58707-50-9

Basic information

• Product Name: (3aS,4R,5S,6aR)-hexahydro-5-hydroxy-4-(tert-butyldimethylsilyloxymethyl)-2H-cyclopenta[b]furan-2-one
• Synonyms: (3aS,4R,5S,6aR)-hexahydro-5-hydroxy-4-(tert-butyldimethylsilyloxymethyl)-2H-cyclopenta[b]furan-2-one
• CAS NO: 58707-50-9
• Molecular Weight: 286.444
• Mol File: 58707-50-9.mol

Chemical Properties

• CAS DataBase Reference: (3aS,4R,5S,6aR)-hexahydro-5-hydroxy-4-(tert-butyldimethylsilyloxymethyl)-2H-cyclopenta[b]furan-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (3aS,4R,5S,6aR)-hexahydro-5-hydroxy-4-(tert-butyldimethylsilyloxymethyl)-2H-cyclopenta[b]furan-2-one(58707-50-9)
• EPA Substance Registry System: (3aS,4R,5S,6aR)-hexahydro-5-hydroxy-4-(tert-butyldimethylsilyloxymethyl)-2H-cyclopenta[b]furan-2-one(58707-50-9)

Safety Data

• Hazardous Substances Data: 58707-50-9(Hazardous Substances Data)

Upstream product

• 62939-82-6 (3aR,4S,5R,6aS)-5-(acetyloxy)-4-[(acetyloxy)methyl]hexahydro-2H-cyclopenta[b]furan-2-one 
• 26054-46-6 (-)-(1S,5R)-2-oxabicyclo[3.3.0]oct-6-en-3-one 
• 54423-47-1 (+/-)-(3aα,4α,5β,6aα)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopentafuran-2-one 
• 67-56-1 methanol 
• 1381843-06-6 C₂₁H₃₄O₆Si 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 31752-99-5 (-)-Corey lactone 5-(4-phenylbenzoate) 
• 32233-40-2 (3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one 
• 165876-61-9 (3aR,4S,5R,6aS)-4-((tert-butyldimethylsilyloxy)methyl)-2-oxo hexahydro-2H-cyclopenta[b]furan-5-yl biphenyl-4-carboxylate 
• 72736-04-0 Acetic acid (3aS,4R,5S,6aR)-4-(tert-butyl-dimethyl-silanyloxymethyl)-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester 
• 65025-95-8 (3aR,4S,5R,6aS)-4-({[dimethyl(2-methyl-2-propanyl)silyl]oxy}methyl)-5-(tetrahydro-2H-pyran-2-yloxy)hexahydro-2H-cyclopenta[b]furan-2-one 

Downstream Products

• 1431141-69-3 (1S,2R,3R,4S)-2-(2-hydroxyethyl)-3-(hydroxymethyl)-4-(4-phenyl-1H-1,2,3-triazol-1-yl)cyclopentanol 
• 1431141-72-8 (1S,2R,3S,4R)-4-(tert-butyldimethylsilyloxy)-2-(2-(tert-butyldimethylsilyloxy)ethyl)-3-((tert-butyldimethylsilyloxy)methyl)cyclopentyl4-methylbenzenesulfonate 
• 1431141-74-0 (1R,2S,3R,4R)-3-(2-hydroxyethyl)-2-(hydroxymethyl)-4-(4-phenyl-1H-1,2,3-triazol-1-yl)cyclopentanol 
• 1431141-67-1 (1R,2S,3R,4S)-4-(tert-butyldimethylsilyloxy)-3-(2-(tert-butyldimethylsilyloxy)ethyl)-2-((tert-butyldimethylsilyloxy)methyl)cyclopentyl-4-methylbenzenesulfonate 
• 39746-00-4 (1S,5R,6S,7R)-7-benzoyloxy-6-hydroxymethyl-2-oxabicyclo[3.3.0]octan-3-one 
• 1354714-74-1 (3aS,4R,5S,6aR)-hexahydro-5-(tert-butyldiphenylsilyloxy)-4-(tert-butyldimethylsilyloxymethyl)-2H-cyclopentafuran-2-one 
• 1354714-75-2 (3aS,4R,5S,6aR)-hexahydro-5-benzoyloxy-4-(tert-butyldimethylsilyloxymethyl)-2H-cyclopenta[b]furan-2-one 
• 64982-35-0 (3aS,4R,5S,6aR)-hexahydro-5-(biphenyl-4-formyloxy)-4-(tert-butyldimethylsilyloxy methyl)-2H-cyclopenta[b]furan-2-one 
• 197523-93-6 (Z)-7-[(1S,2R,3S,5R)-5-Acetoxy-2-hydroxymethyl-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hept-5-enoic acid methyl ester 
• 333963-40-9 lubiprostone 
• 876068-08-5 7-[(1R,2R,3R)-2-(4,4-difluoro-3-oxooctyl)-5-oxo-3-(2-tetrahydropyranyloxy)cyclopentyl]heptanoic acid 
• 69222-61-3 2-oxo-6-syn-(hydroxymethyl)-7-anti-(tetrahydropyran-2-yloxy)-cis-bicyclo<3.3.0>octan-3-one 
• 31752-99-5 (-)-Corey lactone 5-(4-phenylbenzoate) 
• 165876-61-9 (3aR,4S,5R,6aS)-4-((tert-butyldimethylsilyloxy)methyl)-2-oxo hexahydro-2H-cyclopenta[b]furan-5-yl biphenyl-4-carboxylate 

Relevant articles and documents

Photoinduced Deoxygenative Borylations of Aliphatic Alcohols

A photochemical method for converting aliphatic alcohols into boronic esters is described. Preactivation of the alcohol as a 2-iodophenyl-thionocarbonate enables a novel Barton–McCombie-type radical deoxygenation that proceeds efficiently with visible light irradiation and without the requirement for a photocatalyst, a radical initiator, or tin or silicon hydrides. The resultant alkyl radical is intercepted by bis(catecholato)diboron, furnishing boronic esters from a diverse range of structurally complex alcohols.

