31752-99-5|(3aR,4S,5R,6aS)-4-(Hydroxymethyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl Biphenyl-4-carboxylate| Ambeed

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Quality Control of [ 31752-99-5 ] Purity: 98% SDS Specification

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Product Details of [ 31752-99-5 ]

CAS No. :	31752-99-5
Formula :	C₂₁H₂₀O₅
M.W :	352.38
SMILES Code :	O=C(C1=CC=C(C2=CC=CC=C2)C=C1)O[C@H](C3)[C@H](CO)[C@](C4)([H])[C@@]3([H])OC4=O
MDL No. :	MFCD00078077
InChI Key :	SZJVIFMPKWMGSX-AKHDSKFASA-N
Pubchem ID :	2724295

Safety of [ 31752-99-5 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 31752-99-5 ] Show Less

Physicochemical Properties

Num. heavy atoms	26
Num. arom. heavy atoms	12
Fraction Csp3	0.33
Num. rotatable bonds	5
Num. H-bond acceptors	5.0
Num. H-bond donors	1.0
Molar Refractivity	95.03
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	72.83 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.78
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	3.09
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.82
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	2.86
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	3.21
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.95

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.98
Solubility	0.0366 mg/ml ; 0.000104 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-4.29
Solubility	0.0182 mg/ml ; 0.0000516 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-5.04
Solubility	0.00323 mg/ml ; 0.00000916 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	Yes
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	Yes
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	Yes
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.26 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	0.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	1.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	3.96

Application In Synthesis of [ 31752-99-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 31752-99-5 ]

[ 31752-99-5 ] Synthesis Path-Downstream 1~35

1
[ 31752-99-5 ]
[ 124583-86-4 ]
[ 137514-76-2 ]

References: [1]Tetrahedron Asymmetry,1991,vol. 2,p. 763 - 766.

2
[ 31752-99-5 ]
[ 38754-71-1 ]

