[1S,3R,S,5R,6R(1E,3S)7R]3-Hydroxy-6B-(3ALPHA-hydroxyoct-1-enyl)-7ALPHA-hydr

Base Information

• Chemical Name: [1S,3R,S,5R,6R(1E,3S)7R]3-Hydroxy-6B-(3ALPHA-hydroxyoct-1-enyl)-7ALPHA-hydr
• CAS No.: 51388-75-1
• Molecular Formula: C₁₅H₂₆O₄
• Molecular Weight: 270.369
• Mol file: 51388-75-1.mol

Synonyms:[1S,3R,S,5R,6R(1E,3S)7R]3-Hydroxy-6B-(3ALPHA-hydroxyoct-1-enyl)-7ALPHA-hydr

Chemical Property of [1S,3R,S,5R,6R(1E,3S)7R]3-Hydroxy-6B-(3ALPHA-hydroxyoct-1-enyl)-7ALPHA-hydr

Chemical Property:

• PSA: 69.92000
• LogP: 1.58810

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of [1S,3R,S,5R,6R(1E,3S)7R]3-Hydroxy-6B-(3ALPHA-hydroxyoct-1-enyl)-7ALPHA-hydr

There total 64 articles about [1S,3R,S,5R,6R(1E,3S)7R]3-Hydroxy-6B-(3ALPHA-hydroxyoct-1-enyl)-7ALPHA-hydr 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: 100.0%

7-endo-hydroxy-6-exo-(3'-hydroxyoct-1'-enyl)-3-methoxy-2-oxabicyclo<3.3.0>octane (26114-74-9,50409-26-2,54483-46-4,59829-47-9,59829-48-0,70774-01-5,70774-02-6,92077-40-2,92077-41-3,92077-42-4,92077-43-5,92077-49-1,92077-50-4,114182-97-7,114183-07-2) → (3aR,4R,5R,6aS)-4-((E)-3-Hydroxy-oct-1-enyl)-hexahydro-cyclopenta[b]furan-2,5-diol (51388-75-1,59829-49-1,59829-50-4,59829-51-5,59829-52-6,85550-76-1,85550-82-9,136235-23-9,136235-24-0)

Guidance literature:

With hydrogenchloride; In water; acetonitrile; for 3h;

Reference yield: 98.0%

(E)-(S)-1-[(3aR,4R,5R,6aS)-5-(tert-Butyl-dimethyl-silanyloxy)-2-ethoxy-hexahydro-cyclopenta[b]furan-4-yl]-oct-1-en-3-ol (104015-26-1,136235-22-8) → (3aR,4R,5R,6a5)-4-[(E,3S)-3-Hydroxy-1-octenyl]perhydrocyclopenta[b]fura n-2,5-diol (51388-75-1,59829-49-1,59829-50-4,59829-51-5,59829-52-6,85550-76-1,85550-82-9,136235-23-9,136235-24-0)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; Ambient temperature;

DOI:10.1021/ja00280a043

Reference yield:

(-)-(1S,5R)-2-oxabicyclo[3.3.0]oct-6-en-3-one (26054-46-6) → (3aR,4R,5R,6a5)-4-[(E,3S)-3-Hydroxy-1-octenyl]perhydrocyclopenta[b]fura n-2,5-diol (51388-75-1,59829-49-1,59829-50-4,59829-51-5,59829-52-6,85550-76-1,85550-82-9,136235-23-9,136235-24-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: formic acid; sulfuric acid / 24 h / 80 °C

1.2: 2 h / 0 - 20 °C

2.1: [bis(acetoxy)iodo]benzene; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / dichloromethane; N,N-dimethyl acetamide / 6 h / 20 °C

3.1: sodium hydride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

3.2: 6 h / 0 - 20 °C / Inert atmosphere

4.1: (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; dimethylsulfide borane complex / tetrahydrofuran; toluene / 1 h / -30 °C

5.1: diisobutylaluminium hydride / dichloromethane / 2 h / -78 °C

With formic acid; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; dimethylsulfide borane complex; sulfuric acid; sodium hydride; diisobutylaluminium hydride; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; dichloromethane; N,N-dimethyl acetamide; toluene; 3.1: |Horner-Wadsworth-Emmons Olefination / 3.2: |Horner-Wadsworth-Emmons Olefination / 4.1: |Corey-Bakshi-Shibata Reduction;

DOI:10.1002/anie.201902371

upstream raw materials:

Acetic acid (3aR,4R,5R,6aS)-4-((E)-(S)-3-acetoxy-oct-1-enyl)-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester

(1R,2R,3R,5S)-3-Hydroxy-2-((E)-(S)-3-hydroxy-oct-1-enyl)-bicyclo[3.2.0]heptan-6-one

(E)-(S)-1-[(3aR,4R,5R,6aS)-5-(tert-Butyl-dimethyl-silanyloxy)-2-ethoxy-hexahydro-cyclopenta[b]furan-4-yl]-oct-1-en-3-ol

(1S,4R)-4-hydroxy-2-cyclopentenyl acetate

Downstream raw materials:

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

2-[(3aR,4R,5R,6aS)-5-Hydroxy-4-((E)-(S)-3-hydroxy-oct-1-enyl)-hexahydro-cyclopenta[b]furan-(2E)-ylidene]-1-phenyl-ethanone

2-Benzenesulfinyl-2-[(3aR,4R,5R,6aS)-5-hydroxy-4-((E)-(S)-3-hydroxy-oct-1-enyl)-hexahydro-cyclopenta[b]furan-2-yl]-1-phenyl-ethanone

dinoprost

Refernces

• 1、 Zhu, Kejie,Hu, Sha,Liu, Minjie,Peng, Haihui,Chen, Fen-Er. "Access to a Key Building Block for the Prostaglandin Family via Stereocontrolled Organocatalytic Baeyer–Villiger Oxidation". . p. 9923 - 9927. Retrieved 2019/05/16.
• 2、 -. "Of the trometamol prostaglandin F2 α synthesis method (by machine translation)". . . Retrieved 2017/08/30.