(4R,5R)-4-((E)-(S)-3-Acetoxy-oct-1-enyl)-5-((Z)-6-methoxycarbonyl-hex-2-enyl)-6-oxo-cyclohex-1-enecarboxylic acid ethyl ester

Base Information

Chemical Name:(4R,5R)-4-((E)-(S)-3-Acetoxy-oct-1-enyl)-5-((Z)-6-methoxycarbonyl-hex-2-enyl)-6-oxo-cyclohex-1-enecarboxylic acid ethyl ester
CAS No.:89560-28-1
Molecular Formula:C₂₇H₄₀O₇
Molecular Weight:476.61
Hs Code.:

Synonyms:(4R,5R)-4-((E)-(S)-3-Acetoxy-oct-1-enyl)-5-((Z)-6-methoxycarbonyl-hex-2-enyl)-6-oxo-cyclohex-1-enecarboxylic acid ethyl ester

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Chemical Property of (4R,5R)-4-((E)-(S)-3-Acetoxy-oct-1-enyl)-5-((Z)-6-methoxycarbonyl-hex-2-enyl)-6-oxo-cyclohex-1-enecarboxylic acid ethyl ester

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Technology Process of (4R,5R)-4-((E)-(S)-3-Acetoxy-oct-1-enyl)-5-((Z)-6-methoxycarbonyl-hex-2-enyl)-6-oxo-cyclohex-1-enecarboxylic acid ethyl ester

There total 11 articles about (4R,5R)-4-((E)-(S)-3-Acetoxy-oct-1-enyl)-5-((Z)-6-methoxycarbonyl-hex-2-enyl)-6-oxo-cyclohex-1-enecarboxylic acid ethyl 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: 59.0%

: 89560-27-0,89616-98-8
(3R,4R)-4-((E)-(S)-3-Acetoxy-oct-1-enyl)-3-((Z)-6-methoxycarbonyl-hex-2-enyl)-2-oxo-1-phenylselanyl-cyclohexanecarboxylic acid ethyl ester

: 89560-28-1
(4R,5R)-4-((E)-(S)-3-Acetoxy-oct-1-enyl)-5-((Z)-6-methoxycarbonyl-hex-2-enyl)-6-oxo-cyclohex-1-enecarboxylic acid ethyl ester

Guidance literature:: With dihydrogen peroxide; In dichloromethane; at 0 - 30 ℃; for 0.5h;
DOI:10.1016/S0040-4020(01)88650-6

Reference yield:

: 36323-03-2
(5Z,13E)-15-acetyl-oxy-9-oxo-prosta-5,10,13-trien-1-oic acid methyl ester

: 89560-28-1
(4R,5R)-4-((E)-(S)-3-Acetoxy-oct-1-enyl)-5-((Z)-6-methoxycarbonyl-hex-2-enyl)-6-oxo-cyclohex-1-enecarboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 5 steps

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

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

3: 70 percent / CrO₃, Celite / CH₂Cl₂; pyridine / 0.33 h / 0 °C

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

5: 59 percent / 35percent H₂O₂ / CH₂Cl₂ / 0.5 h / 0 - 30 °C

With chromium(VI) oxide; sodium tetrahydroborate; Celite; boron trifluoride diethyl etherate; dihydrogen peroxide; sodium hydride; pyridinium chlorochromate; In pyridine; dichloromethane;
DOI:10.1016/S0040-4020(01)88650-6

Reference yield:

: 31753-17-0
prostaglandin E₂

: 89560-28-1
(4R,5R)-4-((E)-(S)-3-Acetoxy-oct-1-enyl)-5-((Z)-6-methoxycarbonyl-hex-2-enyl)-6-oxo-cyclohex-1-enecarboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 6 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

With chromium(VI) oxide; sodium tetrahydroborate; Celite; boron trifluoride diethyl etherate; dihydrogen peroxide; sodium hydride; pyridinium chlorochromate; In pyridine; dichloromethane;
DOI:10.1016/S0040-4020(01)88650-6