22422-34-0

Usage

Uses

Used in Pharmaceutical Applications:
(1R,2R,3S,5R)-(-)-2,3-Pinanediol is used as a therapeutic agent for its ability to induce differentiation in certain types of cancer cells, such as S91 melanoma and PC12 pheochromocytoma cells. This property makes it a promising candidate for cancer treatment and research.
Used in Cosmetic Applications:
(1R,2R,3S,5R)-(-)-2,3-Pinanediol is used as an ingredient in the cosmetic industry for its potential in sunless tanning. This application takes advantage of the compound's ability to induce cell differentiation, which could lead to a tanning effect without the need for exposure to sunlight or its associated risks.
Used in Flavor and Fragrance Industry:
(1R,2R,3S,5R)-(-)-2,3-Pinanediol, being a microbial oxidation product of (-)-β-pinene, a flavor and fragrance monoterpene, can be used as a component in the creation of various fragrances and flavors, leveraging its unique chemical properties to enhance or create new sensory experiences.

InChI:InChI=1/C10H18O2/c1-9(2)6-4-7(9)10(3,12)8(11)5-6/h6-8,11-12H,4-5H2,1-3H3/t6-,7-,8-,10+/m0/s1

Upstream product

• 1845-25-6 (-)-(2R,3R,5R)-2-hydroxy-3-pinanone 
• 80-56-8 rac-α-pinene 
• 7785-70-8 (+)-α-pinene 
• 7785-26-4 (-)-α-pinene 
• 80-56-8 Pinene 
• 60-29-7 diethyl ether 
• 22466-70-2 (1R,2S,5R)-6,6-dimethylspiro[bicycle[3.1.1]heptane-2,2’-oxiran]-3-one 

Downstream Products

• 612835-98-0 (1R,2R,6S,8R)-4-(Dimethyl-phenyl-silanyl)-2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.0^2,6]decane 
• 132488-71-2 B(OC(CH₃)CH(C(CH₃)2)CH₂CHCH₂CHO)(CHCH₂) 
• 76155-63-0 (-)-pinandiol (S)-1-phenylethane-1-boronate 
• 7205-03-0 phenylbismuth(III) diacetate 
• 603-33-8 triphenylbismuthane 
• 1414867-92-7 4-(3-(2-hydroxyphenyl)-5-(2-((4-(3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborol-2-yl)benzyl)oxy)phenyl)-1H-1,2,4-triazol-1-yl)benzoic acid 
• 1845-25-6 (-)-(2R,3R,5R)-2-hydroxy-3-pinanone 
• 90473-01-1 (1R,2R,5R)-ethyl-((2-hydroxypinan-3-ylene)amino)acetate 

Relevant academic research and scientific papers

Enantioselective Total Synthesis of the Putative Biosynthetic Intermediate Ambruticin J

The family of anti-fungal natural products known as the ambruticins are structurally distinguished by a pair of pyran rings adorning a divinylcyclopropane core. Previous characterization of their biosynthesis, including the expression of a genetically modified producing organism, revealed that the polyketide synthase pathway proceeds via a diol intermediate, known as ambruticin J. Herein, we report the first enantioselective total synthesis of the putative PKS product, ambruticin J, according to a triply convergent synthetic route featuring a Suzuki-Miyaura cross-coupling and a Julia-Kocienski olefination for fragment assembly. This synthesis takes advantage of synthetic methodology previously developed by our laboratory for the stereoselective generation of the trisubstituted cyclopropyl linchpin.

Synthesis of novel chiral bisphosphinites from α-pinene

Chiral bisphosphinites 5 were obtained by dihydroxylation of (-)-α-pinene (1) followed by deprotonation and treatment with chlorophosphines 3. Unlike their corresponding borane adducts 4, compounds 5 turned out to be very sensitive.

Boric acid compounds, and preparation method and use thereof

The invention relates to the fields of pharmaceutical chemistry and medicine therapeutics, concretely relates to a new boric acid compounds, and a preparation method and a use thereof, and especially relates to new substituted five-membered heterocyclic boric acid and substituted benzo five-membered boric acid compounds, and a preparation method thereof. A result of bioactive screening test of the substituted five-membered heterocyclic boric acid and substituted benzo five-membered boric acid compounds having a structure represented by a formula shown in the description shows that the compounds have a proteasome inhibition effect, and can be further used for preparing medicines for treating proteasome correlated diseases.

