenoxy-but-1-enyl)-7-oxa-bicyclo[2.2.1]hept-2-yl]-hept-5-enoic acid methyl ester (87929-54-2) → (Z)-7-[(1S,2R,3S,4R)-3-((E)-(R)-3-Hydroxy-4-phenoxy-but-1-enyl)-7-oxa-bicyclo[2.2.1]hept-2-yl]-hept-5-enoic acid methyl ester (87929-80-4,87983-21-9)

Guidance literature:

With sodium tetrahydroborate; cerium(III) chloride; In methanol; at 0 ℃;

DOI:10.1021/jm00168a032

upstream raw materials:

dimethyl (3-phenoxy-2-oxopropyl)phosphonate

methyl <1α,2α(Z),3α,4α>-7-<3-formyl-7-oxabicyclo<2.2.1>hept-2-yl>-5-heptenoate

methyl (5Z)-7-(3-exo-(hydroxymethyl)-7-oxabicyclo<2.2.1>heptan-2-exo-yl)hept-5-enoate

Downstream raw materials:

(Z)-7-[(1S,2R,3S,4R)-3-((E)-(R)-3-Hydroxy-4-phenoxy-but-1-enyl)-7-oxa-bicyclo[2.2.1]hept-2-yl]-hept-5-enoic acid methyl ester

<1α,2α(Z),3α(E),4α>-7-<3-(3-hydroxy-4-phenoxy-1-butenyl)-7-oxabicyclo<2.2.1>hept-2-yl>-5-heptenoic acid

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