86940-98-9

Upstream product

• 109240-71-3 tert-Butyl-dimethyl-((R)-2,2,4-trimethyl-[1,3]dioxolan-4-ylmethoxy)-silane 
• 111219-30-8 Phenyl-acetic acid 2,2,4-trimethyl-[1,3]dioxolan-4-ylmethyl ester 
• 69821-01-8 (R)-2,2,4-trimethyl-1,3-dioxolane-4-carboxylic acid ethyl ester 
• 133805-05-7 <(R,S)-2,2,4-trimethyl-1,3-dioxolan-4-yl>methyl butyrate 
• 365513-17-3 methyl 2,2,4-trimethyl-1,3-dioxolane-4-carboxylate 
• 149525-47-3 <(R)-(2,2,4-trimethyl-1,3-dioxolan-4-yl)>methyl acetate 
• 86884-87-9 (4RS)-4-hydroxymethyl-2,2,4-trimethyl-1,3-dioxolane 
• 86884-93-7 (S)-2,2,4-trimethyl-4-<(phenylsulfinyl)methyl>-1,3-dioxolane 
• 191479-55-7 (S)-2,2,4-Trimethyl-4-phenylethynyl-[1,3]dioxolane 
• 109240-74-6 4-benzyloxymethyl-2,2,4-trimethyl-1,3-dioxolane 
• 86940-99-0 (1S,4R)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (R)-2,2,4-trimethyl-[1,3]dioxolan-4-ylmethyl ester 
• 127062-05-9 (R)-2,2,4-Trimethyl-[1,3]dioxolane-4-carboxylic acid butyl ester 
• 86884-92-6 (R)-(-)-2,2,4-trimethyl-4-<(phenylthio)methyl>-1,3-dioxolane 
• 86884-95-9 2,2,4-trimethyl-4--1,3-dioxolane 

Relevant academic research and scientific papers

An alternative approach to (S)- and (R)-2-methylglycidol O-benzyl ether derivatives

This report describes the gram scale synthesis of (S)- and (R)-2,2,4-trimethyl-4-(hydroxymethyl)-1,3-dioxolanes using the Sharpless asymmetric dihydroxylation (AD) of the Weinreb amide of 2-methyl-2-propenoic acid. The 2-methylglycerol acetonides resultan

Chemoenzymatic enantioselective synthesis of 2-substituted glycerol derivatives

2-Substituted glycerol derivatives 4a-g were resolved by acylation with vinyl butyrate in the presence of lipases in organic media. The reverse reaction, the enzymatic hydrolysis of the corresponding butyrates 5a-g, was also highly stereoselective and pro

Facile synthesis of C2-symmetric chiral crown ethers with two reactive hydroxymethyl groups

Two C2-symmetric chiral crown ethers, (2S,12S)-2,12- bis(hydroxymethyl)-2,12-dimethyl-18-crown-6 and (2R,9R)-2,9-bis(hydroxymethyl)- 2,9-dimethyl-18-crown-6 were synthesized from a chiral subunit, [(45)-2,2,4-trirnethyl-1,3-dioxolane-4-yl]methanol, at high enantiomeric purity over several steps. This synthetic method offers the potential to construct a variety of C2-symmetric chiral crown ethers using diverse combinations of building blocks. Georg Thieme Verlag Stuttgart.

Enantioselective synthesis of tertiary alcohols by the desymmetrizing benzoylation of 2-substituted glycerols

(Chemical Equation Presented) Complementary catalysts have been found for the enantioselective desymmetrization of 2-substituted glycerols by monobenzoylation with benzoyl chloride and Et3N to give chiral tertiary alcohols with 80 to 94% ee (se

Chemo-enzymatic enantioconvergent synthesis of C4-building blocks containing a fully substituted chiral carbon center using bacterial epoxide hydrolases

A highly efficient chemo-enzymatic asymmetric synthesis of chiral C4-building blocks containing a fully substituted carbon center is reported. The key transformation consists of a deracemization based on an enantioconvergent asymmetric hydrolys

Enantioselective hydrolysis of functionalized 2,2-disubstituted oxiranes with bacterial epoxide hydrolases

The biohydrolysis of 2,2-disubstituted oxiranes bearing various oxygen functional groups was investigated using the epoxide hydrolase activity of 11 bacterial strains. The results show that the activity and the selectivity strongly depend on the substrate structure and the biocatalyst. Whereas substrates possessing free hydroxyl groups were not transformed, their analogs, protected as ethers, were well accepted. This allowed the convenient modulation of the enantioselectivity by proper choice of the ether group according to size and polarity. It was found that the distance of the ether-oxygen to the stereogenic quaternary carbon center of the oxirane ring had a profound influence on the enantioselectivity, and several oxiranes were resolved with good to excellent selectivities. The enantiomerically enriched epoxides and vicinal diols thus obtained contain a useful 'synthetic handle' in their side chain, which allows their use as building blocks in asymmetric synthesis.

Preparation of optically active tertiary alcohols by enzymatic methods. Application to the synthesis of drugs and natural products

By the catalysis of AK or porcine pancreas lipases, 3-iodo-2-phenyl- 1,2-propanediol, 1-(hydroxy-methyl)-1-phenyloxirane, 2-(iodomethyl)-4- phenyl-3-butyne-1,2-diol, 2-(iodomethyl)-4-(trimethylsilyl)-3-butyne-1,2- diol, and 5,5-dimethyl-2-(iodomethyl)-3-hexyne-1,2-diol were resolved in very high enantioselectivities (E ≤ 153). The obtained enantiomerically pure or optically enriched compounds, containing an iodo atom, an oxirane moiety, or an alkynyl group, are versatile building blocks for the synthesis of chiral azido diols, sulfanyl diols, cyano diols, the side chain of a vitamin D3 metabolite, the ω-chain of a prostaglandin analog, and an aggregation pheromone (1S,5R)-(-)-frontalin. Models based on the consideration of the importance of size, distance, and electron effect are proposed to interpret the observed stereospecificity in the enzymatic reactions. Thus, the lipase- catalyzed reactions of 1,1-disubstituted 1,2-diols occurred efficiently at the primary hydroxyl groups while the enantioselectivity was controlled by the tertiary carbinyl centers.

Facile Chemoenzymatic Preparation of Enantiomerically Pure 2-Methylglycerol Derivatives as Versatile Trifunctional C4-Synthons

Both enantiomers of a series of synthetically valuable 2-methylglycerol derivatives have been prepared with >99percent ee using a chemoenzymatic reaction sequence.The introduction of chirality was achieved by enantioselective esterification of 1,2-O-protected 2-methylglycerol 3 or enantioselective hydrolysis of its butyryl ester 4.The enzymatic reaction proceeded with unusually high selectivity and velocity for a primary alcohol (ester) substrate.

Optically Active Quaternary Carbon Centers from the Photoaddition of Chromium-Alkoxycarbene Complexes and Optically Active Thiazolines

The photolytic reaction of chromium-alkoxycarbene complexes with valine-derived, optically active thiazolines produced optically active β-lactam penam derivatives in fair to good yield and with high diastereoselectivity.In most cases alcoholysis of the β-lactam followed by solvolysis of the thiazolidine ring produced optically active quaternary centers having carbon substituents in four different oxidation states - alkane, alkoxy, aldehyde, and ester.The absolute configuration of the stereogenic center could be inverted by a sequence of redox manipulations of the ester and aldehyde group, making either enantiomer available from the same precursor.