Yield	Reaction Conditions	Operation in experiment
87.3%	With 4-hydroxy-2,2,6,6-tetramethylpiperidine-N-oxyl; trichloroisocyanuric acid; In dichloromethane; at 0℃; for 1h;	(3aR,4S,5R,6aS)-(-)-hexahydro-4-(hydroxymethyl)-2-oxo-2H-cyclopenta[b]furan-5-1,1'-biphenyl-4-formate (35.5 g, 0.1 mol), TEMPO-OH (0.81 g, 0.005 mol) was dissolved in 200 mL of dichloromethane,TCCA (25.6g, 0.11mol) was added in batches at 0 C. After the addition,Reaction at 0 C for 1 hour, monitored by TLC. After the reaction, 200 mL of water was added and mixed.The organic phase was then separated, and the aqueous phase was extracted twice with dichloromethane (200 mL * 2).Combine the organic phase separated after the reaction and the organic phase obtained after extraction with the aqueous phase,The combined organic phases were dried over anhydrous sodium sulfate, filtered,The solvent was spin-dried under reduced pressure to give the target product (3aR,4R,5R,6aS)-4-aldehyde hexahydro-2-oxo-2H-cyclopenta[b]furan-5-yl [1,1'-biphenyl]-4-formate 29.1g, The yield was 87.3% and the purity was 98.3%.
	With phosphoric acid; dimethyl sulfoxide; dicyclohexyl-carbodiimide; In 1,2-dimethoxyethane;	Compound 1 was synthesized from Corey's lactone 4. The primary alcohol of lactone 4 was oxidized to aldehyde 5 with DCC, DMSO and H3PO4 in DME. The crude aldehyde 5 was reacted with dimethyl (2-oxo-4-phenylbutyl) phosphonate in the presence of lithium chloride and diisopropyl ethyl amine to give 6 in 70% yield. Stereoselective reduction of the enone 6 with S-Alphine hydride in THF at -78 C. provided 70-75% of the (15S)-7 isomer over the (15R)-7 isomer. Alternatively, the reduction could be performed with NaBH4.CeCl4(H2O)7 in MeOH/CH2Cl2 with lower selectivity. The epimers were readily separated by column chromatography on silica gel using tolene:ethyl acetate 2:1 as eluent to give pure (15-S)-7. Removal of the p-phenylbenzoyl (PPB) protective group with K2CO3 in MeOH afforded an 80% yield of the diol 8. The product 8 was purified by column chromatography on silica gel using ethyl acetate as eluent. The free hydroxyl groups of 8 were protected with tetrahydropyranyl (THP) groups to give 9 in quantitative yield. Compound 9 was treated with diisobutylaluminium hydride (DIBAL-H) in dry THF to give the lactol 10. Product 10 underwent Wittig reaction with 4-carboxybutyl-triphenylphosphonium bromide, t-BuOK in dry THF affording the acid 11. This was further reacted without isolation with isopropyl iodide in the presence of DBU in acetone to give the corresponding ester 12, which was isolated by column chromatography on silica gel using ethyl acetate:hexane 1:1. Compound 12 was oxidized with pyridinium chlorchromate treated with aluminium oxide (PCC/Al2O3) in dichloromethane to give the compound 13. The protecting groups 11, 15-bistetrahydro-pyranyloxy groups were removed by addition of 1N HCl in acetonitrile. The reaction mixture was stirred at room temperature for about 3 hrs to give 14. This was further reacted without isolation with addition of excess 1N HCl. The mixture was stirred for additional 40 hrs to accomplish quantitative conversion to the corresponding PGA2 ester analogue (1).
	With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate; sodium bromide; In dichloromethane; water; isopropyl alcohol; at -5 - 0℃; for 0.5h;	Example 1 (3aR,4R,5R,6aS)-4-(3-Oxo-5-phenyl-1E-pentenyl)-5-(4-phenylbenzoyloxy)-hexahydro-2H-cyclopenta[b]furan-2-one A solution of <strong>[31752-99-5](-)-Corey lactone 5-(4-phenylbenzoate)</strong> 9 (17.6 g, 50.0 mmol) and TEMPO (0.16 g, 1.0 mmol) in CH2Cl2 (100 mL) was added to a solution of NaBr (0.5 g, 5.0 mmol), NaHCO3 (12.6 g, 150.0 mmol) and IPA (6.0 g, 100.0 mmol) in water (100 mL). 5% aq. NaOCl (about 150 mL) was added dropwise to the stirred mixture at -5 to 0 C. until disappearance of Corey lactone (TLC monitoring). The obtained mixture was stirred for 0.5 h at the same temperature. The aqueous layer was separated and extracted with CH2Cl2 (50 mL). The combined organic layers was added dropwise over 1 h to a stirred mixture of a solution of BnCH2COCH2PO(OMe)2 (15.4 g, 60.0 mmol) in CH2Cl2 (20 mL) and 30% NaOH (8.0 g, 60.0 mmol) at 0-5 C. The mixture was stirred 0.5 h at the same temperature and treated with 10% aq. citric acid (100 mL). The aqueous layer was separated and extracted with CH2Cl2 (50 mL). The combined organic layers were dried over Na2SO4, filtered through short silica gel column and concentrated in vacuo. The oily residue (24.2 g) was dissolved in refluxed EtOH (150 mL) and cooled in ice bath. The precipitate was filtered off, washed with cold EtOH and dried in vacuo to give 20.1 g (84%) of ketone 7 with 99.4% purity by HPLC: mp 129-130 C., [alpha]20D-142 (c 1.0, CHCl3); 1H NMR (CDCl3) 2.32-2.63 (m, 3H); 2.84-2.97 (m, 7H); 5.00-5.10 (m, 1H); 5.20-5.35 (m, 1H); 6.20 (d, J=16 Hz, 1H); 6.65 (dd, J=16 and 8 Hz, 1H); 7.15-7.67 (m, 12H); 8.03 (d, J=8 Hz, 2H).

