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

Base Information

• Chemical Name: <1S-<1α,2α,(Z),3α(1E,3S^*,4R^*),4α>>-7-<3-<-hydroxy-4-(4-hydroxyphenyl)-1-pentenyl>-7-oxabicyclo<2.2.1>hept-2-yl>-5-heptenoic acid
• CAS No.: 107024-77-1
• Molecular Formula: C₂₄H₃₂O₅
• Molecular Weight: 400.515

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

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

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

There total 5 articles about <1S-<1α,2α,(Z),3α(1E,3S^*,4R^*),4α>>-7-<3-<-hydroxy-4-(4-hydroxyphenyl)-1-pentenyl>-7-oxabicyclo<2.2.1>hept-2-yl>-5-heptenoic 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: 74.0%

methyl <1S-<1α,2α(Z),3α(E,3S*,4R*),4α>>-7-<3-<3-hydroxy-4-<4-(tert-butyldimethylsiloxy)phenyl>-1-pentenyl>-7-oxabicyclo<2.2.1>hept-2-yl>-5-heptenoate (107024-81-7) → <1S-<1α,2α,(Z),3α(1E,3S*,4R*),4α>>-7-<3-<-hydroxy-4-(4-hydroxyphenyl)-1-pentenyl>-7-oxabicyclo<2.2.1>hept-2-yl>-5-heptenoic acid (107024-77-1)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; for 4.5h; Ambient temperature;

DOI:10.1021/jm00168a032

Reference yield:

methyl 2-<(4-tert-butyldimethylsilyloxy)phenyl>propionate (107024-79-3) → <1S-<1α,2α,(Z),3α(1E,3S*,4R*),4α>>-7-<3-<-hydroxy-4-(4-hydroxyphenyl)-1-pentenyl>-7-oxabicyclo<2.2.1>hept-2-yl>-5-heptenoic acid (107024-77-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 35 min, 2.) -78 deg C, 2 h,

2: 1.) LiBr, Et₃N / 1.) CH₂Cl₂, RT, 40 min, 2.) RT, overnight

3: CeCl₃*7H₂O, NaBH₄ / methanol; tetrahydrofuran / -50 - -30 °C

4: 74 percent / aq. LiOH / tetrahydrofuran / 4.5 h / Ambient temperature

With lithium hydroxide; sodium tetrahydroborate; n-butyllithium; cerium(III) chloride; triethylamine; lithium bromide; In tetrahydrofuran; methanol;

DOI:10.1021/jm00168a032

Reference yield:

dimethyl <3-<4-(tert-butyldimethylsiloxy)phenyl>-2-oxobutyl>phosphonate (107024-78-2) → <1S-<1α,2α,(Z),3α(1E,3S*,4R*),4α>>-7-<3-<-hydroxy-4-(4-hydroxyphenyl)-1-pentenyl>-7-oxabicyclo<2.2.1>hept-2-yl>-5-heptenoic acid (107024-77-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) LiBr, Et₃N / 1.) CH₂Cl₂, RT, 40 min, 2.) RT, overnight

2: CeCl₃*7H₂O, NaBH₄ / methanol; tetrahydrofuran / -50 - -30 °C

3: 74 percent / aq. LiOH / tetrahydrofuran / 4.5 h / Ambient temperature

With lithium hydroxide; sodium tetrahydroborate; cerium(III) chloride; triethylamine; lithium bromide; In tetrahydrofuran; methanol;

DOI:10.1021/jm00168a032

upstream raw materials:

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

methyl 2-<(4-tert-butyldimethylsilyloxy)phenyl>propionate

dimethyl <3-<4-(tert-butyldimethylsiloxy)phenyl>-2-oxobutyl>phosphonate

methyl <1S-<1α,2α(Z),3α(E),4α>>-7-<3-<3-oxo-4-<4-(tert-butyldimethylsiloxy)phenyl>-1-pentenyl>-7-oxabicyclo<2.2.1>hept-2-yl>-5-heptenoate

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