84786-80-1

Basic information

• Product Name: (3aR,4S,5R,6aS)-4-(tert-Butyldiphenylsilyloxy)methyl-5-hydroxy-hexahydro-2H-cyclopenta[b]furan-2-one
• Synonyms: (3aR,4S,5R,6aS)-4-(tert-Butyldiphenylsilyloxy)methyl-5-hydroxy-hexahydro-2H-cyclopenta[b]furan-2-one;(3aR,4S,5R,6aS)-4-[[[(1,1-DiMethylethyl)diphenylsilyl]oxy]Methyl]hexahydro-5-hydroxy-2H-cyclopenta[b]furan-2-one
• CAS NO: 84786-80-1
• Molecular Formula: C₂₄H₃₀O₄Si
• Molecular Weight: 410.5781
• Product Categories: Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 84786-80-1.mol

Chemical Properties

• Melting Point: 90-91 °C
• Boiling Point: 520.7±46.0 °C(Predicted)
• Appearance: /
• Density: 1.16±0.1 g/cm3(Predicted)
• Solubility: Acetone, Chloroform, Dichloromethane, Ethyl Acetate, Methanol
• PKA: 14.30±0.40(Predicted)
• CAS DataBase Reference: (3aR,4S,5R,6aS)-4-(tert-Butyldiphenylsilyloxy)methyl-5-hydroxy-hexahydro-2H-cyclopenta[b]furan-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (3aR,4S,5R,6aS)-4-(tert-Butyldiphenylsilyloxy)methyl-5-hydroxy-hexahydro-2H-cyclopenta[b]furan-2-one(84786-80-1)
• EPA Substance Registry System: (3aR,4S,5R,6aS)-4-(tert-Butyldiphenylsilyloxy)methyl-5-hydroxy-hexahydro-2H-cyclopenta[b]furan-2-one(84786-80-1)

Safety Data

• Hazardous Substances Data: 84786-80-1(Hazardous Substances Data)

Upstream product

• 130386-85-5 (3aR,4S,5R,6aS)-5-benzoyloxy-4-[(t-butyldiphenylsiloxy)methyl]hexahydro-2H-cyclopenta[b]furan-2-one 
• 84786-90-3 Acetic acid (3aR,4S,5R,6aS)-4-(tert-butyl-diphenyl-silanyloxymethyl)-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester 
• 32233-40-2 (3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 26054-65-9 (1S,5R,6R,7R)-(-)-2-oxa-6-(hydroxymethyl)-7-acetoxybicyclo<3.3.0>-octan-3-one 
• 56487-71-9 (3aα,4α,5β,6aα)-(-)-5-acetoxyhexahydro-4-(methoxymethyl)-2H-cyclopentafuran-2-one 
• 136235-73-9 (2R,3S)-5-tert-butyldimethylsilyloxy-2,3-epoxypentan-1-ol 
• 39746-00-4 (1S,5R,6S,7R)-7-benzoyloxy-6-hydroxymethyl-2-oxabicyclo[3.3.0]octan-3-one 
• 315716-34-8 (1S,2S,6R,8S)-10,10-dimethyl-5,9,11-trioxatricyclo[6.4.0.0^2,6]dodecan-4-one 
• 315716-28-0 (1S,2S,6R,8S)-10,10-dimethyl-5,9,11-trioxatricyclo[6.4.0.0^2,6]dodecan-4-ol 
• 377778-93-3 5-((tert-butyldimethylsilyl)oxy)pent-2-en-1-ol 
• 193476-15-2 methyl (2E)-2-[(1S,2R)-tert-butyldimethylsilyloxyethyl-4,4-dimethyl-3,5-dioxacyclohexyl]2-propenoate 
• 193476-16-3 (2E)-3-[(1S,2R)-2-(2-tert-butyldimethylsilyloxyethyl)-4,4-dimethyl-3,5-dioxacyclohexyl]-2-propen-1-ol 
• 193476-17-4 (4R,5S)-4-{5-[(1E)-1,3-butadienyl]}-4-(2-tert-butyldimethylsilyloxyethyl)-2,2-dimethyl-1,3-dioxa-cyclohexane 

Downstream Products

• 84786-91-4 (3aS,4R,6aR)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-tetrahydro-cyclopenta[b]furan-2,5-dione 
• 208114-21-0 (3aR,4S,5S,6aS)-4-[(t-butyldiphenylsiloxy)methyl]-5-fluorohexahydro-2H-cyclopenta[b]furan-2-one 
• 143572-29-6 (1S,4S,5S)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-5-hydroxymethyl-cyclopent-2-enol 
• 143572-25-2 (3aR,4S,6aS)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-3,3a,4,6a-tetrahydro-cyclopenta[b]furan-2-one 
• 143572-28-5 Formic acid (1S,4S,5R)-4-(tert-butyl-diphenyl-silanyloxymethyl)-5-formyl-cyclopent-2-enyl ester 
• 143572-27-4 (3aS,4S,6aS)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-3,3a,4,6a-tetrahydro-2H-cyclopenta[b]furan-2,3-diol 
• 143572-26-3 (3aS,4S,6aS)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-3-hydroxy-3,3a,4,6a-tetrahydro-cyclopenta[b]furan-2-one 
• 143572-30-9 (1S,4S,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-(tert-butyl-diphenyl-silanyloxymethyl)-cyclopent-2-enol 
• 143572-31-0 9-[(1R,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-(tert-butyl-diphenyl-silanyloxymethyl)-cyclopent-2-enyl]-6-chloro-9H-purine 
• 143678-59-5 (1R,4S,5R)-9-(4,5-Bishydroxymethylcyclopent-2-en-1-yl)-9H-adenine 
• 1432425-91-6 C₃₄H₄₈O₄Si 

