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Usage

Uses

Used in Pharmaceutical Industry:
(2S,3S)-(-)-3-PROPYLOXIRANEMETHANOL, 96 is used as a chiral building block for the synthesis of pharmaceuticals. Its ability to form stable and selective complexes with a variety of metal catalysts makes it a valuable component in the development of enantioselective reactions and the production of chiral drugs.
Used in Agrochemical Industry:
In the agrochemical industry, (2S,3S)-(-)-3-PROPYLOXIRANEMETHANOL, 96 is utilized as a chiral building block for the synthesis of agrochemicals. Its enantioselective properties allow for the creation of more effective and targeted pesticides and other agricultural chemicals.
Used in Flavoring Agents Industry:
(2S,3S)-(-)-3-PROPYLOXIRANEMETHANOL, 96 is also used as a chiral building block in the production of flavoring agents. Its ability to create enantioselective compounds contributes to the development of unique and specific flavors in the food and beverage industry.
Safety Precautions:
It is important to handle and store (2S,3S)-(-)-3-PROPYLOXIRANEMETHANOL, 96 in a well-ventilated area, away from heat, sparks, and open flames, as it is flammable. Additionally, it may cause irritation to the respiratory system, skin, and eyes upon exposure, so proper protective measures should be taken when working with (2S,3S)-(-)-3-PROPYLOXIRANEMETHANOL, 96.

InChI:InChI=1/C6H12O2/c1-2-3-5-6(4-7)8-5/h5-7H,2-4H2,1H3/t5-,6-/m0/s1

Upstream product

• 928-95-0 (E)-2-Hexen-1-ol 
• 113525-02-3 (2S,3R)-3-Chlorohexane-1,2-diol 
• 113566-32-8 (2S,3R)-3-Chlorotridecane-1,2-diol 
• 115116-02-4 (2R,3S)-3-propyloxirane-2-carbaldehyde 
• 6728-26-3 (E)-2-Hexenal 
• 113524-86-0 ethyl 3-chloro-2-oxotridecanoate 
• 113566-29-3 Ethyl (2S,3R)-3-chloro-2-hydroxytridecanoate 
• 28942-46-3 Ethyl 3-chloro-2-oxohexanoate 
• 113524-87-1 Ethyl (2S,3R)-3-chloro-2-hydroxyhexanoate 
• 2305-21-7 2-hexen-1-ol 
• 89395-00-6 2,3-epoxyhexan-1-ol 
• 62-53-3 aniline 
• 546-68-9 titanium(IV) isopropylate 
• 505-57-7 2-hexenal 

Downstream Products

• 138611-21-9 (2R,3R)-3-Hexylamino-hexane-1,2-diol 
• 138611-22-0 (2R,3S)-2-Hexylamino-hexane-1,3-diol 
• 135821-40-8 (2R,3R)-3-Cyano-1,2-hexanediol 
• 135821-47-5 (S)-2-((R)-2-Hydroxy-1-trimethylsilanyloxy-ethyl)-pentanenitrile 
• 128224-85-1 (S)-2-Hydroxymethyl-3-trimethylsilanyloxy-hexanenitrile 
• 138611-29-7 (2R,3R)-3-(4-Methoxy-benzylamino)-hexane-1,2-diol 
• 138611-30-0 (2R,3S)-2-(4-Methoxy-benzylamino)-hexane-1,3-diol 
• 110193-11-8 (2S,3R)-3-stearoylhexane-1,2,3-triol 
• 110193-12-9 (2S,3R)-1-stearoylhexane-1,2,3-triol 
• 138611-27-5 (2R,3R)-3-Benzylamino-hexane-1,2-diol 
• 879558-82-4 (2R,3R)-3-azidohexane-1,2-diol 
• 159700-68-2 (2S,3S)-3-Methyl-hexane-1,2-diol 
• 138611-25-3 (2R,3R)-3-(α-phenylbenzylamino)-1,2-hexanediol 
• 107076-91-5 (2S,3S)-(3-propyloxiran-2-yl)methanol O-benzyl ether 

Relevant academic research and scientific papers

Efficient polymer-supported Sharpless alkene epoxidation catalyst

Linear poly(tartrate ester) ligands provide high chemical yields and enantiomeric excesses in the epoxidation of trans-hex-2-en-1-ol using Ti(OPri)4-tert-butyl hydroperoxide.

Efficient soluble polymer-supported Sharpless alkene epoxidation catalysts

High chemical yields and good enantiomeric excesses are obtained by using soluble polymer-supported tartrate ester in the epoxidation of trans-hex-2-en-1-ol using Ti(OPri)4/tert-butyl hydroperoxide.

Br?nsted acid promoted intramolecular cyclization of O-alkynyl benzoic acids: Concise total synthesis of exserolide F

Herein we report the stereoselective total synthesis of Exserolide F. The key step involves triflic acid catalyzed highly regioselective intramolecular cyclization of an O-alkynyl benzoic acid derivative to accomplish the core isocoumarin skeleton of the natural product via 6-endo-dig mode of cyclization. The other important steps are: Sharpless asymmetric epoxidation, Barbier propargylation, Sonogashira coupling en route to access the O-alkynyl benzoic acid derivative.

