51096-08-3

Upstream product

• 4841-84-3 dimethyl cis-1,2,3,6-tetrahydrophthalate 
• 4841-85-4 cis-4-cyclohexene-1,2-dicarboxylic acid diethyl diester 
• 627-63-4 fumaryl dichloride 
• 106-99-0 buta-1,3-diene 
• 77-79-2 3-Sulfolene 
• 110-17-8 (2E)-but-2-enedioic acid 
• 6915-18-0 2-butenedioic acid 
• 623-91-6 diethyl Fumarate 
• 17673-68-6 dimethyl trans-cyclohex-4-ene-1,2-dicarboxylate 
• 189683-61-2 dimenthyl trans-cyclohex-4-ene-1,2-dicarboxylate 
• 122518-87-0 bis((S)-methyl L-lactate) fumarate 
• 88-98-2 trans-cyclohex-4-ene-1,2-dicarboxylic acid 

Downstream Products

• 15679-27-3 (4S,5S)-4,5-bis(hydroxymethyl)cyclohexene 
• 50987-15-0 (1S,2S)-(+)-trans-cyclohex-4-ene-1,2-dicarboxylic acid 
• 935-79-5 cis-1,2,3,6-tetrahydrophthalic anhydride 
• 4841-84-3 dimethyl cis-1,2,3,6-tetrahydrophthalate 
• 31139-02-3 (1R,6S)-6-methoxycarbonyl-3-cyclohexene-1-carboxylic acid 
• 67337-17-1 ((1S,6S)-6-(benzyloxymethyl)cyclohex-3-enyl)methanol 
• 66251-11-4 Toluene-4-sulfonic acid (1S,6S)-6-benzyloxymethyl-cyclohex-3-enylmethyl ester 
• 66251-12-5 ((1R,6S)-6-Benzyloxymethyl-cyclohex-3-enyl)-acetic acid 
• 67312-13-4 ((1R,6S)-6-Benzyloxymethyl-cyclohex-3-enyl)-acetonitrile 
• 231278-96-9 4-[3-acetylamino-5-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-4-(3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-5-benzyloxy-cyclohexane-1,2-dicarboxylic acid di-tert-butyl ester 
• 231278-93-6 (1S,2S,4R,5S)-4-Benzyloxy-5-hydroxy-cyclohexane-1,2-dicarboxylic acid di-tert-butyl ester 
• 221344-11-2 (1S,2S,4R,5S)-4-[(2R,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-methoxycarbonyl-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-yloxy]-5-hydroxy-cyclohexane-1,2-dicarboxylic acid di-tert-butyl ester 
• 371975-08-5 (1S,2S,4R)-4-(tert-butyldimethylsilyloxy)-5-oxocyclohexane-1,2-dicarboxylic acid di-tert-butyl ester 
• 371975-06-3 (1S,2S,4R)-4-benzyloxy-5-oxocyclohexane-1,2-dicarboxylic acid di-tert-butyl ester 

Relevant academic research and scientific papers

Improved synthesis of both enantiomers of trans-cyclohex-4-ene-1,2- dicarboxylic acid

A facile synthesis of both enantiomers of trans-cyclohex-4-ene-1,2- dicarboxylic acid on a multigram scale, that starts from inexpensive, commercially available compounds, is described.

RECYCLABLE POLYMERS BASED ON RING-FUSED GAMMA-BUTYROLACTONES

The invention discloses a class of new polymers, trans-ring-fused poly(4-hydroxybutyrate)s (RF-P4HB) that exhibit a unique set of properties, including robust thermal stability and mechanical strength, quantitative recyclability to the building block monomers via thermolysis and/or chemical catalysis, and convenient production from the chemical ring-opening polymerization under ambient temperature and pressure. Another unique property is the formation of crystalline stereocomplexed polymers with high melting temperature upon mixing the two enantiomeric RF-P4HB chains via stereocomplexing co-crystallization. This invention also provides the corresponding ring-fused lactone monomer structures that enable the synthesis of the RF-P4HB polymers, through trans-fusing of rings to the parent γ-butyrolactone ring. Furthermore, a polymerization or copolymerization process for the synthesis of RF-P4HB polymers and copolymers is disclosed.

PROCESS FOR PREPARING BENZISOTHIAZOL-3-YL-PEPERAZIN-L-YL-METHYL-CYCLO HEXYL-METHANISOINDOL-1,3-DIONE AND ITS INTERMEDIATES

The present invention discloses process for preparing benzisothiazol-3-yl- piperazin-l-yl-methyl-cyclo hexyl-methanisoindol-l,3-dione and intermediates thereof.

