68394-39-8

Basic information

• Product Name: (2S,3S)-(-)-bis(dibenzyloxymethyl)-2,2-dimethyl-1,3-dioxolane
• Synonyms: (2S,3S)-(-)-bis(dibenzyloxymethyl)-2,2-dimethyl-1,3-dioxolane
• CAS NO: 68394-39-8
• Molecular Weight: 342.435
• Mol File: 68394-39-8.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: (2S,3S)-(-)-bis(dibenzyloxymethyl)-2,2-dimethyl-1,3-dioxolane(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3S)-(-)-bis(dibenzyloxymethyl)-2,2-dimethyl-1,3-dioxolane(68394-39-8)
• EPA Substance Registry System: (2S,3S)-(-)-bis(dibenzyloxymethyl)-2,2-dimethyl-1,3-dioxolane(68394-39-8)

Safety Data

• Hazardous Substances Data: 68394-39-8(Hazardous Substances Data)

Upstream product

• 59779-75-8 diethyl (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate 
• 37031-29-1 (-)-dimethy-2,3-O-isopropylidene-L-tartrate 
• 50622-09-8 2,3-O-isopropylidene-L-threitol 
• 100-44-7 benzyl chloride 
• 100-39-0 benzyl bromide 

Downstream Products

• 88454-98-2 (7S,8S)-7,8-bis((benzyloxy)methyl)-1,14-diiodo-3,6,9,12-tetraoxatetradecane 
• 88454-97-1 (7S,8S)-7,8-bis((benzyloxy)methyl)-1,14-dichloro-3,6,9,12-tetraoxatetradecane 
• 68394-43-4 (2S)-2r,3t-bis-benzyloxymethyl-1,4,10,13-tetraoxa-7,16-diaza-cyclooctadecane-6,17-dione 
• 68394-44-5 (2S)-trans-2,3-bis-benzyloxymethyl-1,4,10,13-tetraoxa-7,16-diaza-cyclooctadecane 
• 68394-40-1 ((1S,2S)-1,2-bis-benzyloxymethyl-ethane-1,2-diyldioxy)-bis-acetic acid 
• 68394-41-2 2,3-di-O-(2-hydroxyethyl)-1,4-di-O-benzyl-L-threitol 
• 126277-52-9 (2S,3S)-(-)-2,3-bis(benzyloxymethyl)-1,4,8,11-tetraoxacyclotetradecane 
• 121466-91-9 (R,R)-1,2-Bis<(benzyloxy)methyl>-15-krone-5 
• 17137-55-2 (2S,3S)-2,3-di(methanesulfonyloxy)-1,4-dibenzyloxybutane 
• 133268-20-9 D-2,3-diazido-1,4-dibenzoylbutane 
• 17401-06-8 (2S,3S)-1,4-bis(benzyloxy)-2,3-butanediol 

Relevant articles and documents

Synthesis of l-threitol-based crown ethers and their application as enantioselective phase transfer catalyst in Michael additions

A few new l-threitol-based lariat ethers incorporating a monoaza-15-crown-5 unit were synthesized starting from diethyl l-tartrate. These macrocycles were used as phase transfer catalysts in asymmetric Michael addition reactions under mild conditions to afford the adducts in a few cases in good to excellent enantioselectivities. The addition of 2-nitropropane to trans-chalcone, and the reaction of diethyl acetamidomalonate with β-nitrostyrene resulted in the chiral Michael adducts in good enantioselectivities (90% and 95%, respectively). The substituents of chalcone had a significant impact on the yield and enantioselectivity in the reaction of diethyl acetoxymalonate. The highest enantiomeric excess (ee) values (99% ee) were measured in the case of 4-chloro- and 4-methoxychalcone. The phase transfer catalyzed cyclopropanation reaction of chalcone and benzylidene-malononitriles using diethyl bromomalonate as the nucleophile (MIRC reaction) was also developed. The corresponding chiral cyclopropane diesters were obtained in moderate to good (up to 99%) enantioselectivities in the presence of the threitol-based crown ethers.

Synthesis and conformational and configurational studies of diastereoisomeric O-protected 4-(arylsulfonimidoyl)butane-1,2,3-triols

Chiral sulfoximines have applications as transition-state mimicking enzyme inhibitors, as peptide isosteres and as chiral auxiliaries in synthesis. To access the required O-protected 4-(arylsulfonimidoyl)butane-1,2,3-triols, 4S,5S-di(hydroxymethyl)-2,2-dimethyl-1,3-dioxolane (prepared from diethyl R,R-tartrate) was converted into its monobenzyl ether. Mitsunobu-like coupling with thiophenols gave 4S,5R-4-(benzyloxymethyl)-2,2-dimethyl-5-(arylthiomethyl)-1,3-dioxolanes. Sulfoxidation and S-imination (trifluoroacetamide, iodosobenzene diacetate, rhodium acetate) proceeded without stereoselectivity, giving inseparable diastereomeric mixtures of 4S,5R,S(±)-4-(benzyloxymethyl)-2,2-dimethyl-5-(N-(trifluoroacetyl)arylsulfonimidoylmethyl)-1,3-dioxolanes. Removal of the trifluoroacetyl protection allowed chromatographic separation of the diastereomeric 4S,5R,S(±)-4-(benzyloxymethyl)-2,2-dimethyl-5-(arylsulfonimidoylmethyl)-1,3-dioxolanes. The configurations at sulfur were determined by X-ray crystallography and some analysis of the solution and solid-state conformations was carried out. The resulting O-protected 4-(arylsulfonimidoyl)butane-1,2,3-triols are of use in developing enzyme inhibitors.

Highly selective Silver(I) oxide mediated monoprotection of symmetrical diols

Treatment of symmetrical diol with Ag2O and alkyl halide gave the monoprotected derivative in good to excellent yield.