NOVEL SYNTHESIS INTERMEDIATES FOR OBTAINING DERIVATIVES OF SPHINGOSINES, CERAMIDES AND SPHINGOMYELINS WITH GOOD YIELDS

The subject matter of the present invention is the novel molecules of formulae E, E′ and F. These molecules prove to be synthesis intermediates that are very advantageous for the manufacture of derivatives of sphingosine or of ceramides functionalized in position 1, with good yields, in which R1 and R2 are fatty chains, R3 is an alkyl group and R4 is a protective group for alcohol functions. Another subject of the invention is the use of the intermediates of type F for converting same into intermediates of type G, by means of reduction in the presence of lithium borohydride. The G molecules are precursors that are known to make it possible to obtain sphingolipids or sphingomyelin.

Synthetic method of chiral vicinal diol and product thereof

The invention provides a synthetic method of chiral vicinal diol, which comprises the following steps: (1) adding alkene used as a precursor of the chiral vicinal diol and dichloromethane into a reaction device, adding alkali, and then at a temperature of minus 50 DEG C to minus 15 DEG C, adding a phase-transfer catalyst and then adding potassium permanganate or sodium permanganate in batches to perform a reaction so as to obtain an intermediate a; (2) adding the intermediate a into the reaction device, adding ethyl ether and petroleum ether with stirring, then adding boric acid in batches, and dropwise adding aqueous solution of potassium hydroxide to perform a reaction so as to obtain an intermediate b; (3) adding the intermediate b into the reaction device, adding ethyl ether and water, and then under the ice bath cooling condition, dropwise adding hydrofluoric acid, and stirring overnight at a low temperature to obtain the chiral vicinal diol. According to the synthetic method provided by the invention, the potassium permanganate or the sodium permanganate which is cheap, has low toxicity and pollutes the environment a little is used as a reaction reagent, and industrial synthetic production of a chiral vicinal diol compound is achieved.

A Modular Approach to the Asymmetric Synthesis of Cytisine

The asymmetric synthesis of (+)-and (-)-cytisine starts with Matteson homologations for the construction of a chiral C3-building block. Conversion of the C3-building block into a dihydropyridone is achieved by straightforward functional group interconversions and ring closing metathesis. After bromination, this central building block was diastereospecifically converted into cytisine in five steps.

Preparation and application of 2-(arylmethoxy)isopinocampheols for the asymmetric aldol reaction of 3,3,3-trifluoropropionates

The preparation of 2-(arylmethoxy)isopinocampheols from pinanediol via the DIABL-H reduction of the corresponding aryl aldehyde acetals has been described. A systematic examination of the asymmetric aldol reaction of 3,3,3-trifluoropropionates led to the double diastereoselective aldol reaction of 2-(arylmethoxy)isopinocampheyl 3,3,3-trifluoropropionates providing anti-α-trifluoromethyl-β-hydroxy esters in 63-85% yields, ≥99% anti-selectivity and 80-96% de for the anti-isomer.

Design, synthesis, biological evaluation, and Structure-Activity Relationship (SAR) discussion of dipeptidyl boronate proteasome inhibitors, Part I: Comprehensive understanding of the SAR of α-amino acid boronates

New series of dipeptidyl boronate inhibitors of 20S proteasome were designed and synthesized. The comprehensive understanding of the SAR was obtained by utilizing the variation of four substituents. From the screened compounds in enzyme, novel inhibitors 49 and 50 were identified to be highly potent druglike candidates with IC50 values of 1.2 and 1.6 nM, respectively, which showed better activities than the drug bortezomib on the market. Two hematologic human tumor cell lines, HL-60 and U266, were significantly sensitive to both candidates and showed nearly the same potency as the standard bortezomib with IC50 values less than 10 nM. But as for most of the eight human solid tumor cell lines, both candidates were more potent than the standard with the IC50 value range of 9.8-70 nM. The activity evaluation of the stereoisomers showed that changing R-isomers to S-isomers greatly reduced the potency and even induced inactivity.

Accelerating ligands for osmium tetraoxide catalyzed racemic dihydroxylation of α-pinene

Osmium tetraoxide catalyzed racemic cis-dihydroxylation of α-pinene usinf N-oxide as cooxidant and hexamethylenetetraamine as accelerating ligand in tert-butyl alcohol gives excellent yield of α-pinanediol.

Monoterpenediol insect repellents

An insect repellent comprising as an active ingredient a monoterpenediol compound having the formula, STR1 wherein R1, R2 and R3 have either one of the following definitions: (i) all of R1, R2 and R3 are hydrogen, (ii) R1 is hydrogen and R2 and R3, taken together, form a carbon-carbon single bond, or (iii) R2 is hydrogen, R1 and R3, taken together, form a carbon-carbon single bond, and the hydroxyl bonded to the carbon atom marked with an asterisk takes an α-configuration.