Asymmetric Diels-Alder reaction of 1,3-butadienes with (-)-dimenthyl fumarate in the presence of BBr3 and BBr3·OEt 2

Asymmetric synthesis of substituted cyclohexenes was performed by [4+2]-cycloaddition of (-)-dimenthyl fumarate to 1,3-butadienes in the presence of BBr3 and BBr3·OEt2. The latter are efficient catalysts for this reaction.

Sugar mimics: An artificial receptor for cholera toxin

The paper describes the pseudosugar 2 [Galβ1-3GalNAcβ1-4(NeuAcα2- 3)DCCHD], a high affinity binder of cholera toxin (CT). The molecule was designed using molecular modeling techniques to mimic the natural CT membrane receptor, ganglioside GM1. The central residue of GM1, a 3,4-disubstituted galactose unit, was recognized as the ganglioside scaffold element and substituted with a conformationally locked cyclohexanediol (DCCHD). DCCHD was synthesized in enantiopure form using enantioselective Diels Alder methodology and regioselectively α-sialylation at the equatorial position. Glycosylation with a Galβ(1-3)-GalNAc donor completed the synthesis of 2. The solution structure of 2 and its binding ability to CT were found to be analogous to those of the GM1 oligosaccharide.

Synthesis of a pseudo tetrasaccharide mimic of ganglioside GM1

The pseudo tetrasaccharide 2 was designed to mimic ganglioside GM1, the membrane receptor of both the cholera toxin and of the heat-labile toxin of E. coli. Compound 2 retains the Gal and Neu5Ac recognition determinant of GM1 and uses as the scaffold elem

Preparations and Crystal Structures of the 2-Oxides of Some Octahydro-3,2,1-benzoxathiazines and Octahydro-2H-3,1,2-benzoxazaphosphorines

The cis- and trans-fused 1-benzyl-1,4,4a,5,6,7,8,8a-octahydro-3,2,1-benzoxathiazine 2-oxides and cis- and trans-fused 1-benzyl-2-phenyl-1,4,4a,5,6,7,8,8a-octahydro-2H-3,1,2-benzoxazaphosphorine 2-oxides have been prepared from the cis- and trans-2-benzylaminocyclohexanemethanols and their structures have been determined by n.m.r. and crystallographic methods.

STEREOCHEMICAL STUDIES 83. SATURATED HETEROCYCLES 76. PREPARATION AND CONFORMATIONAL STUDY OF PARTIALLY SATURATED 3,1-BENZOXAZINES, 3,1-BENZOXAZIN-2-ONES AND 3,1-BENZOXAZINE-2-THIONES

The cis- and trans-2-amino-4-cyclohexene-1-carboxylic acids 1 and 3 react with imidates to give the condensed-skeleton, bicyclic cis- and trans-pyrimidin-4-ones 8 and 9.The amino acids 1 and 3 were reduced to the cis- and trans-1,3-aminoalcohols 6 and 7, which were cyclized by means of imidates to the bicyclic tetrahydro-4H-3,1-benzoxazines 10 and 11, or were converted, via the corresponding carbamates 14 and 15 into the tetrahydro-4H-3,1-benzoxazin-2(1H)-ones 16 and 17.The 2-thioxo analogues 18 and 19 were prepared by cyclization of the dithiocarbamates obtained from the aminoalcohols 6 and 7 by treatment with carbon disulphide.The trans-aminoalcohol 7 and its saturated analogue reacted with p-chlorobenzaldehyde to furnish the hexahydro 13 and octahydro-4H-3,1-benzoxazine 13a, respectively. 1H and 13C NMR studies showed that, similarly to the earlier-investigated analogues containing oxygen or unsubstituted nitrogen at position 1, the synthesized cis isomers 8, 10, 16 and 18 occurred as the preferred conformer in the heterocyclic twist inverse form of N-inside type (quasiaxal C6-N bond) (B).In the trans isomers containing a saturated C-2 atom (13 and 13a), H-2 and H-6 are in cis relative positions.

Enantioselectivity of the Microsomal Epoxide Hydrolase Catalyzed Hydrolysis of trans-4,5-Dimethyl-1,2-epoxycyclohexane

The hydrolysis of the racemic and enantiomeric forms of trans-4,5-dimethyl-1,2-epoxycyclohexane, catalyzed by rabbit liver microsomal epoxide hydrolase (EH), has been investigated to clarify further the mechanism of enantioselection by this enzyme.Both ac