79413-88-0

Basic information

• Product Name: Toluene-4-sulfonic acid (1S,2S)-3-benzyloxy-2-hydroxy-1-methyl-propyl ester
• Synonyms: Toluene-4-sulfonic acid (1S,2S)-3-benzyloxy-2-hydroxy-1-methyl-propyl ester
• CAS NO: 79413-88-0
• Molecular Weight: 350.436
• Mol File: 79413-88-0.mol

Chemical Properties

• CAS DataBase Reference: Toluene-4-sulfonic acid (1S,2S)-3-benzyloxy-2-hydroxy-1-methyl-propyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Toluene-4-sulfonic acid (1S,2S)-3-benzyloxy-2-hydroxy-1-methyl-propyl ester(79413-88-0)
• EPA Substance Registry System: Toluene-4-sulfonic acid (1S,2S)-3-benzyloxy-2-hydroxy-1-methyl-propyl ester(79413-88-0)

Safety Data

• Hazardous Substances Data: 79413-88-0(Hazardous Substances Data)

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 85099-99-6 Benzoic acid (1S,2R)-3-benzyloxy-2-hydroxy-1-methyl-propyl ester 

Downstream Products

• 72229-17-5 (2S,3R)-2-[(benzyloxy)methyl]-3-methyloxirane 
• 72229-17-5 (S)-3-benzyloxymethyl-2,2-dimethyloxirane 

Relevant articles and documents

SYNTHESIS OF THE ENANTIOMERIC FORMS OF CIS AND TRANS 1-BENZYLOXY-2,3-EPOXY BUTANE AND OF (3S,4S) 4-METHYL-3-HEPTANOL

The C4 erythro and threo diols (7) and (8) are converted either into the chiral epoxides (13) and (15) or into the enantiomers (14) and (16); the epoxide (13) is used as chiral synthon for the preparation of (3S,4S) 4-methyl-3-heptanol (21).

Enantiomerically Pure Synthetic Building Blocks with Four C-Atoms and Two or Three Functional Groups from β-Hydroxy-butanoic, Malic, and Tartaric Acid

The pool of chiral, non-racemic electrophilic building blocks, which are available from simple natural products in both enantiomeric forms is enlarged by the epoxides 3, 5, and 10, by the tosylate 12a, and by the aldehydes 18 (cf. symbols A-D, 14, and Scheme 1).Key steps of the conversions leading from hydroxyacids to the building blocks are: epoxide-opening by triethylborohydride (1 --> 2a) and tosylate reduction (12a --> 12b); the Mitsunobu inversion (2a --> 4a); the reduction of (R,R)-tartaric ester to (R)-malic ester by NBS (N-bromosuccinimide) opening of the benzaldehyde acetal 8 and tin hydride reduction (6c -->7c); the enantiomer enrichment of optically active ethyl β-hydroxy-butanoate through the crystalline dinitrobenzoate 21b.Detailed procedures are given for large scale preparations of the key intermediates.The enantiomeric purities of the building blocks are secured by correlations.