88112-35-0

Basic information

• Product Name: (-)-8-phenylmenthyl (2S,3R)-2-hydroxy-3-methyl-4-pentenoate
• CAS NO: 88112-35-0
• Molecular Weight: 344.494
• Mol File: 88112-35-0.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (-)-8-phenylmenthyl (2S,3R)-2-hydroxy-3-methyl-4-pentenoate(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-8-phenylmenthyl (2S,3R)-2-hydroxy-3-methyl-4-pentenoate(88112-35-0)
• EPA Substance Registry System: (-)-8-phenylmenthyl (2S,3R)-2-hydroxy-3-methyl-4-pentenoate(88112-35-0)

Safety Data

• Hazardous Substances Data: 88112-35-0(Hazardous Substances Data)

Upstream product

• 17486-13-4 (Z)-crotyltrimethylsilane 
• 84312-20-9 (1R,3R,4S)-8-phenylmenthyl glyoxylate 
• 17486-12-3 (E)-but-2-en-1-yltrimethylsilane 
• 35998-93-7 tri-n-butylcrotyltin 
• 65253-04-5 (-)-8-phenylmenthol 
• 72526-00-2 (-)-8-phenylmenthyl acrylate 
• 89-82-7 pulegone 
• 3200-73-5 trans-2-butenyltrimethylstannane 
• 104197-95-7 (1R,2S,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexyl nitrooxyacetate 
• 76371-55-6 9-But-2-enyl-9-borabicyclo<3.3.1>nonane 
• 97371-54-5 (-)-(2S,5R)-5-Methyl-2-(1-methyl-1-phenylethyl)cyclohexanon 
• 80595-59-1 bromoacetic acid (-)-8-phenylmenthol ester 
• 109385-09-3 [((E)-But-2-enyl)oxy]-acetic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 

Relevant articles and documents

Enantio- and Diastereo-selective Reaction of But-2-enylstannane with Glyoxylate Esters and its Application to a Short Synthesis of Verrucarinolactone

The erythro-3-alkyl-2-hydroxypropionate unit in (4) is predominantly obtained via the reaction of but-2-enylstannane (2a) with glyoxylate esters (3) while the threo-isomer (5) is preferentially produced via 9-but-2-enyl-9-borabicyclononane (2b); the former reaction has been applied to the enantioselective synthesis of verrucarinolactone (6).

ASYMMETRIC INDUCTION IN THE ENE REACTION OF GLYOXYLATE ESTERS OF 8-PHENYLMENTHOL

We recently communicated (J.K.Whitesell, A.Bhattacharya, D.A.Aguilar and K.Henke, J.Chem.Soc.Chem.Commun. 989 (1982)) a highly efficient and effective method for the control of absolute stereochemistry through asymmetric induction in the ene reaction the chiral glyoxylate 1 with alkenes.We now have accumulated sufficient information on this process in terms of both its mechanistic details as well as its scope and applicability to a variety of situations that warrants a more complete presentation of these reactions.

Further Synthesis of Optically Active Verrucarinic Acid

Two new syntheses of verrucarinic acid ((2S,3R)-2,5-dihydroxy-3-methylpentanoic acid) and its derivatives, suitably protected for the further conversion to macrocyclic trichothecenes, are described.The first one makes use of a diastereoselective alkylation of a (-)-(S)-malic acid ester and the regioselective reduction of one carboxyl function to a methyl group.The second approach involves a stereoselective addition of an allylsilane to a chiral glyoxylate.