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
• Article Data: 14

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

• 58682-80-7 misoprostol 
• 62137-77-3 (Z)-7-[(1R,2R,3R,5S)-5-Acetoxy-2-hydroxymethyl-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hept-5-enoic acid methyl ester 
• 61302-47-4 methyl 7-((1R,2S,3R,5S)-5-acetoxy-2-hydroxymethyl-3-((tetrahydro-2H-pyran-2-yl)oxy)cyclopentyl)heptanoate 
• 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 
• 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 
• 1354714-74-1 (3aS,4R,5S,6aR)-hexahydro-5-(tert-butyldiphenylsilyloxy)-4-(tert-butyldimethylsilyloxymethyl)-2H-cyclopentafuran-2-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.

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.

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.