61305-35-9

Basic information

• Product Name: (4R)-(+)-T-BUTYLDIMETHYLSILOXY-2-CYCLOPENTEN-1-ONE
• Synonyms: (R)-4-TERT-BUTYLDIMETHYLSILYLOXY-2-CYCLO-PENTEN-1-ONE;(R)-4-(TERT-BUTYL-DIMETHYLSILYLOXY)CYCLOPENT-2-ENONE;(4R)-(+)-T-BUTYLDIMETHYLSILOXY-2-CYCLOPENTEN-1-ONE;(R)-4-Tert-butyldimethylsilyloxy-2-cyclo-penten-1-one(e.e.);(R)-4-tert-Butyldimethylsilyloxy-2-cyclopenten-1-one,95%,98% ee
• CAS NO: 61305-35-9
• Molecular Formula: C₁₁H₂₀O₂Si
• Molecular Weight: 212.36
• Product Categories: pharmacetical
• Mol File: 61305-35-9.mol
• Article Data: 5

Chemical Properties

• Melting Point: 26-28 °C
• Boiling Point: 246.1 °C at 760 mmHg
• Flash Point: 85.4 °C
• Appearance: /
• Density: 0.94 g/cm³
• Vapor Pressure: 0.0276mmHg at 25°C
• Refractive Index: 1.458
• CAS DataBase Reference: (4R)-(+)-T-BUTYLDIMETHYLSILOXY-2-CYCLOPENTEN-1-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: (4R)-(+)-T-BUTYLDIMETHYLSILOXY-2-CYCLOPENTEN-1-ONE(61305-35-9)
• EPA Substance Registry System: (4R)-(+)-T-BUTYLDIMETHYLSILOXY-2-CYCLOPENTEN-1-ONE(61305-35-9)

Safety Data

• Hazard Codes: Xn:Harmful
• Statements: R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
• Safety Statements: S36/37:Wear suitable protective clothing and gloves.
• Hazardous Substances Data: 61305-35-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H20O2Si/c1-11(2,3)14(4,5)13-10-7-6-9(12)8-10/h6-7,10H,8H2,1-5H3/t10-/m0/s1

Upstream product

• 59995-47-0 4-Hydroxycyclopent-2-enone 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 69739-34-0 t-butyldimethylsiyl triflate 
• 61305-35-9 4-[(tert-butyldimethylsilyl)oxy]cyclopent-2-enone 
• 98-80-6 phenylboronic acid 
• 59995-48-1 (R)-4-acetoxycyclopent-2-en-1-one 
• 1391630-27-5 (+/-)-4-oxocyclopenten-2-enyl 2-phenylacetate 

Downstream Products

• 98892-00-3 2-(1-phenylseleno-2-hydroxyethyl)-3-<(3S)-(E)-tertbutyldimethylsilyloxy-1-octenyl>-4(R)-tert-butyldimethylsilyloxycyclopentanone 
• 153868-71-4 tert-Butyl <(1S,5R)-2-oxo-5-phenylcyclopent-3-en-1-yl>acetate 
• 153868-69-0 tert-Butyl <(1S,4S,5R)-4-(tert-butyldimethylsiloxy)-2-oxo-5-phenylcyclopent-1-yl>acetate 
• 114738-30-6 (3R^*,4S^*)-3-<(tert-butyldimethylsilyl)oxy>-4-phenylcyclopentan-1-one 
• 61305-30-4 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (1R,4S)-4-(tert-butyl-dimethyl-silanyloxy)-cyclopent-2-enyl ester 
• 61305-30-4 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (1S,4R)-4-(tert-butyl-dimethyl-silanyloxy)-cyclopent-2-enyl ester 
• 885612-75-9 (3S,4S)-3-(benzylthio)-4-(tert-butyldimethylsilyloxy)cyclopentan-1-one 
• 1369917-07-6 7-hydroxy-11,15-bis-O-(tert-butyldimethylsilyl)-16-(3-methoxymethyl)phenyl-ω-tetranor-PGE1 methyl ester 
• 1369916-93-7 (7E)-7,8-didehydro-16-(3-methoxymethyl)phenyl-ω-tetranor-PGE1 
• 1369917-08-7 (7E)-7,8-didehydro-11,15-bis-O-(tert-butyldimethylsilyl)-16-(3-methoxymethyl)phenyl-ω-tetranor-PGE1 methyl ester 
• 1369917-11-2 (7E)-7,8-didehydro-16-(3-methoxymethyl)phenyl-ω-tetranor-PGE1 methyl ester 
• 56745-67-6 (4S)-4-tert-butyldimethylsilyloxycyclopent-2-en-1-one 

Relevant articles and documents

Pseudo enantiomeric carbohydrate olefin ligands - Case study and application in kinetic resolution in rhodium(I)-catalysed 1,4-addition

In order to investigate significant differences in asymmetric induction for pseudo enantiomeric carbohydrate olefin ligands in rhodium(I)-catalysed 1,4-addition reactions, we designed a set of new olefin ligands differing in relative configuration and pyranoside conformation. With these, we have successfully elucidated structural requirements for metal binding and also identified an improved alternative for one pseudo enantiomer. Furthermore, we report the efficient kinetic resolution of a racemic 4-hydroxycyclopentenone derivative by 1,4-addition.

Toward the total syntheses of pepluanin A and euphosalicin: Concise route to a highly oxygenated cyclopentane as a common intermediate

A substrate controlled asymmetric synthesis is described of a highly functionalized cyclopentanyl vinyl triflate which serves as an advanced intermediate in the total synthesis of the novel multidrug resistance reversing jatrophanes pepluanin A and euphosalicin. Key steps are a Claisen-Eschenmoser rearrangement followed by hydroxy-lactonization, intramolecular trans-lactonization, Davis hydroxylation and regioselective enoltriflate formation.

Kinetic Resolution of Racemic Allylic Alcohols by BINAP-Ruthenium(II)-Catalyzed Hydrogenation

Chiral allylic secondary alcohols have been resolved efficiently by homogeneous hydrogenation catalyzed by (R)- or (S)-BINAP-Ru diacetate complex.The combined effects of intramolecular and intermolecular asymmetric induction give up to 76:1 differentiation between the enantiomeric unsaturated alcohols.