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Usage

Uses

Used in Cosmetics and Skincare Industry:
(R)-1,2-TETRADECANEDIOL is used as an emollient and moisturizer for its ability to hydrate and soften the skin. It is particularly favored in the formulation of lip balms, creams, and other skincare products to provide a smooth and moisturizing effect.
Used in Personal Care Industry:
In the personal care sector, (R)-1,2-TETRADECANEDIOL serves as an ingredient in products that require emollience and moisturization, enhancing the skin's softness and suppleness.
Used in Chemical Formulations:
(R)-1,2-TETRADECANEDIOL is also utilized as a component in surfactants and other chemical formulations, where its solubility and emollient properties are beneficial for the development of effective and high-quality products.

Upstream product

• 56009-40-6 (R)-methyl 2-hydroxytetradecanoate 
• 3234-28-4 1,2-epoxytetradecane 
• 2507-55-3 (R)-α-hydroxymyristic acid 
• 1120-36-1 1-tetradecene 
• 75-96-7 tribromoacetic acid 
• 3234-28-4 (R)-(+)-1,2-epoxytetradecane 

Downstream Products

• 636596-53-7 (4S)-4-[(3'R,4'R)-4'-(tert-butyldimethylsilyloxy)-3'-hydroxyoctadecanyl]-2-phenyl-1,3-dioxolane 
• 929915-17-3 (4S)-4-[(3'R,4'R)-4'-(tert-butyldimethylsilyloxy)-3'-hydroxy-1'-hexadecynyl]-2-phenyl-1,3-dioxolane 
• 1053255-07-4 Toluene-4-sulfonic acid (1R,2R)-2-(tert-butyl-dimethyl-silanyloxy)-1-((S)-3,4-dihydroxy-butyl)-tetradecyl ester 
• 636596-54-8 (4S)-4-[(3'R,4'R)-4'-(tert-butyldimethylsilyloxy)-3'-(p-toluenesulfonyloxy)octadecanyl]-2-phenyl-1,3-dioxolane 
• 460745-02-2 (2S,5R,6R)-6-(tert-butyldimethylsilyloxy)-2,5-dihydroxyoctadecanyl 2',4',6'-triisopropylbenzenesulfonate 
• 212205-70-4 ((1R,2R)-2-Methoxymethoxy-1-vinyl-tetradecyloxy)-acetic acid (2S,4S)-2-(4-bromo-benzyloxymethyl)-3,4-dihydro-2H-pyran-4-yl ester 

Relevant academic research and scientific papers

Site-Selective Mono-Oxidation of 1,2-Bis(boronates)

Site-selective oxidation of vicinal bis(boronates) is accomplished through the use of trimethylamine N-oxide in 1-butanol solvent. The reaction occurs with good efficiency and selectivity across a range of substrates, providing 2-hydro-1-boronic esters which are shown to be versatile intermediates in the synthesis of chiral building blocks.

Carbohydrate/DBU Cocatalyzed Alkene Diboration: Mechanistic Insight Provides Enhanced Catalytic Efficiency and Substrate Scope

A mechanistic investigation of the carbohydrate/DBU cocatalyzed enantioselective diboration of alkenes is presented. These studies provide an understanding of the origin of stereoselectivity and also reveal a strategy for enhancing reactivity and broadening the substrate scope.

Carbohydrate-Catalyzed Enantioselective Alkene Diboration: Enhanced Reactivity of 1,2-Bonded Diboron Complexes

Catalytic enantioselective diboration of alkenes is accomplished with readily available carbohydrate-derived catalysts. Mechanistic experiments suggest the intermediacy of 1,2-bonded diboronates.

One-pot conversions of olefins to cyclic carbonates and secondary allylic and homoallylic amines to cyclic carbamates

Sequential treatment of a 1,2-disubstituted olefin with m-CPBA, Br 3CCO2H, and DBU results in the one-pot, stereospecific conversion of the olefin to the corresponding disubstituted cyclic carbonate (1,3-dioxolan-2-one). The reaction proceeds via an initial epoxidation followed by SN2-type epoxide ring opening by Br3CCO2H and subsequent base-promoted carbonate formation upon elimination of bromoform. When a solution of a secondary allylic or homoallylic amine and Br 3CCO2H is sequentially treated with m-CPBA then DBU, the product of the reaction is a cyclic carbamate (1,3-oxazolidin-2-one or 1,3-oxazinan-2-one).

Methanesulfonamide: A cosolvent and a general acid catalyst in sharpless asymmetric dihydroxylations

To obtain information about the effect that methanesulfonamide has in the hydrolysis step in Sharpless asymmetric dihydroxylation, a series of aliphatic and conjugated aromatic olefins were dihydroxylated with and without methanesulfonamide. The hypothesis in this study was that methanesulfonamide is a cosolvent that aids in the transfer of the hydroxide ions from the water phase to the organic phase. A plot of t90% versus the computational partition coefficient clog P of the intermediate osmate ester of nonterminal aliphatic olefins revealed that the polarity of the intermediate osmate ester has a significant effect on the reaction time and methanesulfonamide effect. The more polar the intermediate osmate ester, the faster is the reaction without methanesulfonamide and the smaller the accelerating methanesulfonamide effect. Methanesulfonamide had no accelerating effect in the asymmetric dihydroxylation of short chain terminal aliphatic olefins as a result of easier accessibility of terminal osmate ester groups to the water phase. A cosolvent hypothesis was found not to be valid in asymmetric dihydroxylations of conjugated aromatic olefins. In the reaction conditions used in Sharpless asymmetric dihydroxylation, weakly acidic methanesulfonamide was found to be a general acid catalyst that protonates the intermediate osmate esters of conjugated aromatic olefins in the hydrolysis step.

De novo sythesis of a D-galacturonic acid thioglycoside as key to the total synthesis of a glycosphingolipid from

A concise synthesis of a differentially protected D-galacturonic acid (D-GalA) thioglycoside and the construction of a potent immunomodulating glycosphingolipid are described. The key steps of the synthesis are an Evans aldol reaction between a C4 aldehyde and a PMB-protected glycolyloxazolidinone as well as a tandem-PMB-deprotection/cyclization to thioglycosides. The key glycosylation step is optimized by varying the anomeric leaving group, the activating agent, and the solvent system.

Highly selective hydrolytic kinetic resolution of terminal epoxides catalyzed by chiral (salen)CoIII complexes. Practical synthesis of enantioenriched terminal epoxides and 1,2-diols

The hydrolytic kinetic resolution (HKR) of terminal epoxides catalyzed by chiral (salen)CoIII complex 1·OAc affords both recovered unreacted epoxide and 1,2-diol product in highly enantioenriched form. As such, the HKR provides general access to useful, highly enantioenriched chiral building blocks that are otherwise difficult to access, from inexpensive racemic materials. The reaction has several appealing features from a practical standpoint, including the use of H2O as a reactant and low loadings (0.2-2.0 mol %) of a recyclable, commercially available catalyst. In addition, the HKR displays extraordinary scope, as a wide assortment of sterically and electronically varied epoxides can be resolved to ≥ 99% ee. The corresponding 1,2-diols were produced in good-to-high enantiomeric excess using 0.45 equiv of H2O. Useful and general protocols are provided for the isolation of highly enantioenriched epoxides and diols, as well as for catalyst recovery and recycling. Selectivity factors (krel) were determined for the HKR reactions by measuring the product ee at ca. 20% conversion. In nearly all cases, krel values for the HKR exceed 50, and in several cases are well in excess of 200.