Relevant articles and documents

Synthesis and evaluation of 2,3-dinorprostaglandins: Dinor-PGD1 and 13-epi-dinor-PGD1 are peroxisome proliferator-activated receptor α/γ dual agonists

2,3-Dinorprostaglandins (dinor-PGs) have been regarded as β-oxidation products of arachidonic-acid-derived prostaglandins, but their biological activities in mammalian cells remain unclear. On the other hand, C18 polyunsaturated fatty acids (PUFAs), such

11-halo prostaglandins for the treatment of glaucoma or ocular hypertension

A method of treating glaucoma or ocular hypertension in a patient, which comprises administering to the patient a pharmaceutically effective amount of a compound of formula I:

15-ketal postaglandins for the treatment of glaucoma or ocular hypertension

A method of treating glaucoma or ocular hypertension in a patient, which comprises administering to the patient a pharmaceutically effective amount of a compound of formula I:

Total synthesis of prostaglandin F(2α) using nickel-catalyzed stereoselective cyclization of 1,3-diene and tethered aldehyde via transmetalation of nickelacycle with diisobutylaluminum acetylacetonate

Total synthesis of prostaglandin F(2α) utilizing a nickel(0)-catalyzed cyclization of 1,3-diene and tethered aldehyde was achieved. The cyclization proceeded via a transmetalation of nickelacycle with dilsobutylaluminum acetylacetonate ((i)Bu2-ALAC). Thus, the reaction of 19, having a side chain corresponding to the α-chain in PGF(2α) with Ni(cod)2 (10 mol %), PPh3 (20 mol %), and 1,3-cyclohexadiene (25 mol %) in the presence of (i)Bu2-ALAC (1.5 eq) proceeded stereoselectively to give the cyclized product 26 in 54% yield. During the cyclization of 19, the Z-olefin at C-5 in the side chain completely retained its geometry, and the four contiguous chiral carbon centers in PGF(2α) were stereoselectively constructed. Transformation of the key intermediate 19 into PGF(2α) was successfully achieved.

AL-8810: A novel prostaglandin F(2α) analog with selective antagonist effects at the prostaglandin F(2α) (FP) receptor

A novel analog of prostaglandin F(2α) [AL-8810; (5Z, 13E)-(9S,11S,15R)- 9,15-dihydroxy-11-fluoro-15-(2-indanyl)-16,17, 18,19,20-pentanor-5,13- prostadienoic acid] has been discovered with uniquely low efficacy (E(max)) at the endogenous prostaglandin F(2α) receptors (FP receptors) of A7r5 rat thoracic aorta smooth muscle cells and Swiss mouse 3T3 fibroblasts, as assayed by stimulation of phospholipase C activity. AL-8810 has weak agonist potency (EC50) of 261 ± 44 nM (n = 3) and E(max) = 19% (relative to the full FP receptor agonist cloprostenol) in A7r5 cells and EC50 of 186 ± 63 nM (n = 3) and E(max) = 23% in 3T3 fibroblasts. AL-8810 exhibited properties of an apparent competitive antagonist, i.e., produced parallel dextral shifts of the agonist concentration-response curves and no significant suppression of the maximal agonist-induced response, when the potent, selective FP receptor agonist fluprostenol was used. The inhibition parameters of AL-8810 were: pA2 = 6.68 ± 0.23 and 6.34 ± 0.09 (n = 3-4) for A7r5 cells and 3T3 cells, respectively, with Schild slopes ranging from 0.80 to 0.92. AL-8810 concentration-dependently antagonized the response to 100 nM fluprostenol (K(i) = 426 ± 63 nM; n = 5) in A7r5 cells. However, even at 10 μM concentration, AL-8810 did not significantly inhibit functional responses of TP, DP, EP2, EP4, receptor subtypes in various cell lines. AL-8810 also did not antagonize the phospholipase C-coupled V1-vasopressin receptor in A7r5 cells. These results suggest that AL-8810 is a unique, selective antagonist at the FP receptor, a heretofore unavailable pharmacological tool that should be valuable for studying FP receptor-mediated functional responses in complex biological systems.

Synthesis of (1R, 4S, 5R)-9-(4,5-bishydroxy-methylcyclopent-2-en-1-yl)-9H-adenine [(-)-BCA] and selective inhibition of human immunodeficiency virus

(1R,4S,5R)-9(4,5-Bishydroxymethylcyclopent-2-en-1-yl)-9H-adenine [(-)-BCA] has been synthesized from (-)-Corey lactone in 11 steps and shown to have potent and selective effects against human immmunodeficiency virus type 1. The result demonstrated that th