		Part-B): Preparation of Corey aldehyde from Corey lactone.Dimethoxy ethane (60ml) was charged into Corey lactone (10 g) at 25 to 30c in a 250 ml four neck round bottom flask equipped with mechanical stirrer and dropping funnel. The suspension was stirred for 10 minutes, charged dicyclohexyl carbodiimide (23.3) and dimethyl sulfoxide (DMSO) (17.75 g) at 25 to 300C. The reaction mass was cooled to 20 to 220C and phosphoric acid was added (1.65g). The reaction mixture was maintained at 20 to 22 C for about 20 to 30 minutes. The temperature was raised to 25 to 300C. After completion of reaction, the unwanted dicyclohexyl urea was filtered and washed with dimethoxy ethane (20 ml). The filtrate contains Corey aldehyde.
	With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; trichloroisocyanuric acid; potassium acetate; In dichloromethane; at -5 - 17℃; for 1.09167h;	Step C: Preparation of (3af?,4f?,5f?,6aS)-4-formyl-2-oxohexahvdro-2/-/- cvclopenta[fc>1furan-5-yl biphenyl-4-carboxylate ((-)-Corev aldehyde, PPB-protected) from (3af?,4S,5/:?,6aS)-4-(hvdroxymethyl)-2-oxohexahvdro-2/-/-cvclopenta[irj1furan-5-yl biphenyl-4-carboxylate ((-)-Corev alcohol, PPB-protected). g 4 parts ry ngTo a 20-L jacketed reactor fitted with a mechanical stirrer and a thermocouple was charged the (-)-Corey alcohol, PPB-protected (250 g, 0.71 mol, 1 molar equivalent), trichloroisocyanuric acid (66 g, 0.29 mol, 0.4 molar equivalent), potassium acetate (166.9 g, 1 .74 mol, 2.4 molar equivalents), and dichloromethane (8000 mL). The mixture was stirred and cooled to -5 C with a circulator. Once the mixture was at the desired temperature, a solution consisting of 2,2,6,6-tetramethyl- piperidin-1 -oxyl (TEMPO, 1 .13 g, 7 mmol, 0.01 molar equivalent) dissolved in dichloromethane (3 mL) was added in one portion via pipet. The mixture changed from white to a light orange within 30 seconds. The internal temperature rose to 17 C within 5 minutes. The circulator was adjusted to 3 C and the mixture was stirred for one hour. After about 15 minutes of stirring, the light orange color turned to white and the internal temperature started to gradually cool to 3 C. The resulting white slurry was treated (strongly effervesces.) with aqueous 5% w/w potassium bicarbonate (5000 mL). The resulting white reaction mixture was filtered through a coarse porosity (40-60 muiotaeta) glass fritted funnel. The filtration could be quite slow. The reactor was rinsed with dichloromethane (1000 mL). The rinse was passed through the filter. The layers of the resulting biphasic filtrate were separated and the lower dichloromethane layer was washed with 10% w/w aqueous potassium iodide (2500 mL), 10% w/w aqueous sodium thiosulfate (2500 mL), and 10% w/w potassium dihydrogenphosphate (2500 mL). The lower dichloromethane layer was dried over magnesium sulfate (500 g). The solids were filtered and the title intermediate was carried onto the next step as the filtrate solution.
	With phosphoric acid; dimethyl sulfoxide; diisopropyl-carbodiimide; In toluene; at 50℃;Inert atmosphere; Large scale;	1. Construction of the lower chain (Oxidation and HWE reaction) Preparation of the [l,l'-Biphenyl]-4-carboxylic acid, (3aR,4R,5R,6aS)-hexahydro-2- [( 1 E)-3 -oxo-4-[3 -(trifluoromethyl)phenoxy] - 1 -buten- 1 -yl] -2H-cyclopenta[b] furan-5 -yl /compound of formula (II)/ C2iH2o05 C3iH25F306 Mr: 352.39 Mr: 550.54 1069 g of PPB-Corey-lactone is suspended in an inert atmosphere in 1 1.1 L of water- free toluene. To this suspension are added 1.4 L of diisopropylcarbodiimide and then 0.855 L of dimethyl sulfoxide in phosphoric acid. The reaction mixture is heated to 50C and a further 0.34 L of dimethyl sulfoxide in phosphoric acid is added in portions. After the accomplishment of the oxidation reaction, the mixture is cooled to-10C and while that temperature is maintained, 316 g of potassium hydroxide followed by 1.45 kg of Travoprost phosphonate in toluene solution are added. When the HWE reaction has completed, the reaction mixture is poured onto 1 M hydrochloric acid solution and the mixture is stirred. The precipitated crystals are filtered off and washed. The phases of the filtrate are separated, the organic phase is washed with 1M sodium hydrogen carbonate solution and then with diluted hydrochloric acid solution. The organic phase is evaporated and purified by chromatography on a silica gel column (eluent: toluene - ethyl acetate mixture). The main fraction is evaporated and crystallized from ethyl acetate - hexane mixture. Yield: 915 g, 55 %. Melting point: 112.5-1 14.5C IR spectrum of Travoprost 1. intermediate is shown on Figure 2. Travo rost 1. intermediate , l3C and 19F NMR data: Travoprost 1. intermediate (enone - Formula (II)): 2 118.75 7.20** 1 m (dd) 3 123.95 (q) - - - 'JC-23,F _ 272.5 -61.10 3-F - - - (s, 3) 4 164.94 - - - 5 128.16 - - - 6, 26' 129.95 8.015 2 m J26,27=8.5; 7, 27' 126.87 7.81 2 m 8 144.93 - - -9 138.77 - - -0, 30' 127.01 7.74 2 m (dd) 1, 31 ' 129.10 7 5 1 * * * 2 m (t) 2 128.46 7.43 1 m (tt) ,32~1·6 , , **: Overlapping H NMR signals
	With Dess-Martin periodane; In dichloromethane; at 5 - 20℃;	a) Dess martin (132.36 g, 1.1 eq) was added to a solution of Corey's lactone (100 g, 1 eq) in DCM (1500 ml) at 5-10C. The mixture was stirred for 1-2 hrs at 15-20C. The solution was filtered and washed with DCM. DCM layer was washed with solution of sodium thiosulfate and sodium bicarbonate in DM water followed by washing with 10% NaCl solution.
	With Dess-Martin periodane; In dichloromethane; at 22℃; for 0.12h;	Dess-Martin reagent (86.66 g, 1.2 eq) was added in one portion to a 2L three-necked flask containing DCM (480 mL), mechanical stirring was started, and stirring was performed for 10 minutes to give a white cloudy solution.The ice water bath was allowed to cool for 30 min, and a solution of the compound of formula 1 (60.00 g) in DCM (240 mL) was added dropwise to the three-necked vial in about 30 min at 22C. After the medium-term addition, it is partially dissolved.Late turbidity slowly increased. After dripping, warm up naturally and stir for 12 hours.The ice water bath was cooled to 0-5 C and diluted with 600 mL of DCM. The prepared Na2S2O3 aqueous solution (consisting of Na2S2O3161.5 g, 2.6 eq and water 600 mL) was added dropwise.Keep stirring for 2h until the system is clear. Dispense liquid, combine organic phase, cool to 0-2C,A solution consisting of NaHCO3 (26 g) and water (120 mL) was added dropwise.Adjust pH=8, stir for 15 min, and let stand for 15 min. Phase,The organic phase was stirred with acetic acid (160 mg, 10 drops) and acidified to pH=5-6. The product had an HPLC purity of 86% and the product went directly to the next step.

