(Z)-7-[(1S,2R,3S,4R)-3-[(E,3S)-3-hydroxyoct-1-enyl]-7-oxabicyclo[2.2.1]heptan-2-yl]hept-5-enoic acid

Base Information

Chemical Name:(Z)-7-[(1S,2R,3S,4R)-3-[(E,3S)-3-hydroxyoct-1-enyl]-7-oxabicyclo[2.2.1]heptan-2-yl]hept-5-enoic acid
CAS No.:79703-24-5
Molecular Formula:C₂₁H₃₄O₄
Molecular Weight:350.499
Hs Code.:

Synonyms:8(R)9(s)11(R)12(S)-9 alpha-homo-9,11-epoxy-5(Z),13(E)-15S-hydroxyprostadienoic acid;SQ 24775;SQ 26536;SQ 26536, (1alpha,2alpha(Z),3alpha(1E,3S*),4alpha)-isomer;SQ 26536, (1S-(1alpha,2alpha(Z),3beta(1E,3R*),4alpha))-isomer;SQ 26655;SQ-24775;SQ-26,536;SQ-26536;SQ-26655

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (Z)-7-[(1S,2R,3S,4R)-3-[(E,3S)-3-hydroxyoct-1-enyl]-7-oxabicyclo[2.2.1]heptan-2-yl]hept-5-enoic acid

Chemical Property:

Vapor Pressure:5.65E-13mmHg at 25°C
Boiling Point:519.7°C at 760 mmHg
Flash Point:176.1°C
PSA：66.76000
Density:1.092g/cm³
LogP:4.47860
XLogP3:4.1
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:12
Exact Mass:350.24570956
Heavy Atom Count:25
Complexity:457

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Canonical SMILES:CCCCCC(C=CC1C2CCC(C1CC=CCCCC(=O)O)O2)O
Isomeric SMILES:CCCCC[C@@H](/C=C/[C@@H]1[C@H]2CC[C@@H]([C@@H]1C/C=C\CCCC(=O)O)O2)O

Technology Process of (Z)-7-[(1S,2R,3S,4R)-3-[(E,3S)-3-hydroxyoct-1-enyl]-7-oxabicyclo[2.2.1]heptan-2-yl]hept-5-enoic acid

There total 14 articles about (Z)-7-[(1S,2R,3S,4R)-3-[(E,3S)-3-hydroxyoct-1-enyl]-7-oxabicyclo[2.2.1]heptan-2-yl]hept-5-enoic acid 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:

: 98718-03-7
(Z)-7-[(1S,2R,3S,4R)-3-((E)-(S)-3-Hydroxy-oct-1-enyl)-7-oxa-bicyclo[2.2.1]hept-2-yl]-hept-5-enoic acid methyl ester

: 79703-24-5
<1S-(1α,2β(5Z),3β(1E,3S^*),4α)>-7-<3-(3-hydroxy-1-octenyl)-7-oxabicyclo<2.2.1>heptan-1-yl>-5-heptanoic acid

Guidance literature:: With lithium hydroxide; In tetrahydrofuran; water; at 0 - 25 ℃; for 5h;
DOI:10.1021/jm00149a007

Reference yield:

: 94903-80-7
[1S-[1α,2α(5Z)3α,4α]]-7-[3-Formyl-7-oxabicyclo[2.2.1]hept-2-yl]-5-heptenoic acid, methyl ester

: 79703-24-5
<1S-(1α,2β(5Z),3β(1E,3S^*),4α)>-7-<3-(3-hydroxy-1-octenyl)-7-oxabicyclo<2.2.1>heptan-1-yl>-5-heptanoic acid

Guidance literature:: Multi-step reaction with 3 steps

1: 1,2-dimethoxy-ethane / 3 h

2: CeCl₃*8H₂O, NaBH₄ / methanol / 0.12 h

3: LiOH / tetrahydrofuran; H₂O / 5 h / 0 - 25 °C

With lithium hydroxide; sodium tetrahydroborate; cerium(III) chloride; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; water;
DOI:10.1021/jm00149a007

Reference yield:

: 41723-91-5
4-carboxybutyliden triphenylphosphorane sodium

: 79703-24-5
<1S-(1α,2β(5Z),3β(1E,3S^*),4α)>-7-<3-(3-hydroxy-1-octenyl)-7-oxabicyclo<2.2.1>heptan-1-yl>-5-heptanoic acid

Guidance literature:: Multi-step reaction with 6 steps

1: dimsyl / dimethylsulfoxide / 2 h / 25 °C

2: diethyl ether

3: chromium oxide, pyridine / CH₂Cl₂ / 0.5 h / 25 °C

4: 1,2-dimethoxy-ethane / 3 h

5: CeCl₃*8H₂O, NaBH₄ / methanol / 0.12 h

6: LiOH / tetrahydrofuran; H₂O / 5 h / 0 - 25 °C

With pyridine; chromium(III) oxide; lithium hydroxide; sodium tetrahydroborate; cerium(III) chloride; dimethyl sulfoxide; deprotonated form; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; dichloromethane; water; dimethyl sulfoxide;
DOI:10.1021/jm00149a007