91177-72-9

Basic information

• Product Name: (2S,3R)-heptane-2,3-diol
• Synonyms: (2S,3R)-heptane-2,3-diol
• CAS NO: 91177-72-9
• Molecular Weight: 132.203
• Mol File: 91177-72-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (2S,3R)-heptane-2,3-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3R)-heptane-2,3-diol(91177-72-9)
• EPA Substance Registry System: (2S,3R)-heptane-2,3-diol(91177-72-9)

Safety Data

• Hazardous Substances Data: 91177-72-9(Hazardous Substances Data)

Upstream product

• 96-04-8 2,3-heptanedione 

Downstream Products

• 624-22-6 (2S)-2-methyl-1-hexanol 
• 66050-98-4 (2R)-methyl-1-hexanol 

Relevant articles and documents

Assessing the stereoselectivity of: Serratia marcescens CECT 977 2,3-butanediol dehydrogenase

α-Hydroxy ketones and vicinal diols constitute well-known building blocks in organic synthesis. Here we describe one enzyme that enables the enantioselective synthesis of both building blocks starting from diketones. The enzyme 2,3-butanediol dehydrogenase (BudC) from S. marcescens CECT 977 belongs to the NADH-dependent metal-independent short-chain dehydrogenases/reductases family (SDR) and catalyses the selective asymmetric reductions of prochiral α-diketones to the corresponding α-hydroxy ketones and diols. BudC is highly active towards structurally diverse diketones in combination with nicotinamide cofactor regeneration systems. Aliphatic diketones, cyclic diketones and alkyl phenyl diketones are well accepted, whereas their derivatives possessing two bulky groups are not converted. In the reverse reaction vicinal diols are preferred over other substrates with hydroxy/keto groups in non-vicinal positions.

Regio- and stereoselective reduction of diketones and oxidation of diols by biocatalytic hydrogen transfer

The asymmetric reduction of symmetrical and nonsymmetrical diketones as well as the stereoselective oxidation of various diols by biocatalytic hydrogen transfer was investigated by employing lyophilized cells of Rhodococcus ruber DSM 44541 containing alcohol dehydrogense ADH-'A'. Symmetrical and nonsymmetrical diketones at the (ω-1)- and (ω-2)-positions are reduced to the Prelog product with high stereopreference, while sterically more demanding ketone moieties, for example those at the (ω-3)-position, remain unchanged. For the oxidation mode, differentiation between primary and secondary alcohols is achieved, and the (S)-configured secondary alcohols at the (ω-1)- and (ω-2)-positions are oxidized preferentially. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.