References: [1]Patent: CN110256385,2019,A .Location in patent: Paragraph 0059-0091.
[2]Tetrahedron Letters,1991,vol. 32,p. 1553 - 1556.
[3]Journal of the Chemical Society. Perkin transactions I,1988,p. 2821 - 2826.
[4]Journal of Medicinal Chemistry,1993,vol. 36,p. 243 - 248.
[5]Journal of Medicinal Chemistry,1989,vol. 32,p. 256 - 264.
[6]Patent: US2006/41016,2006,A1 .Location in patent: Page/Page column 4.
[7]Patent: US2009/163596,2009,A1 .Location in patent: Page/Page column 10.
[8]Patent: WO2010/109476,2010,A2 .Location in patent: Page/Page column 13.
[9]Patent: WO2011/46569,2011,A1 .Location in patent: Page/Page column 61-62.
[10]Patent: WO2013/93528,2013,A1 .Location in patent: Page/Page column 9-12.
[11]Patent: WO2013/164729,2013,A1 .Location in patent: Page/Page column 27.
[12]Chirality,2015,vol. 27,p. 392 - 396.
[13]Patent: CN107973767,2018,A .Location in patent: Paragraph 0043; 0044; 0045; 0046; 0047; 0048.

3
[ 31752-99-5 ]
[ 65025-95-8 ]

References: [1]Collection of Czechoslovak Chemical Communications,1997,vol. 62,p. 1325 - 1341.

4
[ 31752-99-5 ]
[ 58707-50-9 ]

References: [1]Collection of Czechoslovak Chemical Communications,1997,vol. 62,p. 1325 - 1341.

