Iloprost-d4 (Major)

Base Information

• Chemical Name: Iloprost-d4 (Major)
• CAS No.: 1035094-10-0
• Molecular Formula: C₂₂H₃₂O₄
• Molecular Weight: 364.462
• Mol file: 1035094-10-0.mol

Synonyms:

Chemical Property of Iloprost-d4 (Major)

Chemical Property:

• Storage Temp.: Amber Vial, -20°C Freezer, Under inert atmosphere
• Solubility.: Benzene (Slightly)

Purity/Quality:

99% ^*data from raw suppliers

Iloprost-d4(Major) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: A labelled synthetic analogue of Prostacyclin (PGI2) used to treat pulmonary arterial hypertension (PAH), scleroderma, Raynaud''s phenomenon and ischemia. It acts through elevation of cAMP by binding to the prostacyclin receptor (IP receptor). Iloprost inhibits the ADP, thrombin, and collagen-induced aggregation of human platelets with an ED50 of about 13 nM. In whole animals, iloprost acts as a vasodilator, hypotensive, antidiuretic, and prolongs bleeding time.

Technology Process of Iloprost-d4 (Major)

There total 22 articles about Iloprost-d4 (Major) 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:

(E)-5-((3aS,4R,5R,6aS)-5-(tert-butyldimethylsilyloxy)-4-((3S,E)-3-(tert-butyldimethylsilyloxy)-4-methyloct-1-en-6-ynyl)hexahydropentalen-2(1H)-ylidene)-2,2,3,3-tetradeuteropentanoic acid (1202227-84-6) → (E)-2,2,3,3-d4-5-((3aS,4R,5R,6aS)-5-hydroxy-4-((3S,E)-3-hydroxy-4-methyloct-1-en-6-ynyl)hexahydropentalen-2(1H)-ylidene)pentanoic acid (1035094-10-0)

Guidance literature:

(E)-5-((3aS,4R,5R,6aS)-5-(tert-butyldimethylsilyloxy)-4-((3S,E)-3-(tert-butyldimethylsilyloxy)-4-methyloct-1-en-6-ynyl)hexahydropentalen-2(1H)-ylidene)-2,2,3,3-tetradeuteropentanoic acid; With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 60h;

With water-d2; hydrogen chloride; In tetrahydrofuran; ethyl acetate; pH=3;

Reference yield:

dimethyl (2-oxo-3-methylhept-5-ynyl)-phosphonate (70073-58-4) → (E)-2,2,3,3-d4-5-((3aS,4R,5R,6aS)-5-hydroxy-4-((3S,E)-3-hydroxy-4-methyloct-1-en-6-ynyl)hexahydropentalen-2(1H)-ylidene)pentanoic acid (1035094-10-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: sodium hydride / tetrahydrofuran / 0.5 h / 20 °C

1.2: 2 h

2.1: sodium tetrahydroborate; methanol; cerium(III) chloride heptahydrate / 0.75 h / -78 °C

2.2: -78 - 20 °C

3.1: water / toluene-4-sulfonic acid / acetone / 12 h / 20 °C

4.1: 1H-imidazole / N,N-dimethyl-formamide / 14 h / 20 °C

5.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / Inert atmosphere

5.2: Inert atmosphere

6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 60 h

6.2: pH 3

With 1H-imidazole; methanol; sodium tetrahydroborate; cerium(III) chloride heptahydrate; potassium tert-butylate; tetrabutyl ammonium fluoride; water; sodium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; N,N-dimethyl-formamide; acetone;

Reference yield:

(3a'S,4'R,5'R,6a'R)-5'-(tert-butyldimethylsilyloxy)-5,5-dimethylhexahydro-1'H-spiro[[1,3]dioxane-2,2'-pentalene]-4'-carbaldehyde (116855-79-9) → (E)-2,2,3,3-d4-5-((3aS,4R,5R,6aS)-5-hydroxy-4-((3S,E)-3-hydroxy-4-methyloct-1-en-6-ynyl)hexahydropentalen-2(1H)-ylidene)pentanoic acid (1035094-10-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: sodium hydride / tetrahydrofuran / 0.5 h / 20 °C

1.2: 2 h

2.1: sodium tetrahydroborate; methanol; cerium(III) chloride heptahydrate / 0.75 h / -78 °C

2.2: -78 - 20 °C

3.1: water / toluene-4-sulfonic acid / acetone / 12 h / 20 °C

4.1: 1H-imidazole / N,N-dimethyl-formamide / 14 h / 20 °C

5.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / Inert atmosphere

5.2: Inert atmosphere

6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 60 h

6.2: pH 3

With 1H-imidazole; methanol; sodium tetrahydroborate; cerium(III) chloride heptahydrate; potassium tert-butylate; tetrabutyl ammonium fluoride; water; sodium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; N,N-dimethyl-formamide; acetone;

upstream raw materials:

dimethyl (2-oxo-3-methylhept-5-ynyl)-phosphonate

(3a'S,4'R,5'R,6a'R)-5'-(tert-butyldimethylsilyloxy)-5,5-dimethylhexahydro-1'H-spiro[[1,3]dioxane-2,2'-pentalene]-4'-carbaldehyde

[(3a'S,4'S,5'R,6a'R)-5'-(tert-butyldimethylsilyloxy)-5,5-dimethylhexahydro-1'H-spiro[[1,3]dioxane-2,2'-pentalen]-4'-yl]methanol

2-methylhex-4-ynoic acid

Refernces