methyl (4E,6S,9α,11α,13E,15S)-6,9-epoxy-11,15-dihydroxyprosta-4,13-dien-1-oate

Base Information

• Chemical Name: methyl (4E,6S,9α,11α,13E,15S)-6,9-epoxy-11,15-dihydroxyprosta-4,13-dien-1-oate
• CAS No.: 67529-24-2
• Molecular Formula: C₂₁H₃₄O₅
• Molecular Weight: 366.498

Synonyms:methyl (4E,6S,9α,11α,13E,15S)-6,9-epoxy-11,15-dihydroxyprosta-4,13-dien-1-oate

Chemical Property of methyl (4E,6S,9α,11α,13E,15S)-6,9-epoxy-11,15-dihydroxyprosta-4,13-dien-1-oate

Chemical Property:

Purity/Quality:

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Technology Process of methyl (4E,6S,9α,11α,13E,15S)-6,9-epoxy-11,15-dihydroxyprosta-4,13-dien-1-oate

There total 4 articles about methyl (4E,6S,9α,11α,13E,15S)-6,9-epoxy-11,15-dihydroxyprosta-4,13-dien-1-oate 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: 56.0%

(R)-5-[(2R,3aR,4R,5R,6aS)-5-Hydroxy-4-((E)-(R)-3-hydroxy-oct-1-enyl)-hexahydro-cyclopenta[b]furan-2-yl]-5-methanesulfonyloxy-pentanoic acid methyl ester (65844-23-7,80300-73-8,80300-74-9,91840-61-8,91840-62-9,91840-63-0) → (+/-)-15-epi-prostaglandin I2 methyl ester (61799-74-4,63557-59-5,64812-61-9,70773-80-7,75419-26-0,75419-27-1,75419-28-2,75420-33-6,80300-75-0,80300-76-1) + (E)-5-[(2S,3aS,4S,5S,6aR)-5-Hydroxy-4-((E)-(S)-3-hydroxy-oct-1-enyl)-hexahydro-cyclopenta[b]furan-2-yl]-pent-4-enoic acid methyl ester (64861-48-9,67529-24-2,67529-25-3,91840-64-1,91840-65-2,91840-66-3,91840-67-4)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; at 60 ℃; for 20h;

DOI:10.1039/P19840000675

Reference yield: 12.0%

(S)-5-[(2S,3aR,4R,5R,6aS)-5-Hydroxy-4-((E)-(R)-3-hydroxy-oct-1-enyl)-hexahydro-cyclopenta[b]furan-2-yl]-5-methanesulfonyloxy-pentanoic acid methyl ester (65844-23-7,80300-73-8,80300-74-9,91840-61-8,91840-62-9,91840-63-0) → (+/-)-15-epi-prostaglandin I2 methyl ester (61799-74-4,63557-59-5,64812-61-9,70773-80-7,75419-26-0,75419-27-1,75419-28-2,75420-33-6,80300-75-0,80300-76-1) + (E)-5-[(2R,3aS,4S,5S,6aR)-5-Hydroxy-4-((E)-(S)-3-hydroxy-oct-1-enyl)-hexahydro-cyclopenta[b]furan-2-yl]-pent-4-enoic acid methyl ester (64861-48-9,67529-24-2,67529-25-3,91840-64-1,91840-65-2,91840-66-3,91840-67-4)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; at 60 ℃; for 20h;

DOI:10.1039/P19840000675

Reference yield: 10.0%

(+/-)-(5S)-mesyloxy-(6R)-prostaglandin I1 methyl ester (65844-23-7,80300-73-8,80300-74-9,91840-61-8,91840-62-9,91840-63-0) → (+/-)-prostaglandin I2 methyl ester (61799-74-4,63557-59-5,64812-61-9,70773-80-7,75419-26-0,75419-27-1,75419-28-2,75420-33-6,80300-75-0,80300-76-1) + (E)-5-[(2R,3aS,4S,5S,6aR)-5-Hydroxy-4-((E)-(R)-3-hydroxy-oct-1-enyl)-hexahydro-cyclopenta[b]furan-2-yl]-pent-4-enoic acid methyl ester (64861-48-9,67529-24-2,67529-25-3,91840-64-1,91840-65-2,91840-66-3,91840-67-4)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; at 65 ℃; for 20h;

DOI:10.1039/P19840000675

upstream raw materials:

(+/-)-(5S)-mesyloxy-(6R)-prostaglandin I₁ methyl ester

(S)-5-[(2S,3aR,4R,5R,6aS)-5-Hydroxy-4-((E)-(R)-3-hydroxy-oct-1-enyl)-hexahydro-cyclopenta[b]furan-2-yl]-5-methanesulfonyloxy-pentanoic acid methyl ester

(+/-)-(5R)-mesyloxy-(6S)-prostaglandin I₁ methyl ester

(R)-5-[(2R,3aR,4R,5R,6aS)-5-Hydroxy-4-((E)-(R)-3-hydroxy-oct-1-enyl)-hexahydro-cyclopenta[b]furan-2-yl]-5-methanesulfonyloxy-pentanoic acid methyl ester

Downstream raw materials:

γ-(6R,9α,11α,13E,15S)-6,9-epoxy-4,11,15-trihydroxy-5-(phenylseleno)-prosta-13-en-1-oic acid lactone

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