Home > Carbonyl Compounds> methyl 7-[(1R,2R,3R)-3-hydroxy-2-[(E,3R)-3-hydroxy-4-phenoxybut-1-enyl]-5-oxocyclopentyl]hepta-4,5-dienoate

methyl 7-[(1R,2R,3R)-3-hydroxy-2-[(E,3R)-3-hydroxy-4-phenoxybut-1-enyl]-5-oxocyclopentyl]hepta-4,5-dienoate

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Origin: China

Cas No: 73121-56-9

Specification: 99%min

Min order Quantity: 1 /kg

Supply Ability: 50 mt/month

Lead time: 7 days for OEM, 3 days for ready goods

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CAS No.: 73121-56-9 Formula: C23H28O6 Molecular Weight: 400.46500

Description

Enprostil is a synthetic analogue of prostaglandin E2 and was found to be effective in the treatment of patients with duodenal or gastric ulcers.

Basic Info

Chemical Name	methyl 7-[(1R,2R,3R)-3-hydroxy-2-[(E,3R)-3-hydroxy-4-phenoxybut-1-enyl]-5-oxocyclopentyl]hepta-4,5-dienoate
Synonyms	Enprostil (JAN/USAN/INN); Camleed (TN); methyl (4,5,6S)-7-<(1R,2R,3R)-3-hydroxy-2-<(E)-(3R)-3-hydroxy-4-phenoxy-1-butenyl>-5-oxocyclopentyl>-4,5-heptadienoate; Gardrine; Syngard; methyl (4,5,6R)-7-<(1R,2R,3R)-3-hydroxy-2-<(E)-(3R)-3-hydroxy-4-phenoxy-1-butenyl>-5-oxocyclopentyl>-4,5-heptadienoate; Camleed; enprostil;
CAS No.	73121-56-9
Molecular Formula	C23H28O6
Molecular Weight	400.46500
PSA	93.06000
LogP	2.60320

Properties

Density	1.201g/cm3
Boiling Point	552.9ºC at 760 mmHg
Flash Point	185.7ºC
Refractive Index	1.586

Synthesis Route

(-)-11α,15α-bis((tert-butyldimethylsilyl)oxy)-9-oxo-16-phenoxy-17,18,19,20-tetranorprosta-4,15,13(t)-trienoic acid methyl ester→methyl 7-[(1R,2R,3R)-3-hydroxy-2-[(E,3R)-3-hydroxy-4-phenoxybut-1-enyl]-5-oxocyclopentyl]hepta-4,5-dienoate
(3aR,4R,5R,6aS)-4-((3R,E)-4-phenoxy-3-((tetrahydro-2H-pyran-2-yl)oxy)but-1-en-1-yl)-5-((tetrahydro-2H-pyran-2-yl)oxy)hexahydro-2H-cyclopenta[b]furan-2-ol→methyl 7-[(1R,2R,3R)-3-hydroxy-2-[(E,3R)-3-hydroxy-4-phenoxybut-1-enyl]-5-oxocyclopentyl]hepta-4,5-dienoate
(3aR,4R,5R,6aS)-Hexahydro-4-[(E)-(3R)-4-phenoxy-3-[(tetrahydro-2H-pyran-2-yl)oxy]-1-butenyl]-5-[(tetrahydro-2H-pyran-2-yl)oxy]-2H-cyclopenta[b]furan-2-one→methyl 7-[(1R,2R,3R)-3-hydroxy-2-[(E,3R)-3-hydroxy-4-phenoxybut-1-enyl]-5-oxocyclopentyl]hepta-4,5-dienoate

Toxicity

Exposure Route	Type of Test	Species Observed	Dose/Duration	Toxic Effects
Oral	LD50 - Lethal dose, 50 percent kill	Rodent - rat	>1600 ug/kg	1.Lungs, Thorax, or Respiration-cyanosis 2.Musculoskeletal-other changes 3.Nutritional and Gross Metabolic-body temperature decrease
Intraperitoneal	LD50 - Lethal dose, 50 percent kill	Rodent - rat	>160 ug/kg	1.Details of toxic effects not reported other than lethal dose value
Oral	LD50 - Lethal dose, 50 percent kill	Rodent - mouse	1600 ug/kg	1.Sense Organs and Special Senses (Eye)-ptosis 2.Behavioral-somnolence (general depressed activity) 3.Gastrointestinal-changes in structure or function of salivary glands

Precursor

(3S,4R)-3-(Methoxymethyloxy)-2-methylidene-4-(tert-butyldimethylsiloxy)cyclopentanone
(3aR,4R,5R,6aS)-4-((3R,E)-4-phenoxy-3-((tetrahydro-2H-pyran-2-yl)oxy)but-1-en-1-yl)-5-((tetrahydro-2H-pyran-2-yl)oxy)hexahydro-2H-cyclopenta[b]furan-2-ol
(-)-11α,15α-bis((tert-butyldimethylsilyl)oxy)-9-oxo-16-phenoxy-17,18,19,20-tetranorprosta-4,15,13(t)-trienoic acid methyl ester
1-[5α-hydroxy-2β-[(E)-4-phenoxy-3α-tetrahydropyran-2-yloxy-1-butenyl]-3α-tetrahydropyran-2-yloxycyclopent-1α-yl]but-3-yn-2-ol

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