(-)-ent-9(O)-methanoprostacyclin

Base Information

• Chemical Name: (-)-ent-9(O)-methanoprostacyclin
• CAS No.: 102491-28-1
• Molecular Formula: C₂₁H₃₄O₄
• Molecular Weight: 350.499
• Mol file: 102491-28-1.mol

Synonyms:

Chemical Property of (-)-ent-9(O)-methanoprostacyclin

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (-)-ent-9(O)-methanoprostacyclin

There total 50 articles about (-)-ent-9(O)-methanoprostacyclin 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:

5-[(3aS,4R,5R,6aS)-5-Acetoxy-4-((E)-(S)-3-acetoxy-oct-1-enyl)-hexahydro-pentalen-(2E)-ylidene]-pentanoic acid ethyl ester → 5-[(3aR,4S,5S,6aR)-5-Hydroxy-4-((E)-(R)-1-hydroxy-oct-2-enyl)-hexahydro-pentalen-(2E)-ylidene]-pentanoic acid + (+/-)-6,9a-methanoprostaglandin I2 (69552-46-1,69609-77-4,69609-79-6,69609-80-9,71773-66-5,71773-67-6,71773-68-7,71773-69-8,71884-21-4,71884-22-5,74035-39-5,87828-10-2,89888-72-2,89888-73-3,89888-74-4,102491-28-1,102491-29-2,123247-51-8,138381-59-6,138381-60-9)

Guidance literature:

With lithium hydroxide; In methanol; at 20 ℃; for 4h;

DOI:10.1021/ja002974x

Reference yield:

(2E,5E)-5-Allyl-deca-2,5-dienedioic acid 10-ethyl ester → (+/-)-6,9a-methanoprostaglandin I2 (69552-46-1,69609-77-4,69609-79-6,69609-80-9,71773-66-5,71773-67-6,71773-68-7,71773-69-8,71884-21-4,71884-22-5,74035-39-5,87828-10-2,89888-72-2,89888-73-3,89888-74-4,102491-28-1,102491-29-2,123247-51-8,138381-59-6,138381-60-9)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 67 percent / DMAP; DCC / CH₂Cl₂ / 2 h / 20 °C

2.1: ClTi(O-i-Pr)3; i-PrMgCl / diethyl ether; hexane / 6 h / -40 °C

2.2: diethyl ether; hexane / 0.5 h / -50 - -20 °C

3.1: 55 mg / NaBH₄ / methanol / 1 h / 0 °C

4.1: 97 percent / pyridine / 24 h / 20 °C

5.1: PdCl₂(CH₃CN)2 / tetrahydrofuran / 3 h / 20 °C

6.1: 46 mg / LiOH / methanol / 4 h / 20 °C

With pyridine; triisopropoxytitanium(IV) chloride; dmap; dichloro bis(acetonitrile) palladium(II); lithium hydroxide; sodium tetrahydroborate; isopropylmagnesium chloride; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane;

DOI:10.1021/ja002974x

Reference yield:

(E)-2-Octenal (2548-87-0) → (+/-)-6,9a-methanoprostaglandin I2 (69552-46-1,69609-77-4,69609-79-6,69609-80-9,71773-66-5,71773-67-6,71773-68-7,71773-69-8,71884-21-4,71884-22-5,74035-39-5,87828-10-2,89888-72-2,89888-73-3,89888-74-4,102491-28-1,102491-29-2,123247-51-8,138381-59-6,138381-60-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: ClTi(O-i-Pr)3; i-PrMgCl / diethyl ether; hexane / 6 h / -40 °C

1.2: diethyl ether; hexane / 0.5 h / -50 - -20 °C

2.1: 55 mg / NaBH₄ / methanol / 1 h / 0 °C

3.1: 97 percent / pyridine / 24 h / 20 °C

4.1: PdCl₂(CH₃CN)2 / tetrahydrofuran / 3 h / 20 °C

5.1: 46 mg / LiOH / methanol / 4 h / 20 °C

With pyridine; triisopropoxytitanium(IV) chloride; dichloro bis(acetonitrile) palladium(II); lithium hydroxide; sodium tetrahydroborate; isopropylmagnesium chloride; In tetrahydrofuran; methanol; diethyl ether; hexane;

DOI:10.1021/ja002974x

upstream raw materials:

(3aα,6aα)-5β-(t-butyldimethylsilyloxy)-4α-<(E)-(3S*)-3-(t-butyldimethylsilyloxy)oct-1-enyl>perhydropentalen-2-one

4-carboxybutyliden triphenylphosphorane sodium

3α-hydroxy-2β-<3α-hydroxy-1(E)-octenyl>bicyclo<3.3.0>octan-7-one

5-[(3aR,4S,5S,6aR)-5-(Tetrahydro-pyran-2-yloxy)-4-[(E)-(R)-3-(tetrahydro-pyran-2-yloxy)-oct-1-enyl]-hexahydro-pentalen-(2Z)-ylidene]-pentanoic acid methyl ester

Downstream raw materials:

(5E)-carba-PGI2

Refernces

• 1、 Okamoto,Subburaj,Sato. "Highly stereocontrolled synthesis of carbacyclin from acyclic starting materials via Ti(II)-Mediated tandem cyclization [10]". . p. 11244 - 11245. Retrieved 2007/10/03.
• 2、 Amemiya,Kojima,Sakai. "A novel synthesis of (±)-carbacyclin". . p. 1349 - 1354. Retrieved 2007/10/02.