methyl (6S,9α,11α,13E,15S)-6,9-epoxy-11,15-dihydroxy-5-(phenylseleno)-prosta-13-en-1-oate

Base Information

• Chemical Name: methyl (6S,9α,11α,13E,15S)-6,9-epoxy-11,15-dihydroxy-5-(phenylseleno)-prosta-13-en-1-oate
• CAS No.: 78478-38-3
• Molecular Formula: C₂₇H₄₀O₅Se
• Molecular Weight: 523.572

Synonyms:methyl (6S,9α,11α,13E,15S)-6,9-epoxy-11,15-dihydroxy-5-(phenylseleno)-prosta-13-en-1-oate

Chemical Property of methyl (6S,9α,11α,13E,15S)-6,9-epoxy-11,15-dihydroxy-5-(phenylseleno)-prosta-13-en-1-oate

Chemical Property:

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Technology Process of methyl (6S,9α,11α,13E,15S)-6,9-epoxy-11,15-dihydroxy-5-(phenylseleno)-prosta-13-en-1-oate

There total 1 articles about methyl (6S,9α,11α,13E,15S)-6,9-epoxy-11,15-dihydroxy-5-(phenylseleno)-prosta-13-en-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: 28.0%

Phenylselenyl chloride (5707-04-0) + (+)-prostaglandin F2α (33854-16-9) → methyl (6S,9α,11α,13E,15S)-6,9-epoxy-11,15-dihydroxy-5-(phenylseleno)-prosta-13-en-1-oate (78478-38-3) + methyl (6R,9α,11α,13E,15S)-6,9-epoxy-11,15-dihydroxy-5-(phenylseleno)-prosta-13-en-1-oate (78478-37-2)

Guidance literature:

In dichloromethane; at -78 ℃;

DOI:10.1021/ja00402a037

Reference yield:

methyl (6S,9α,11α,13E,15S)-6,9-epoxy-11,15-dihydroxy-5-(phenylseleno)-prosta-13-en-1-oate (78478-38-3) → γ-(6R,9α,11α,13E,15S)-6,9-epoxy-4,11,15-trihydroxy-5-(phenylseleno)-prosta-13-en-1-oic acid lactone (71425-68-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / hydrogen peroxide / tetrahydrofuran / 15 h / Ambient temperature

2: 97 percent / aq. lithium hydroxide / tetrahydrofuran / 12 h / Ambient temperature

3: 68 percent / CH₂Cl₂ / -78 °C

With lithium hydroxide; dihydrogen peroxide; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja00402a037

Reference yield:

methyl (6S,9α,11α,13E,15S)-6,9-epoxy-11,15-dihydroxy-5-(phenylseleno)-prosta-13-en-1-oate (78478-38-3) → (Z)-7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-((E)-(S)-3-hydroxy-oct-1-enyl)-cyclopentyl]-hept-5-enoic acid methyl ester (13228-05-2,28977-26-6,33854-16-9,37107-45-2,37495-67-3,39645-54-0,42586-87-8,53275-50-6,53275-51-7,53275-52-8,53275-58-4,53276-25-8,57794-75-9,57794-76-0,58407-22-0,58407-23-1,62446-72-4,62446-73-5,62446-74-6,62446-75-7,63598-54-9,70773-78-3,88391-41-7,88547-65-3,96244-10-9,96244-11-0,100019-30-5)

Guidance literature:

Yield given. Multistep reaction;

DOI:10.1021/ja00402a037

upstream raw materials:

Phenylselenyl chloride

(+)-prostaglandin F_2α

Downstream raw materials:

(Z)-7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-((E)-(S)-3-hydroxy-oct-1-enyl)-cyclopentyl]-hept-5-enoic acid methyl ester

(6S)-prostaglandin I₁

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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