(Z)-7-{(3R,3aR,4R,5S,6aR)-3-[3-(3-Chloro-phenoxy)-2-hydroxy-propylsulfanyl]-5-hydroxy-hexahydro-cyclopenta[c]furan-4-yl}-hept-5-enoic acid methyl ester

Base Information

Chemical Name:(Z)-7-{(3R,3aR,4R,5S,6aR)-3-[3-(3-Chloro-phenoxy)-2-hydroxy-propylsulfanyl]-5-hydroxy-hexahydro-cyclopenta[c]furan-4-yl}-hept-5-enoic acid methyl ester
CAS No.:74166-54-4
Molecular Formula:C₂₄H₃₃ClO₆S
Molecular Weight:485.041
Hs Code.:

(Z)-7-{(3R,3aR,4R,5S,6aR)-3-[3-(3-Chloro-phenoxy)-2-hydroxy-propylsulfanyl]-5-hydroxy-hexahydro-cyclopenta[c]furan-4-yl}-hept-5-enoic acid methyl ester

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Chemical Property of (Z)-7-{(3R,3aR,4R,5S,6aR)-3-[3-(3-Chloro-phenoxy)-2-hydroxy-propylsulfanyl]-5-hydroxy-hexahydro-cyclopenta[c]furan-4-yl}-hept-5-enoic acid methyl ester

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Technology Process of (Z)-7-{(3R,3aR,4R,5S,6aR)-3-[3-(3-Chloro-phenoxy)-2-hydroxy-propylsulfanyl]-5-hydroxy-hexahydro-cyclopenta[c]furan-4-yl}-hept-5-enoic acid methyl ester

There total 7 articles about (Z)-7-{(3R,3aR,4R,5S,6aR)-3-[3-(3-Chloro-phenoxy)-2-hydroxy-propylsulfanyl]-5-hydroxy-hexahydro-cyclopenta[c]furan-4-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: 85.0%

: 67741-93-9
3-(3-chlorophenoxy)-2-hydroxypropane-1-thiol

: 74166-53-3,74184-61-5
(Z)-7-((3aR,4R,5S,6aR)-3,5-Dihydroxy-hexahydro-cyclopenta[c]furan-4-yl)-hept-5-enoic acid methyl ester

: 74166-54-4,74184-62-6
(Z)-7-{(3R,3aR,4R,5S,6aR)-3-[3-(3-Chloro-phenoxy)-2-hydroxy-propylsulfanyl]-5-hydroxy-hexahydro-cyclopenta[c]furan-4-yl}-hept-5-enoic acid methyl ester

Guidance literature:: With 4 A molecular sieve; boron trifluoride diethyl etherate; In 1,2-dimethoxyethane; at 20 ℃; for 17h;
DOI:10.1246/cl.1980.175

Reference yield:

: 64782-11-2,65700-30-3,74807-10-6
tetrahydroanhydroaucubigenin-epimer benzoate

: 74166-54-4,74184-62-6
(Z)-7-{(3R,3aR,4R,5S,6aR)-3-[3-(3-Chloro-phenoxy)-2-hydroxy-propylsulfanyl]-5-hydroxy-hexahydro-cyclopenta[c]furan-4-yl}-hept-5-enoic acid methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: boron trifluoride etherate / 1,2-dimethoxy-ethane / 20 h / 20 °C

2: 1.) CrO₃*2Py; 2.) 0.33 M KOH / 1.) dichloromethane, 0 deg C, 30 min; 2.) MeOH-H₂O 2:1, 20 deg C, 17 h

3: sodium methylsulfinylmethide / dimethylsulfoxide / 5 h / 20 °C

5: CuCl₂ (1 eq) - CuO (2 eq) / acetone; H₂O / 2 h / 20 °C

6: 85 percent / boron trifluoride etherate, molecular sieves 4A / 1,2-dimethoxy-ethane / 17 h / 20 °C

With potassium hydroxide; 4 A molecular sieve; boron trifluoride diethyl etherate; dimsylsodium; dipyridine chromium trioxide; In 1,2-dimethoxyethane; water; dimethyl sulfoxide; acetone;
DOI:10.1246/cl.1980.175

Reference yield:

: 17814-85-6
(4-carboxybutyl)triphenylphosphonium bromide

: 74166-54-4,74184-62-6
(Z)-7-{(3R,3aR,4R,5S,6aR)-3-[3-(3-Chloro-phenoxy)-2-hydroxy-propylsulfanyl]-5-hydroxy-hexahydro-cyclopenta[c]furan-4-yl}-hept-5-enoic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: sodium methylsulfinylmethide / dimethylsulfoxide / 5 h / 20 °C

3: CuCl₂ (1 eq) - CuO (2 eq) / acetone; H₂O / 2 h / 20 °C

4: 85 percent / boron trifluoride etherate, molecular sieves 4A / 1,2-dimethoxy-ethane / 17 h / 20 °C

With 4 A molecular sieve; boron trifluoride diethyl etherate; dimsylsodium; In 1,2-dimethoxyethane; water; dimethyl sulfoxide; acetone;
DOI:10.1246/cl.1980.175