The preparation method of the ruby's forefront

The invention relates to a preparation method of lubiprostone, and concretely relates to a preparation method of highly pure lubiprostone represented by formula (I). The method comprises the steps of reducing an initial compound, oxidizing, and hydrolyzing in order to obtain a target compound. Compared with other methods, the method provided by the invention has the advantages of good process reappearance, simple operation, high yield, low cost, high purity of the above obtained product, suitableness for industrialized production, and very high economic benefit.

Ruby's forefront method for preparing or intermediates (by machine translation)

The invention discloses a novel method for preparing a lubiprostone midbody as shown in the formula 7. The method comprises the following steps: (1), a compound as shown in the formula 1 reacts with tert-butyldimethylsilyl chloride to selectively protect a primary hydroxyl group, thereby obtaining a compound shown in the formula 2; (2), a protecting group is applied to the compound 2 under the action of a catalyst, thereby obtaining a compound shown in the formula 3; (3), after the compound 3 is reduced through diisobutylaluminium hydride, a Wittig reaction is carried out on the compound 3, thereby obtaining carboxylic acid shown in the formula 4; (4), the compound 4 is protected in an acetonitrile solvent through a protecting group, thereby obtaining a compound shown in the formula 5; (5), the compound 5 is treated by using the tert-Butyldimethylsilane for removing the protecting group, thereby obtaining a compound shown in the formula 6; and (6), the compound 6 is oxidized by an oxidant and then reacts with a compound shown in the formula (10), thereby obtaining the higher-purity compound shown in the formula 7.

Transformation of δ-lactone in γ-lactone in the Corey route for synthesis of prostaglandins

(Un)substituted benzoate ester protected δ-lactone alcohols are alcoholized in acid catalysis in almost quantitative yield to hydroxyl-halogenoesters. For alkylesters the yield drops to ～70%. After changing the protection between primary and secondary alcohols, the intermediate halogenoesters are transformed into the known γ-lactone alcohols protected as ether, silyl-ether or trityl at the secondary alcohol group. Unprotected δ-lactone alcohol 1 is also quantitatively transformed in chloroester 20. After selective protection of the primary alcohol with bulky ether groups, this is finally transformed into the known Corey γ-lactone alcohol, protected as ester at the secondary alcohol.

Corey lactone as key precursor for a facile synthesis of novel 1,2,3-triazole carbocyclic nucleosides via Click Chemistry

Corey lactone (2) and Click Chemistry allowed for an efficient and facile approach to the synthesis of novel 1,2,3-triazole carbocyclic nucleosides (11 and 17) in good overall yields.

Efficient resolution of some monoprotected derivatives of Corey lactone

Racemic monoprotected at primary hydroxy group Corey lactones were resolved using (1S,2R,5R)-6,6-dimethyl-4-oxo-3-oxabicyclo-[3.1.0]hexan-2-ol as a chiral auxiliary reagent of hemiacylal chemotype.

Process for the synthesis of prostaglandins and intermediates thereof

A process is disclosed for the preparation of prostaglandins of the PGF2α-series, in particular Latanoprost, Bimatoprost and Travoprost, which are active in the treatment of ocular hypertensive conditions and glaucoma. The invention also relates to novel intermediates involved in the synthesis of these prostaglandin-PGF2α derivatives.

Silyl group deprotection by Pd/C/H2. A facile and selective method

An easy, high yield, RT, short-reaction-time Pd/C hydrogenation of silyl groups is described. This includes TES, TPS, TBS, TBDMS, TIPS, and TBDPS. The relative selectivity of the process has been investigated and we can show, for example, that TES, TPS, TBS, and TBDMS removal can be performed in the presence of TIPS and TBDPS.

Prostanoids: Synthesis of enantiomers of 15-deoxy-16-hydroxy-16-methylprostaglandin E1

Four optically pure isomers of methyl 11,16-dihydroxy-16-methyl-9-oxoprost-13-enoate (1a-1d) were synthesized using an approach reverse to the classical Corey procedure, the key intermediates being the easily accessible (-)- and (+)-enantiomers of the Corey lactone, 2a and 2b.

Prostanoids: LXVI. A priori Postulated "9-LO Prostanoids"

Based on the analysis of the literature data and the results given here, suggestions were made as to the pharmacological potential of "9-LO prostanoids." One representative of this class of compounds, (+)-2-decarboxy-2-ethyl-19,20-dinor-18-carboxyprostaglandin F2α, was synthesized starting from (-)-7α-hydroxy-6β-hydroxymethyl-cis-2-oxabicyclo[3.3.1]octan-3-one.