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

Base Information

• Chemical Name: 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
• CAS No.: 107024-81-7
• Molecular Formula: C₃₁H₄₈O₅Si
• Molecular Weight: 528.805

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 4 articles about 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 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: 2.25%

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 (126327-47-7,126452-97-9) → 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) + (Z)-7-((1S,2R,3S,4R)-3-{(E)-(3R,4R)-4-[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-3-hydroxy-pent-1-enyl}-7-oxa-bicyclo[2.2.1]hept-2-yl)-hept-5-enoic acid methyl ester (107080-60-4)

Guidance literature:

With sodium tetrahydroborate; cerium(III) chloride; In tetrahydrofuran; methanol; at -50 - -30 ℃;

DOI:10.1021/jm00168a032

Reference yield:

methyl 2-<(4-tert-butyldimethylsilyloxy)phenyl>propionate (107024-79-3) → 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)

Guidance literature:

Multi-step reaction with 3 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

With 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) → 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)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With 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),4α>>-7-<3-<3-oxo-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

[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:

<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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