64491-68-5

Usage

Chemical Properties

Colorless to light yellow liqui

InChI:InChI=1/C4H8O2/c1-5-2-4-3-6-4/h4H,2-3H2,1H3/t4-/m1/s1

Upstream product

• 930-37-0 glycidyl methyl ether 
• 57044-25-4 (R)-oxiranemethanol 
• 74-88-4 methyl iodide 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 276860-68-5 (2S)-2-[N-benzyl-N-[(2S)-2-hydroxy-3-methoxypropyl]amino]-1-propanol 
• 473610-19-4 [3-({4-[(2S)-2-Hydroxy-3-methoxypropyl]-1-piperazinyl}carbonyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)-yl][2-methyl-2'-trifluoromethyl-[1,1'-biphenyl]-4-yl]methanone 
• 944952-92-5 (R)-1-methoxy-3-[(3S,4R,5R)-4-(4-methoxyphenyl)-5-[4-(3-methoxypropyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-1-(toluene-4-sulfonyl)piperidin-3-yloxy]propan-2-ol 
• 1323393-99-2 (S)-9-[(3-methoxy-2-hydroxy)propyl]-6-O-benzylguanine 
• 1323394-14-4 (S)-1-[(3-methoxy-2-hydroxy)propyl]-N₄-(p-monomethoxytrityl)cytosine 
• 1414571-12-2 (S)-1-(5-amino-4-methyl-1-phenyl-1H-pyrazol-3-yloxy)-3-methoxypropan-2-ol 
• 1085543-96-9 (2S)-1-amino-3-methoxy-2-propanol 
• 1589599-30-3 (2S)-2-hydroxy-3-methoxy-S-(4-nitrophenyl)propane-1-sulfonamide 
• 1019256-92-8 (R)-1-methoxy-3-[(3S,4R,5R)-4-[4-((S)-3-methoxy-2-methyl-propoxymethyl)-phenyl]-5-[4-(3-methoxy-propyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-1-(toluene-4-sulfonyl)-piperidin-3-yloxy]-propan-2-ol 
• 1006865-85-5 tert-butyl (3S,4R,5R)-3-((R)-2-hydroxy-3-methoxy-propoxy)-4-(4-methoxy-phenyl)-5-[4-(3-methoxy-propyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl-methoxy]piperidine-1-carboxylate 
• 912346-26-0 (R)-1-[(3S,4R,5R)-4-(4-cyclopropylmethoxymethylphenyl)-5-[4-(3-methoxypropyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-1-(toluene-4-sulphonyl)piperidin-3-yloxy]-3-methoxypropan-2-ol 

Relevant academic research and scientific papers

Enantioselective Resolution Copolymerization of Racemic Epoxides and Anhydrides: Efficient Approach for Stereoregular Polyesters and Chiral Epoxides

Herein we report an efficient strategy for preparing isotactic polyesters and chiral epoxides via enantioselective resolution copolymerization of racemic terminal epoxides with anhydrides, mediated by enantiopure bimetallic complexes in conjunction with a nucleophilic cocatalyst. The chirality of both the axial linker and the diamine backbones of the ligand are responsible for the chiral induction of this kinetic resolution copolymerization process. The catalyst systems exhibit exceptional levels of enantioselectivity with a kinetic resolution coefficient exceeding 300 for various racemic epoxides, affording highly isotactic copolymers (selectivity factors of more than 300) with a completely alternating structure and low polydispersity index. Most of the produced isotactic polyesters are typical semicrystalline materials with melting temperatures in the range from 77 to 160 °C.

A synthesis scheme for synthesizing method (by machine translation)

The invention discloses a synthesis scheme for synthesizing method. The synthesis method of epoxy and ethyl methanol as the starting material, passes through methylation, acidic open-loop, with the benzylamine condensation, and azide reduction acylated five step reaction to obtain the raco amide. The method for synthesis of raw materials are simple and easy to obtain, mild reaction conditions, after treatment is simple, the purity of the product is high, the yield is high. (by machine translation)

Dinuclear salen cobalt complex incorporating Y(OTf)3: enhanced enantioselectivity in the hydrolytic kinetic resolution of epoxides

The activation of inactive Jacobsen's chiral salen Co(ii) (salen = N,N′-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine) compound is attained by dinuclear chiral salen Co(iii)-OTf complex formation with yttrium triflate. The yttrium metal not only displays a promoting effect on electron transfer, but also assists in forming two stereocentres of a Lewis acid complex with Co(iii)-OTf. We found that the binuclear Co-complex significantly enhanced reactivity and enantioselectivity in the hydrolytic kinetic resolution of terminal epoxides compared to its analogous monomer and kinetic data are also consistent with these results.

NEW CHIRAL SALEN CATALYSTS AND METHODS FOR THE PREPARATION OF CHIRAL COMPOUNDS FROM RACEMIC EPOXIDES BY USING THEM

The present invention relates to new chiral salen catalysts and the preparation method of chiral compounds from racemic epoxides using the same. More specifically, it relates to new chiral salen catalysts that have high catalytic activity due to new molecular structures and have no or little racemization of the generated target chiral compounds even after the reaction is completed and can be also reused without catalyst regeneration treatment, and its economical preparation method to mass manufacture chiral compounds of high optical purity, which can be used as raw materials for chiral food additives, chiral drugs, or chiral crop protection agents, etc., using the new chiral salen catalysts.

Hydrolytic kinetic resolution of terminal epoxides catalyzed by novel bimetallic chiral Co (salen) complexes

Novel bimetallic chiral Co (salen) complexes bearing transition-metal salts have been synthesized. The easily prepared complexes exhibited very high catalytic reactivity and enantioselectivity in hydrolytic kinetic resolution (HKR) of racemic terminal epoxides and consequently provided enantiomerically enriched epoxides (up to 99% ee). Copyright Taylor & Francis Group, LLC.

Crotylation versus propargylation: Two routes for the synthesis of the C13-C18 fragment of the antibiotic branimycin

The C13-C18 fragment 3 of the novel antibiotic branimycin was prepared along two highly stereocontrolled routes. The first one uses a standard Roush crotylation protocol, whereas the second one proceeds via an allenyl silane propargylation with unexpected stereochemical consequences, which are discussed in detail.

Synthesis of optically pure terminal epoxide and 1,2-diol via hydrolytic kinetic resolution catalyzed by new heterometallic salen complexes

The inactive chiral (salen)Co complex is easily activated by InCl 3 and TlCl3 Lewis acids by forming heterometallic salen complexes. These complexes show very high catalytic activity for the synthesis of enantiomerically enriched terminal epoxides (>99% ee) and 1,2-diols simultaneously via hydrolytic kinetic resolution. Strong synergistic effects of different Lewis acids, Co-In and Co-Tl, were exhibited in the catalytic process. The system described is very simple and efficient. Copyright Taylor & Francis Group, LLC.

A new dinuclear chiral salen complexes for asymmetric ring opening and closing reactions: Synthesis of valuable chiral intermediates

A new dinuclear chiral Co(salen) complexes bearing group 13 metals have been synthesized and characterized. The easily prepared complexes exhibited very high catalytic reactivity and enantioselectivity for the asymmetric ring opening of epoxides with H2O, chloride ions and carboxylic acids and consequently provide enantiomerically enriched terminal epoxides (>99% ee). It also catalyzes the asymmetric cyclization of ring opened product, to prepare optically pure terminal epoxides in one step. The homogeneous dinuclear chiral Co(salen) have been covalently immobilized on MCM-41. The potential benefits of heterogenization include facilitation of catalyst separation and recyclability requiring very simple techniques. The system described is very efficient.