106402-09-9

Basic information

• Product Name: 3-oxa-9(O)-methano-delta(6,9)prostaglandin I(1)
• Synonyms: 3-oxa-9(O)-methano-delta(6,9)prostaglandin I(1)
• CAS NO: 106402-09-9
• Molecular Formula: C20H32O5
• Molecular Weight: 352.46508
• Mol File: 106402-09-9.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 525.8°Cat760mmHg
• Flash Point: 180.3°C
• Appearance: /
• Density: 1.178g/cm³
• Vapor Pressure: 2.97E-13mmHg at 25°C
• Refractive Index: 1.572
• CAS DataBase Reference: 3-oxa-9(O)-methano-delta(6,9)prostaglandin I(1)(CAS DataBase Reference)
• NIST Chemistry Reference: 3-oxa-9(O)-methano-delta(6,9)prostaglandin I(1)(106402-09-9)
• EPA Substance Registry System: 3-oxa-9(O)-methano-delta(6,9)prostaglandin I(1)(106402-09-9)

Safety Data

• Hazardous Substances Data: 106402-09-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C20H32O5/c1-2-3-4-5-16(21)6-7-17-18-11-14(8-9-25-13-20(23)24)10-15(18)12-19(17)22/h6-7,10,15-19,21-22H,2-5,8-9,11-13H2,1H3,(H,23,24)/b7-6+/t15-,16-,17+,18-,19+/m0/s1

Upstream product

• 99525-22-1 dl-3-oxa-9(O)-methano-Δ^6(9α)-prostaglandin I₁, 11,15-bis(tetrahydropyran-2-yl)ether 
• 51716-62-2 (3aR,6aS)-7,7-(ethylidene acetal)bicyclo[3.3.0]octan-3-one 
• 99524-59-1 (1S^*,5R^*)-3-(2-hydroxyethyl)-7,7-ethylenedioxybicyclo<3.3.0>oct-2-ene 
• 99524-57-9 (1S^*,5R^*)-3-methoxycarbonylmethyliden-7,7-ethylenedioxybicyclo<3.3.0>octane 
• 112329-23-4 (1R^*,5S^*)-7-(2-benzyloxyethyl)bicyclo<3.3.0.>oct-6-en-3-one 
• 99524-58-0 (1S^*,5R^*)-3-methoxycarbonylmethyl-7,7-ethylenedioxybicyclo<3.3.0>oct-2-ene 
• 112329-19-8 (1R^*,5S^*,6R^*,7R^*)-7-(2-benzyloxyethyl)-6,7-dihydroxybicyclo<3.3.0>octan-3-one 
• 112329-17-6 (1S^*,5R^*)-3-(2-benzyloxyethyl)-7,7-ethylenedioxybicyclo<3.3.0>oct-2-ene 
• 112329-25-6 ethyl (1S^*,2R^*,3R^*,5S^*)-7-(2-benzyloxyethyl)-3-hydroxybicyclo<3.3.0.>oct-6-ene-2-carboxylate 
• 112329-18-7 (1S^*,2R^*,3R^*,5R^*)-3-(2-benzyloxyethyl)-7,7-ethylenedioxybicyclo<3.3.0>octane-2,3-diol 
• 112329-24-5 ethyl (1S^*,2R^*,5S^*)-7-(2-benzyloxyethyl)-3-oxobicyclo<3.3.0.>oct-6-en-2-carboxylate 
• 112329-27-8 (1S^*,5S^*,6S^*,7R^*)-3-(2-benzyloxyethyl)-6-hydroxymethyl-7-(tetrahydropyran-2-yl)oxybicyclo<3.3.0.>oct-2-ene 
• 112329-20-1 (1R^*,5S^*,6R^*,7R^*)-7-(2-benzyloxyethyl)-7-hydroxy-5-methanesulphonylxybicyclo<3.3.0>octan-3-one 
• 112329-28-9 (1S^*,5S^*,6R^*,7R^*)-3-(2-benzyloxyethyl)-6-formyl-7-(tetrahydropyran-2-yl)oxybicyclo<3.3.0.>oct-2-ene 

Relevant articles and documents

Asymmetric Synthesis of 3-Oxacarbacyclin and 3-Oxaisocarbacyclin by a Common Enantioselective Deprotonation Based Route

Asymmetric total syntheses of 3-oxacarbacyclin (4) and 3-oxaisocarbacyclin (5) have been achieved by a new and common route. The key step of these syntheses is an enantioselective deprotonation of the prochiral ketone 25 with lithium (R,R)-bis(phenylethyl)amide (12) in the presence of LiCl. Treatment of the thus formed enolate 26 with ClSiEt3 gave the enol ether 27 of 92% ee in 94% yield. Deprotonation of the analogous prochiral ketone 9 with 12 in the presence of LiCl followed by reaction of the enolate 13 with ClSiEt3 led to isolation of the silyl enol ether 8b of 92% ee in 95% yield. A study of the deprotonation of 9 with the chiral lithium amides 14-19 showed that 12 in combination with LiCl is the optimal base in terms of enantioselectivity and accessibility. The ω-side chain in 4 and 5 was established by a Mukaiyama reaction of 27 with the unsaturatcd aldehyde 28, leading to ketone 39 of 90% de, in combination with a stereoselective Pd-catalyzed allylic rearrangement of acetate 47 to the isomeric acetate 48 and a Mitsunobu reaction of the allylic alcohol 49. The key step in the construction of the α-side chain in 4 is a Horner-Wadsworth-Emmons reaction of ketone 7c with the 8-phenylnormenthol-containing phosphonoacetate 56 which gave ester 60 of 90% de. Ester 60 was obtained diastereomerically pure by chromatography in 72% yield from 7c. Reduction of 60 furnished the allylic alcohol 62 which was converted to 4 in a standard fashion. It is at the stage of the α,ss-unsaturated ester 60 where divergence into synthesis of 5 was made. Selective isomerization of 60 to the ss,γ-unsaturated ester 66 of 97% ie in 91% yield was accomplished by deprotonation of 60 with 12 to enolate 65 and its subsequent regioselective protonation. By a similar reaction sequence the isomeric α,ss-unsaturated ester 61 was converted to the ss,γ-unsaturated ester 69 of 97% ie in 88% yield. Reduction of 66 afforded the homoallylic alcohol 71 which was converted to 5 in a standard fashion.

A stereoselective synthesis of a stable prostacyclin analogue; dl-3-oxa-9(O)-methano-Δ(6(9α))-prostaglandin I1

-