108340-61-0

Basic information

• Product Name: (R)-(+)-1,2-PENTANEDIOL
• Synonyms: (R)-(+)-1,2-PENTANEDIOL;(2R)-1,2-Pentanediol;(2R)-Pentane-1,2-diol;(R)-Pentane-1,2-diol
• CAS NO: 108340-61-0
• Molecular Formula: C₅H₁₂O₂
• Molecular Weight: 104.14758
• Mol File: 108340-61-0.mol
• Article Data: 17

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (R)-(+)-1,2-PENTANEDIOL(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(+)-1,2-PENTANEDIOL(108340-61-0)
• EPA Substance Registry System: (R)-(+)-1,2-PENTANEDIOL(108340-61-0)

Safety Data

• Hazardous Substances Data: 108340-61-0(Hazardous Substances Data)

Usage

General Description

(R)-(+)-1,2-Pentanediol is a chiral organic compound with the molecular formula C5H12O2. It exists as a colorless, viscous liquid and is commonly used as a solvent, a humectant in cosmetic formulations, and as a precursor in the synthesis of various chemicals. Due to its chiral nature, (R)-(+)-1,2-Pentanediol finds applications in asymmetric synthesis and as a chiral resolving agent. It is also used in the production of plasticizers, and as a component in the manufacturing of pharmaceuticals and agricultural products. Additionally, (R)-(+)-1,2-Pentanediol has antimicrobial properties, making it suitable for use in personal care products and disinfectants.

Upstream product

• 139164-92-4 (3R)-1-hexen-3-ol 
• 64502-89-2 1-hydroxypentan-2-one 
• 5343-92-0 1,2-pentanediol 
• 81947-72-0 1,2-diacetoxypentane 
• 1003-14-1 2-pentyloxirane 
• 6600-40-4 L-Norvaline 
• 109-67-1 1-penten 
• 41014-93-1 2-(S)-hydroxyvaleric acid 
• 24809-83-4 (2R)-2-hydroxypentanoic acid 
• 2013-12-9 D-norvaline 
• 100-52-7 benzaldehyde 
• 19265-24-8 1-chloropentane-2-one 
• 887502-32-1 (2R,3R)-3-benzyloxy-hexane-1,2-diol 
• 117935-05-4 (R)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)but-2-yn-1-ol 

Downstream Products

• 529510-44-9 (R)-(+)-2-hydroxypentyl tosylate 
• 63095-51-2 (+)-(R)-4-propyl-4,5-dihydrofuran-2(3H)-one 

Relevant articles and documents

A novel generation of optically active 1,2-diols from the racemates by using halohydrin dehydro-dehalogenase

A novel enzyme dehalogenating halohydrins, designated as halohydrin dehydo-dehalogenase (HDDase), was purified from Alcaligenes sp. DS-S-7G. The enzyme catalyzed oxidative dehalogenation of (R)-3-chloro-1,2-propanediol [monochlorohydrin (MCH)] to acetic acid and formaldehyde via hydroxyacetone stereoselectively by the addition of artificial electron acceptors. The dehalogenating activity was much higher in the presence of 2,6- dichlorophenolindophenol (DCIP) and phenazine methosulfate (PMS). The resulting stereoselective dehydro-dehalogenation was applicable to preparation of various optically active halohydrins and 1,2-diols so that the respective residual isomers had excellent enantiomeric excesses (ee) (60-99% ee).

The stereoselective conversion of 2-alkenyl alcohols to (R)- or (S)- alkane-1, 2-diols using D-glucose as a chiral auxiliary

The stereoselective addition of the 2-hydroxyl group of glucose to the mercurated vinyl group of 2-alkenyl glycosides followed by hydride reduction and removal of the saccharide fragment was used to prepare enantiomerically pure 1,2-dihydroxy alkanes. Diols of (R) or (S) configuration can be synthesized from (α)-glycosides or the (β) form respectively. Demercuration with chloride ion led to the insertion of a halo group adjacent to the new chiral center thus allowing for the possibility of further functionalization.

Total Synthesis of the Antitumor Depsipeptide FE399 and Its S-Benzyl Derivative: A Macrolactamization Approach

An efficient and practical method for the synthesis of (9R,14R,17R)-FE399, a novel antitumor bicyclic depsipeptide, was developed. A 2-methyl-6-nitrobenzoic anhydride (MNBA)-mediated dehydration condensation reaction was effectively employed for the formation of the 16-membered macrocyclic depsipeptide moiety of FE399. FE399 was found to exist as an inseparable equilibrium mixture of conformational isomers; the mixture was quantitatively transformed into the corresponding S-benzyl product and isolated as a single isomer. Thus, we could confirm that the molecular structure of FE399 obtained by this method is identical to that of the natural product.

Efficient enantioselective synthesis of optically active diols by asymmetric hydrogenation with modular chiral metal catalysts

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Catalytic asymmetric allylation of aldehydes using the chiral (salen)chromium(III) complexes

The enantioselective addition of allylstannanes to glyoxylates and glyoxals, as well as simple aromatic and aliphatic aldehydes, catalyzed by chiral (salen)Cr(III) complexes, has been studied. The reaction proceeded smoothly for the reactive 2-oxoaldehydes and allyltributyltin in the presence of small amounts (1-2 mol %) of (salen)Cr(III)BF4 (1b) under mild, undemanding conditions. However, in the case of other simple aldehydes, the use of high-pressure conditions is required to obtain good yields. Classic chromium catalyst 1b, easily prepared from the commercially available chloride complex 1a, affords homoallylic alcohols usually in good yield and with enantiomeric purity of 50-79% ee. The stereochemical results are rationalized on the basis of the proposed model.