99877-51-7

Basic information

• Product Name: (1R,2S,3R)-3-(5-hydroxypent-1-en-2-yl)-1,2-dimethylcyclopentanol
• CAS NO: 99877-51-7
• Molecular Formula: C₁₂H₂₂O₂
• Molecular Weight: 198.3019
• Mol File: 99877-51-7.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 312.4°C at 760 mmHg
• Flash Point: 142.8°C
• Density: 0.99g/cm³
• Vapor Pressure: 4.66E-05mmHg at 25°C
• Refractive Index: 1.492
• CAS DataBase Reference: (1R,2S,3R)-3-(5-hydroxypent-1-en-2-yl)-1,2-dimethylcyclopentanol(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2S,3R)-3-(5-hydroxypent-1-en-2-yl)-1,2-dimethylcyclopentanol(99877-51-7)
• EPA Substance Registry System: (1R,2S,3R)-3-(5-hydroxypent-1-en-2-yl)-1,2-dimethylcyclopentanol(99877-51-7)

Safety Data

• Hazardous Substances Data: 99877-51-7(Hazardous Substances Data)

Upstream product

• 122091-59-2 (4R,1'S,2'S,3'R)-5-hydroxy-4-(3'-hydroxy-2',3'-dimethylcyclopentyl)pentyl pivalate 
• 109908-46-5 (2S,3R)-3-(4-Hydroxy-1-methylene-butyl)-2-methyl-cyclopentanone 
• 75-16-1 methylmagnesium bromide 
• 119987-24-5 (2S,3R)-3-[4-(tert-Butyl-dimethyl-silanyloxy)-1-methylene-butyl]-2-methyl-cyclopentanone 
• 109908-47-6 Toluene-4-sulfonic acid 5-(tert-butyl-dimethyl-silanyloxy)-2-((6S,7S)-6-methyl-1,4-dioxa-spiro[4.4]non-7-yl)-pentyl ester 
• 109908-42-1 ((6S,7S)-6-Methyl-1,4-dioxa-spiro[4.4]non-7-yl)-acetonitrile 
• 109908-40-9 (2S,3S)-2-methyl-3(bromomethyl)cyclopentanone 
• 109908-41-0 (6S,7R)-7-Bromomethyl-6-methyl-1,4-dioxa-spiro[4.4]nonane 
• 122058-47-3 (4R,1'S,2'S,3'R)-4-(3'-hydroxy-2',3'-dimethylcyclopentyl)-5-(methanesulfonyloxy)pentyl pivalate 
• 122091-65-0 2,2-Dimethyl-propionic acid (S)-4-((1S,2S,3R)-3-hydroxy-2,3-dimethyl-cyclopentyl)-hex-5-enyl ester 
• 122058-41-7 Methanesulfonic acid (S)-3-((1S,2S,3R)-3-hydroxy-2,3-dimethyl-cyclopentyl)-pent-4-enyl ester 
• 144491-35-0 2,2-Dimethyl-propionic acid (R)-4-((1R,2S,3R)-3-hydroxy-2,3-dimethyl-cyclopentyl)-5-iodo-pentyl ester 
• 122091-58-1 (3S,1'S,2'S,3'R)-methyl 3-(3'-hydroxy-2',3'-dimethylcyclopentyl)pent-4-enoate 
• 122091-62-7 (S)-4-((1S,2S,3R)-3-Hydroxy-2,3-dimethyl-cyclopentyl)-hex-5-enenitrile 

Downstream Products

• 121979-32-6 chokol F 
• 144426-65-3 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid 4-((1R,2S,3R)-3-hydroxy-2,3-dimethyl-cyclopentyl)-pent-4-enyl ester 

Relevant articles and documents

Enantioselective Route to (-)-Chokol A

Stereoselective introduction of a methyl group to (3R)-2-methylcyclopentanone (2), followed by orthoester Claisen rearrangement provided the methyl ester (6) leading to (-)-chokol A (4).

A Short Synthesis of (-)-Chokol A

(-)-Chokol A (10) was prepared in six steps (22 percent overall yield) via conjugate addition of a higher order cyanocuprate to the chiral 2-oxo-cyclopentenecarboxylate 2n.After deprotection by transesterification the enantiomerically pure β-ketoester 5 was obtained which was transformed by α-methylation and subsequent decarbethoxylation to the cyclopentanone derivative 8.Addition of methylcerium dichloride resulted in a mixture of 9a, 9b and 9c (78:16:6), from which the main diastereomer 9a was separated by MPLC.Finally desilylation of 9a achieved (-)-chokol A (10).

Efficient Chemical Conversion of (+/-)-Chokol G to (+/-)-Chokols A, B, C, F, and K, Chokolic Acid B, and Chokolal A

Fungitoxic sesquiterpenoid chokols A, B, C, F, and K, chokolic acid B, and chokolal A were synthesized from chokol G by modifying the side chain.