38484-55-8

Basic information

• Product Name: (2S,5R)-2,5-Hexanediol
• Synonyms: (2R,5S)-2,5-Hexanediol;(2S,5R)-2,5-Hexanediol;(2S,5R)-Hexane-2,5-diol;meso-2,5-Hexanediol
• CAS NO: 38484-55-8
• Molecular Formula: C₆H₁₄O₂
• Molecular Weight: 0
• Mol File: 38484-55-8.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (2S,5R)-2,5-Hexanediol(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,5R)-2,5-Hexanediol(38484-55-8)
• EPA Substance Registry System: (2S,5R)-2,5-Hexanediol(38484-55-8)

Safety Data

• Hazardous Substances Data: 38484-55-8(Hazardous Substances Data)

Upstream product

• 18545-25-0 5-methyl-tetrahydro-furan-2-ol 
• 18006-13-8 methyltriisopropoxytitanium(IV) 
• 5194-50-3 (E,Z)-2,4-hexadiene 
• 110-13-4 2,5-hexanedione 
• 3031-66-1 3-hexyn-2,5-diol 

Downstream Products

• 17397-24-9 hex-5-en-2-ol 
• 33447-90-4 meso-2,5-hexanediol dimethanesulfonate 
• 65709-73-1 (5R)-hydroxyhexane-2-one 

Relevant articles and documents

Biocatalytical production of (5S)-hydroxy-2-hexanone

Biocatalytical approaches have been investigated in order to improve accessibility of the bifunctional chiral building block (5S)-hydroxy-2-hexanone ((S)-2). As a result, a new synthetic route starting from 2,5-hexanedione (1) was developed for (S)-2, whi

Asymmetric hydrosilylation of ketones using trans-chelating chiral peralkylbisphosphine ligands bearing primary alkyl substituents on phosphorus atoms

Asymmetric hydrosilylation of simple ketones with diphenylsilane proceeded at -40 °C in the presence of a rhodium complex (0.001 - 0.01 molar amount) coordinated with a trans-chelating chiral bisphosphine ligand bearing linear alkyl substituents on the phosphorus atoms, (R,R)-(S,S)-Et-, Pr-, or BuTRAP, giving the corresponding optically active (S)- secondary alcohols with up to 97% ee. The asymmetric hydrosilylation using TRAP ligands with bulkier P-substituents resulted in much lower enantioselectivities. The EtTRAP-rhodium catalyst was also effective for asymmetric hydrosilylation of keto esters with a coordination site for a rhodium atom (up to 98% ee). Optically active symmetrical diols were obtained with up to 99% ee from the corresponding diketones via the asymmetric reduction using 2.5 molar amounts of diphenylsilane.

Oxazaborolidine-catalysed reduction of alk-2-ene-1,4-diones. A convenient access to chiral 1,4-diols

An efficient method for the preparation of C2-symmetric, chiral alk-2- ene-1,4-diols (4) has been achieved, based on the borane-mediated reduction of symmetric alk-2-ene-1,4-diones (2) in the presence of oxazaborolidine (R)- 1. In general, the presence of the double bond in 2 has been beneficial (compared with the related saturated 1,4-diketones 3) not only as far as the stereoselectivity in the reduction step is concerned, but also because it allowed us to remove meso-4 by chomatography and/or to improve the stereochemical purity of several resulting mixtures of diols 4 by Sharpless' epoxidation. Enantioenricbed compounds 4 have been readily reduced to saturated diols with negligible loss of optical purity.

Stereoselective reduction of unsaturated 1,4-diketones. A practical route to chiral 1,4-diols

A new synthetic route to C2-symmetric chiral 1,4-diols based on the borane-mediated oxazaborolidine-catalysed reduction of 2-ene-1,4-diones (2), of 2-yne-1,4-diones (3), and/or of Co-complexed diketones 4 is described. Good to excellent enantio- and diastereoselectivities have been obtained in the reduction of diketones 3 and 4, catalysed by oxazaborolidines 6 and 5, respectively.

Yeast-mediated synthesis of optically active diols with C2-symmetry and (R)-4-pentanolide

Reduction of some diketones and a keteacid with yeast, Pichia farinosa IAM 4682 was examined. The reduction of carbonyl groups proceeded highly selectively with an anti-Prelog fashion to give (R)-alcohols. (2R,5R)2,5- Hexanediol (83% yd., >99% e.e., 95% d.e.), (2R,4R)-2,4-pentanediol (94% yd., >99% e.e., 98% d.e.), and (R)-4-pentanolide (67% yd., >99% e.e.) were highly efficiently obtained from the corresponding ketones. Effect of the structure of substrate on the stereochemical course as well as the selectivity were discussed.

Asymmetric Hydrosilylation of Symmetrical Diketones Catalyzed by a Rhodium Complex with Trans-Chelating Chiral Diphosphine EtTRAP

Asymmetric hydrosilylation of symmetrical diketones with diphenylsilane in the presence of catalytic amount (/ = 100> of rhodium complex coordinated with trans-chelating chiral phosphine ligand EtTRAP gave corresponding optically active symmetrical diols with high enantiomeric excesses.

Lactols in Stereoselection 1. Highly selective 1,4- and 1,5-Asymmetric Induction

Nucleophilic addition to substituted γ- and δ-lactols with titanium reagents provides 1,4-syn and 1,5-syn diols in high stereoselectivity, which represents a new and simple method for the remote asymmetric induction.

-CYCLOADDITION OF SINGLET OXYGEN TO CONJUGATED ACYCLIC HEXADIENES : EVIDENCE OF SINGLET OXYGEN INDUCED cistrans-ISOMERIZATION

Addition of singlet oxygen to trans,trans-2,4-hexadiene (1) occurs stereospecifically to give endoperoxide 2.With cis,trans-2,4-hexadiene (4), however, a mixture of diastereomeric endoperoxides, 2 + 5, is observed.Evidence of a singlet oxygen - induced cistrans - isomerization is gained by competitive Diels-Alder reaction of 4 with singlet oxygen/diethyl diazenedicarboxylate.