136030-28-9

Basic information

• Product Name: (2R,4R)-1,5-dichloropentane-2,4-diol
• Synonyms: (2R,4R)-1,5-dichloropentane-2,4-diol
• CAS NO: 136030-28-9
• Molecular Weight: 173.039
• Mol File: 136030-28-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2R,4R)-1,5-dichloropentane-2,4-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,4R)-1,5-dichloropentane-2,4-diol(136030-28-9)
• EPA Substance Registry System: (2R,4R)-1,5-dichloropentane-2,4-diol(136030-28-9)

Safety Data

• Hazardous Substances Data: 136030-28-9(Hazardous Substances Data)

Usage

General Description

"(2R,4R)-1,5-dichloropentane-2,4-diol" is a compound with the molecular formula C5H10Cl2O2. It is a diol, which means it contains two hydroxyl (-OH) groups. The "2R,4R" in its name indicates that it has two chiral centers, and the stereochemistry at each center is in the R configuration. (2R,4R)-1,5-dichloropentane-2,4-diol is a colorless liquid at room temperature and is slightly soluble in water. It is used in organic synthesis as a building block for the preparation of various pharmaceuticals, agrochemicals, and other fine chemicals. The presence of chlorine atoms and hydroxyl groups in "(2R,4R)-1,5-dichloropentane-2,4-diol" makes it a versatile compound for use in different chemical reactions.

Upstream product

• 591-51-5 phenyllithium 
• 209119-58-4 (4R,6R)-4,6-Bis-chloromethyl-[1,3]dioxan-2-one 

Downstream Products

• 209119-61-9 Benzoic acid (1R,3S)-1-chloromethyl-3-hydroxy-5-methylene-non-8-enyl ester 
• 209119-62-0 Benzoic acid (1R,3R)-1-chloromethyl-3-hydroxy-7-methoxycarbonyl-5-oxo-heptyl ester 
• 209119-59-5 Benzoic acid (1R,3R)-4-chloro-1-chloromethyl-3-hydroxy-butyl ester 
• 209119-60-8 Benzoic acid (R)-1-chloromethyl-2-(R)-oxiranyl-ethyl ester 
• 1061330-08-2 (R)-4-(4-methoxyphenylmethoxy)cyclopent-2-enone 
• 59995-48-1 (R)-4-acetoxycyclopent-2-en-1-one 
• 1426140-06-8 (3Z,5E)-1-[(4R,6S)-6-allyl-2,2-dimethyl-1,3-dioxan-4-yl]-4-hydroxy-6-phenylhexa-3,5-dien-2-one 
• 1426140-05-7 (E)-1-[(4R,6S)-6-allyl-2,2-dimethyl-1,3-dioxan-4-yl]-4-hydroxy-6-phenylhex-5-en-2-one 
• 1426140-00-2 (S)-6-{[(R)-4-oxo-6-[(E)-styryl]-3,4-dihydro-2H-pyran-2-yl]methyl}-5,6-dihydro-2H-pyran-2-one 
• 1426140-07-9 (R)-2-[(S)-2-hydroxypent-4-en-1-yl]-6-[(E)-styryl]-2H-pyran-4(3H)-one 
• 135943-83-8 (2S,4S)-1,5-diphenyl-2,4-pentanediol 
• 135943-79-2 (3S,5R)-5,6-epoxy-1-phenyl-3-hexanol 

Relevant articles and documents

Synthesis of a key building block for a butyrolactone → 1,3-diol approach to the polyol part of roflamycoin

For preparing tris(γ-lactone) 3 the mono(γ-lactone) 6 was synthesized from the dichlorodiol 12 (99.8% ee). Bisepoxide 9 - derived from dichlorodiol 12 (99.8% ee) - was ring-opened with the Gilman cuprate from 2-lithio-1,5-hexadiene and Cul giving almost exclusively the monoepoxide 21; in five more steps, γ-lactone 30 with the same stereotriad as the target molecule 6 but a different protecting group was obtained. Monoepoxide 33 - also derived from dichlorodiol 12 - was ring-opened with the same Gilman cuprate affording compound 35. It was transformed into the correctly protected γ-lactone 6 in seven steps, key reactions being the ozonolysis 35 → 36 and the diastereoselective reduction 36 → anti-37.