49852-81-5

Basic information

• Product Name: prostaglandin D2 methyl ester
• Synonyms: prostaglandin D2 methyl ester;WNBMQMMGBBWUOZ-BYNKDMOPSA-N
• CAS NO: 49852-81-5
• Molecular Formula: C21H34O5
• Molecular Weight: 366.495
• Mol File: 49852-81-5.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 510°Cat760mmHg
• Flash Point: 169.4°C
• Appearance: /
• Density: 1.103g/cm³
• Vapor Pressure: 1.55E-12mmHg at 25°C
• Refractive Index: 1.539
• PKA: 13.85±0.60(Predicted)
• CAS DataBase Reference: prostaglandin D2 methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: prostaglandin D2 methyl ester(49852-81-5)
• EPA Substance Registry System: prostaglandin D2 methyl ester(49852-81-5)

Safety Data

• Hazardous Substances Data: 49852-81-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C21H34O5/c1-3-4-7-10-16(22)13-14-18-17(19(23)15-20(18)24)11-8-5-6-9-12-21(25)26-2/h5,8,13-14,16-19,22-23H,3-4,6-7,9-12,15H2,1-2H3/b8-5-,14-13+/t16-,17+,18+,19-/m0/s1

Upstream product

• 73588-55-3 methyl (5Z,13E)-9α,15-bis(dimethyl-t-butylsilyloxy)-11-oxoprosta-5,13-dienoate 
• 95233-93-5 2,3-trans-3,4-trans-2-ethoxycarbonyl-3-(prop-2-enyl)-4-hydroxy-cyclopentanone ethylene acetal 
• 95233-93-5 1,2-cis-2,3-trans-2-(2-propen-1-yl)-3-ethoxy-carbonyl-cyclopentan-1-ol-4-one ethylene acetal 
• 95233-92-4 4,5-trans-4-ethoxycarbonyl-5-(2-propen-1-yl)-cyclopentan-1,3-dione-3-ethylene acetal 
• 98582-54-8 methyl-(8,9-cis-9,12-trans)-9-t-butyldimethylsilyloxy-11,15-dioxo-prosta-5(Z),13(E)-dienoate-11-ethylene acetal 
• 98582-44-6 2,3-trans-3,4-trans-2-ethoxycarbonyl-3-(prop-2-enyl)-4-p-toluen-sulfonyloxy cyclopentanone ethylene acetal 
• 98582-53-7 2,3-trans-3,4-cis-2-formyl-3-(6-methoxycarbonyl-hex-2(Z)-enyl)-4-t-butyldimethylsilyloxy-cyclopentanone ethylene acetal 
• 98582-50-4 (Z)-7-[(6S,7R,8S)-6-Acetoxymethyl-8-(tert-butyl-dimethyl-silanyloxy)-1,4-dioxa-spiro[4.4]non-7-yl]-hept-5-enoic acid 
• 98582-52-6 2,3-trans-3,4-cis-2-(hydroxy-methyl)-3-(-methoxycarbonyl-hex-2(Z)-enyl)-4-t-butyldimethylsilyloxy-cyclopentanone ethylene acetal 
• 98582-51-5 (Z)-7-[(6S,7R,8S)-8-(tert-Butyl-dimethyl-silanyloxy)-6-hydroxymethyl-1,4-dioxa-spiro[4.4]non-7-yl]-hept-5-enoic acid 
• 98582-45-7 2,3-trans-3,4-cis-2-ethoxycarbonyl-3-(prop-2-enyl)-4-nitroxy-cyclopentanone ethylene acetal 
• 98582-49-1 2,3-trans-3,4-cis-2-(methyl-acetyloxy)-3-(methyl-formyl)-4-t-butyldimethylsilyloxy-cyclopentanone ethylene acetal 
• 98582-48-0 2,3-trans-3,4-cis-2-(methyl-acetyloxy)-3-(prop-2-enyl)-4-t-butyldimethylsilyloxy-cyclopentanone ethylene acetal 
• 98582-47-9 2,3-trans-3,4-cis-2-(hydroxy-methyl)-3-(prop-2-enyl)-4-t-butyldimethylsilyloxy cyclopentanone ethylene acetal 

Relevant articles and documents

PALLADIUM(0) CATALYZED REACTIONS OF 1,4-EPIPEROXIDES

The Pd(PPh3)4 catalyzed reaction of 2,3-saturated and 2,3-unsaturated 1,4-epiperoxides proceeds by courses markedly different from those of the previously reported transition metal catalyses.The Pd(0)-promoted reaction of 2,3-saturated epiperoxides gives the corresponding 4-hydroxy ketones and 1,4-diols as the major products.From 2,3-dedihydroepiperoxides are formed the corresponding 4-hydroxy enones, syn-1,2;3,4-diepoxides, and 1,4-diols.The results are interpreted in terms of competing Pd(0)/Pd(II) exchange mechanisms.Exposure of prostaglandin (PG) H2 methyl esterto Pd(PPh3)4 produces a mixture of methyl esters of PGD2, PGE2, PGF2α, and (5Z,8E,10E,12S)-12-hydroxy-5,8,10-heptadecatrienoic acid.

PROSTAGLANDINS: TOTAL SYNTHESIS OF PGD2 "via" 1,3 CYCLOPENTANEDIONE

A practical total synthesis of PGD2 starting from an acyclic precursor is reported.A novel efficient inversion of stereochemistry at C9 tosylate group "via" a SN2 displacement by tetrabutylammonium nitrate is described.

Palladium(0) Catalyzed Reaction of 1,4-Epiperoxides. Conversion of a Prostaglandin Endoperoxide to Primary Prostaglandins

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