574014-04-3

Basic information

• Product Name: (+)-(3S,4R)-[4-2H]-3-(p-toluenesulfonyloxy)chromane
• Synonyms: (+)-(3S,4R)-[4-2H]-3-(p-toluenesulfonyloxy)chromane
• CAS NO: 574014-04-3
• Molecular Weight: 305.359
• Mol File: 574014-04-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (+)-(3S,4R)-[4-2H]-3-(p-toluenesulfonyloxy)chromane(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-(3S,4R)-[4-2H]-3-(p-toluenesulfonyloxy)chromane(574014-04-3)
• EPA Substance Registry System: (+)-(3S,4R)-[4-2H]-3-(p-toluenesulfonyloxy)chromane(574014-04-3)

Safety Data

• Hazardous Substances Data: 574014-04-3(Hazardous Substances Data)

Upstream product

• 180469-87-8 (-)-(3R,4S)-Epoxychromane 
• 98-59-9 p-toluenesulfonyl chloride 
• 574014-02-1 (-)-(3S,4R)-[4-2H]-chroman-3-ol 

Downstream Products

• 1481-93-2 (S)-chroman-4-ol 
• 120523-16-2 (R)-4-chromanol 
• 491-37-2 2,3-dihydro-4H-1-benzopyran-4-one 

Relevant articles and documents

Stereochemical and mechanistic aspects of dioxygenase-catalysed benzylic hydroxylation of indene and chromane substrates

Toluene dioxygenase (TDO)-catalysed benzylic hydroxylation of indene substrates (8, 16 and 17), using whole cell cultures of Pseudomonas putida UV4, was found to yield inden-1-ol (14 and 223) and indan-1-one bioproducts (15 and 23). The formation of these bioproducts is consistent with the involvement of carbon-centred radical intermediates. TDO-catalysed oxidation of indenes 8 and 16 also gave cis-diols 13 and 18 respectively. TDO and naphthalene dioxygenase (NDO), used as both whole-cell preparation and as purified enzymes, were found to catalyse the benzylic hydroxylation of chromane 30, deuteriated (±)-chromane 30D and enantiomers (4S)-30D and (4R)-30D to yield (4R)- and (4S)-chroman-4-ols 31/31D respectively. The mechanism of benzylic hydroxylation of chromane 30/30D involves the stereoselective abstraction of a pro-R (with TDO) or a pro-S (with NDO) hydrogen atom at C-4 and a marked preference for retention of configuration.