New chiral amino alcohol ligands for catalytic enantioselective addition of diethylzincs to aldehydes

A study aimed at the synthesis and structure optimization of new, efficient, optically active β-amino alcohol ligands with a structure suitable for immobilization on magnetite nanoparticles has been carried out. The optimized homogeneous amino alcohol catalysts 13a and 13b, the chirality of which arises from the Sharpless epoxidation of suitable allyl alcohols, were tested by employing the well-established enantioselective amino alcohol-promoted addition of diethylzinc to benzaldehyde, giving the corresponding benzyl alcohol with nearly quantitative yield and ee = 95%. Then, their broad applicability as chiral catalysts was evaluated by carrying out the same reaction on a family of aldehydes, including variously substituted aromatic ones as well as an aliphatic analogue. The results have confirmed the validity of the fine-tuning process performed on ligands 13a and 13b. In fact, both exhibited excellent catalytic activity as demonstrated by the chemical yields and ee obtained from all the tested aldehydes, almost independent of the position and type of substitution in the aromatic ring.

Asymmetric epoxidation of α,β-unsaturated aldehydes catalyzed by a spiro-pyrrolidine-derived organocatalyst

The asymmetric epoxidation of α,β-unsaturated aldehydes, catalyzed by a spiro-pyrrolidine (SPD)-derived organocatalyst, has been accomplished with good diastereoselectivities (up to dr >20:1) and with high to excellent enantioselectivities (up to 99% ee).

Kinetic resolution of epoxy alcohols with the Sharpless Ti-isopropoxide/tartaric ester complex

When investigating the Sharpless epoxidation of enol-protected 4-hydroxy-1,2-cyclopentanediones, the ability of the asymmetric Ti(OiPr)4/tartaric ester complex to discriminate between enantiomeric epoxides formed in situ was discovered, leading to the epoxide opening reaction of only one enantiomer. This observation was used in the kinetic resolution of racemic substituted 2,3-epoxy-4-hydroxy-cyclopentanol, to afford enantiomerically enriched epoxyalcohols in good yields and with ees up to 96%.

Asymmetric epoxidation of allylic alcohols catalyzed by vanadium-binaphthylbishydroxamic acid complex

A vanadium-binaphthylbishydroxamic acid (BBHA) complex-catalyzed asymmetric epoxidation of allylic alcohols is described. The optically active binaphthyl-based ligands BBHA 2a and 2b were synthesized from (S)-1,1'-binaphthyl-2,2'dicarboxylic acid and N-substituted-O-trimethylsilyl (TMS)-protected hydroxylamines via a one-pot, three-step procedure. The epoxidations of 2,3,3-trisubstituted allylic alcohols using the vanadium complex of 2a were easily performed in toluene with a TBHP water solution to afford (2R)-epoxy alcohols in good to excellent enantioselectivities.

Eu(OTf)3-Catalyzed highly regioselective nucleophilic ring opening of 2,3-epoxy alcohols: An efficient entry to 3-substituted 1,2-diol derivatives

In our study of the total synthesis of (+)-irciniastatin A, we found a need to develop a method that enables a C3-selective nucleophilic ring opening of 2,3-epoxy alcohol by MeOH, by which we found that the use of combined catalytic amounts of Eu(OTf)3 and 2,6-di-tert-butyl-4-methylpyridine (DTBMP) enables the intended transformation to obtain 3-methoxy-1,2-diol efficiently. Promising features of a protocol that effects a highly regioselective nucleophilic ring opening of 2,3- and 3,4-epoxy alcohols using various nucleophiles including alcohols, thiols, and unprotected amines are described.

Tungsten-catalyzed asymmetric epoxidation of allylic and homoallylic alcohols with hydrogen peroxide

A simple, efficient, and environmentally friendly asymmetric epoxidation of primary, secondary, tertiary allylic, and homoallylic alcohols has been accomplished. This process was promoted by a tungsten-bishydroxamic acid complex at room temperature with the use of aqueous 30% H2O2 as oxidant, yielding the products in 84-98% ee.

Tungsten-catalyzed regio- and enantioselective aminolysis of trans-2,3-epoxy alcohols: An entry to virtually enantiopure amino alcohols

The first catalytic enantioselective aminolysis of trans-2,3-epoxy alcohols has been accomplished. This stereo-specific ring-opening process was efficiently promoted by a tungsten/bis(hydroxamic acid) catalytic system, furnishing various anti-3-amino-1,2-diols with excellent regiocontrol and high enantioselectivities (up to 95% ee). Moreover, virtually enantiopure 3-amino-1,2-diols could be obtained by the sequential combination of two reactions that both involve the use of a chiral catalyst.