methyl <1S-<1α,2α(Z),3α(E,3S^*,4R^*),4α>>-7-<3-<4-phenyl-3-(tetrahydropyranyloxy)-1-pentenyl>-7-oxabicyclo<2.2.1>hept-2-yl>-5-heptenoate

Base Information

• Chemical Name: methyl <1S-<1α,2α(Z),3α(E,3S^*,4R^*),4α>>-7-<3-<4-phenyl-3-(tetrahydropyranyloxy)-1-pentenyl>-7-oxabicyclo<2.2.1>hept-2-yl>-5-heptenoate
• CAS No.: 101399-94-4
• Molecular Formula: C₃₀H₄₂O₅
• Molecular Weight: 482.66

Synonyms:methyl <1S-<1α,2α(Z),3α(E,3S^*,4R^*),4α>>-7-<3-<4-phenyl-3-(tetrahydropyranyloxy)-1-pentenyl>-7-oxabicyclo<2.2.1>hept-2-yl>-5-heptenoate

Chemical Property of methyl <1S-<1α,2α(Z),3α(E,3S^*,4R^*),4α>>-7-<3-<4-phenyl-3-(tetrahydropyranyloxy)-1-pentenyl>-7-oxabicyclo<2.2.1>hept-2-yl>-5-heptenoate

Chemical Property:

Purity/Quality:

99% ，98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl <1S-<1α,2α(Z),3α(E,3S^*,4R^*),4α>>-7-<3-<4-phenyl-3-(tetrahydropyranyloxy)-1-pentenyl>-7-oxabicyclo<2.2.1>hept-2-yl>-5-heptenoate

There total 4 articles about methyl <1S-<1α,2α(Z),3α(E,3S^*,4R^*),4α>>-7-<3-<4-phenyl-3-(tetrahydropyranyloxy)-1-pentenyl>-7-oxabicyclo<2.2.1>hept-2-yl>-5-heptenoate 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: 92.0%

3,4-dihydro-2H-pyran (110-87-2) + (Z)-7-[(1S,2R,3S,4R)-3-((E)-(3R,4S)-3-Hydroxy-4-phenyl-pent-1-enyl)-7-oxa-bicyclo[2.2.1]hept-2-yl]-hept-5-enoic acid methyl ester (101399-92-2) → methyl <1S-<1α,2α(Z),3α(E,3S*,4R*),4α>>-7-<3-<4-phenyl-3-(tetrahydropyranyloxy)-1-pentenyl>-7-oxabicyclo<2.2.1>hept-2-yl>-5-heptenoate (101399-94-4)

Guidance literature:

With toluene-4-sulfonic acid; In dichloromethane; at 0 - 5 ℃; for 0.666667h;

DOI:10.1021/jm00168a032

Reference yield:

(S)-(+)-dimethyl (2-oxo-3-phenylbutyl)phosphonate (62110-78-5) → methyl <1S-<1α,2α(Z),3α(E,3S*,4R*),4α>>-7-<3-<4-phenyl-3-(tetrahydropyranyloxy)-1-pentenyl>-7-oxabicyclo<2.2.1>hept-2-yl>-5-heptenoate (101399-94-4)

Guidance literature:

Multi-step reaction with 3 steps

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

2: NaBH₄, CeCl₃ / methanol / 0 °C

3: 92 percent / p-toluenesulfonic acid / CH₂Cl₂ / 0.67 h / 0 - 5 °C

With sodium tetrahydroborate; cerium(III) chloride; sodium hydride; toluene-4-sulfonic acid; In methanol; dichloromethane;

DOI:10.1021/jm00168a032

Reference yield:

[1S-[1α,2α(5Z)3α,4α]]-7-[3-Formyl-7-oxabicyclo[2.2.1]hept-2-yl]-5-heptenoic acid, methyl ester (94903-80-7) → methyl <1S-<1α,2α(Z),3α(E,3S*,4R*),4α>>-7-<3-<4-phenyl-3-(tetrahydropyranyloxy)-1-pentenyl>-7-oxabicyclo<2.2.1>hept-2-yl>-5-heptenoate (101399-94-4)

Guidance literature:

Multi-step reaction with 3 steps

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

2: NaBH₄, CeCl₃ / methanol / 0 °C

3: 92 percent / p-toluenesulfonic acid / CH₂Cl₂ / 0.67 h / 0 - 5 °C

With sodium tetrahydroborate; cerium(III) chloride; sodium hydride; toluene-4-sulfonic acid; In methanol; dichloromethane;

DOI:10.1021/jm00168a032

upstream raw materials:

3,4-dihydro-2H-pyran

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

(S)-(+)-dimethyl (2-oxo-3-phenylbutyl)phosphonate

[1S-[1α,2α(5Z)3α,4α]]-7-[3-Formyl-7-oxabicyclo[2.2.1]hept-2-yl]-5-heptenoic acid, methyl ester

Downstream raw materials:

(Z)-2-Phenylselanyl-7-{(1S,2R,3S,4R)-3-[(E)-(3R,4S)-4-phenyl-3-(tetrahydro-pyran-2-yloxy)-pent-1-enyl]-7-oxa-bicyclo[2.2.1]hept-2-yl}-hept-5-enoic acid methyl ester

methyl <1S-<1α,2α(Z),3α(E,3S^*,4R^*),4α>>-2-methyl-7-<3-<4-phenyl-3-(tetrahydropyranyloxy)-1-pentenyl>-7-oxabicyclo<2.2.1>hept-2-yl>-5-heptenoate

<1S<1α,2α(2E,5E),3α(E,3S^*,4R^*),4α>>-7-<3-(3-hydroxy-4-phenyl-1-pentenyl)-7-oxabicyclo<2.2.1>hept-2-yl>-2,5-heptadienoic acid

<1S<1α,2α(Z),3α(E,3S^*,4R^*),4α>>-7-<3-(3-hydroxy-4-phenyl-1-pentenyl)-7-oxabicyclo<2.2.1>hept-2-yl>-3-methyl-5-heptenoic acid

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