(Z)-7-[(1R,2R,4S,6R)-2-((E)-(S)-3-Acetoxy-oct-1-enyl)-4-acetylsulfanyl-6-methanesulfonyloxy-cyclohexyl]-hept-5-enoic acid methyl ester

Base Information

Chemical Name:(Z)-7-[(1R,2R,4S,6R)-2-((E)-(S)-3-Acetoxy-oct-1-enyl)-4-acetylsulfanyl-6-methanesulfonyloxy-cyclohexyl]-hept-5-enoic acid methyl ester
CAS No.:81755-83-1
Molecular Formula:C₂₇H₄₄O₈S₂
Molecular Weight:560.774
Hs Code.:

Synonyms:(Z)-7-[(1R,2R,4S,6R)-2-((E)-(S)-3-Acetoxy-oct-1-enyl)-4-acetylsulfanyl-6-methanesulfonyloxy-cyclohexyl]-hept-5-enoic acid methyl ester

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Chemical Property of (Z)-7-[(1R,2R,4S,6R)-2-((E)-(S)-3-Acetoxy-oct-1-enyl)-4-acetylsulfanyl-6-methanesulfonyloxy-cyclohexyl]-hept-5-enoic acid methyl ester

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Technology Process of (Z)-7-[(1R,2R,4S,6R)-2-((E)-(S)-3-Acetoxy-oct-1-enyl)-4-acetylsulfanyl-6-methanesulfonyloxy-cyclohexyl]-hept-5-enoic acid methyl ester

There total 23 articles about (Z)-7-[(1R,2R,4S,6R)-2-((E)-(S)-3-Acetoxy-oct-1-enyl)-4-acetylsulfanyl-6-methanesulfonyloxy-cyclohexyl]-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: 68.0%

: 124-63-0
methanesulfonyl chloride

: 89617-00-5
(+)-11α-acetylthio-11-deoxy-11α-homoprostaglandin F_2β 15-acetate methyl ester

: 81755-83-1
(Z)-7-[(1R,2R,4S,6R)-2-((E)-(S)-3-Acetoxy-oct-1-enyl)-4-acetylsulfanyl-6-methanesulfonyloxy-cyclohexyl]-hept-5-enoic acid methyl ester

Guidance literature:: With triethylamine; In dichloromethane; at -25 ℃; for 0.166667h;
DOI:10.1016/S0040-4020(01)88650-6

Reference yield: 68.0%

: 89560-32-7,89617-00-5
(Z)-7-[(1R,2R,4S,6R)-2-((E)-3-Acetoxy-oct-1-enyl)-4-acetylsulfanyl-6-hydroxy-cyclohexyl]-hept-5-enoic acid methyl ester

: 124-63-0
methanesulfonyl chloride

: 81755-83-1
(Z)-7-[(1R,2R,4S,6R)-2-((E)-3-Acetoxy-oct-1-enyl)-4-acetylsulfanyl-6-methanesulfonyloxy-cyclohexyl]-hept-5-enoic acid methyl ester

Guidance literature:: With triethylamine;
DOI:10.1016/S0040-4039(01)92486-4

Reference yield:

: 31753-17-0
prostaglandin E₂

: 81755-83-1
(Z)-7-[(1R,2R,4S,6R)-2-((E)-(S)-3-Acetoxy-oct-1-enyl)-4-acetylsulfanyl-6-methanesulfonyloxy-cyclohexyl]-hept-5-enoic acid methyl ester

Guidance literature:: Multi-step reaction with 11 steps

1: 87 percent / pyridine / 15 h / Ambient temperature

2: 1.) NaBH₄, 2.) PCC / 1.) EtOH, 25 deg C, 1 h, 2.) CH₂Cl₂, r.t., 4 h

3: 1.) BF₃*Et₂O, 2.) NaBH₄ / 1.) ether, 0 deg C, 2 h, 2.) MeOH, -50 deg C, 40 min

4: 70 percent / CrO₃, Celite / CH₂Cl₂; pyridine / 0.33 h / 0 °C

5: 1.) NaH / 1.) THF, -25 deg C, 30 min, 0 deg C, 15 min, 2.) THF, 0 deg C, 20 min

6: 59 percent / 35percent H₂O₂ / CH₂Cl₂ / 0.5 h / 0 - 30 °C

7: diisipropylethylamine / dimethylformamide / 3 h / Ambient temperature

8: NaCl, H₂O / dimethylsulfoxide / 2 h / 150 °C

9: 56 percent / methanol / 1.) -78 deg C, 1 h, 2.) r.t., 1 h

10: 24 percent / Zn(BH₄)2 / 1,2-dimethoxy-ethane / 2.5 h / 0 °C

11: 68 percent / Et₃N / CH₂Cl₂ / 0.17 h / -25 °C

With chromium(VI) oxide; sodium tetrahydroborate; zinc(II) tetrahydroborate; Celite; boron trifluoride diethyl etherate; water; dihydrogen peroxide; sodium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; sodium chloride; In pyridine; methanol; 1,2-dimethoxyethane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)88650-6