5
[ 31752-99-5 ]
[ 84172-57-6 ]

References: [1]Collection of Czechoslovak Chemical Communications,1997,vol. 62,p. 1325 - 1341.

6
[ 31752-99-5 ]
[ 65025-96-9 ]

References: [1]Collection of Czechoslovak Chemical Communications,1997,vol. 62,p. 1325 - 1341.

7
[ 31752-99-5 ]
[ 58707-52-1 ]

References: [1]Collection of Czechoslovak Chemical Communications,1997,vol. 62,p. 1325 - 1341.

8
[ 31752-99-5 ]
[ 67788-45-8 ]

References: [1]Collection of Czechoslovak Chemical Communications,1997,vol. 62,p. 1325 - 1341.
[2]Collection of Czechoslovak Chemical Communications,1997,vol. 62,p. 1325 - 1341.

9
[ 31752-99-5 ]
[ 59122-48-4 ]

References: [1]Collection of Czechoslovak Chemical Communications,1997,vol. 62,p. 1325 - 1341.

10
[ 31752-99-5 ]
[ 58682-80-7 ]

References: [1]Collection of Czechoslovak Chemical Communications,1997,vol. 62,p. 1325 - 1341.

11
[ 31752-99-5 ]
7-((1R,2S,3R,5S)-5-Acetoxy-3-hydroxy-2-hydroxymethyl-cyclopentyl)-heptanoic acid methyl ester [ No CAS ]

References: [1]Collection of Czechoslovak Chemical Communications,1997,vol. 62,p. 1325 - 1341.

12
[ 31752-99-5 ]
[ 62137-77-3 ]

References: [1]Collection of Czechoslovak Chemical Communications,1997,vol. 62,p. 1325 - 1341.

13
[ 31752-99-5 ]
[ 61302-47-4 ]

References: [1]Collection of Czechoslovak Chemical Communications,1997,vol. 62,p. 1325 - 1341.

14
[ 31752-99-5 ]
[ 61302-48-5 ]

References: [1]Collection of Czechoslovak Chemical Communications,1997,vol. 62,p. 1325 - 1341.

15
[ 31752-99-5 ]
7-[(1R,2R,3R,5S)-5-Hydroxy-2-((E)-4-hydroxy-4-methyl-oct-1-enyl)-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-heptanoic acid methyl ester [ No CAS ]

References: [1]Collection of Czechoslovak Chemical Communications,1997,vol. 62,p. 1325 - 1341.

16
[ 31752-99-5 ]
7-[(1R,2R,3R)-2-((E)-4-Hydroxy-4-methyl-oct-1-enyl)-5-oxo-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-heptanoic acid methyl ester [ No CAS ]

References: [1]Collection of Czechoslovak Chemical Communications,1997,vol. 62,p. 1325 - 1341.

17
[ 31752-99-5 ]
[ 197523-79-8 ]

References: [1]Collection of Czechoslovak Chemical Communications,1997,vol. 62,p. 1325 - 1341.

18
[ 31752-99-5 ]
7-[(1R,2R,3R,5S)-5-Acetoxy-2-((E)-4-hydroxy-4-methyl-oct-1-enyl)-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-heptanoic acid methyl ester [ No CAS ]

References: [1]Collection of Czechoslovak Chemical Communications,1997,vol. 62,p. 1325 - 1341.
[2]Collection of Czechoslovak Chemical Communications,1997,vol. 62,p. 1325 - 1341.

19
[ 31752-99-5 ]
7-[(1R,2R,3R,5S)-5-Acetoxy-2-((E)-4-hydroxy-4-methyl-oct-1-enyl)-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-heptanoic acid butyl ester [ No CAS ]

References: [1]Collection of Czechoslovak Chemical Communications,1997,vol. 62,p. 1325 - 1341.

20
[ 31752-99-5 ]
(3aR,4S,5R,6aR)-2-(dichloromethylene)-4-<(2,2-dimethyl-1-oxopropoxy)methyl>hexahydro-2H-cyclopenta<b>furan-5-yl 1,1'-biphenyl-4-carboxylate [ No CAS ]

References: [1]Journal of Organic Chemistry,1994,vol. 59,p. 5752 - 5757.

21
[ 31752-99-5 ]
[ 117625-46-4 ]