77312-71-1

Upstream product

• 87-91-2 diethyl (2R,3R)-tartrate 
• 100-39-0 benzyl bromide 
• 21066-72-8 diethyl tartrate 

Downstream Products

• 138794-81-7 (2R,3R)-2,3-bis(benzyloxy)tartaric acid 
• 133519-75-2 (2R,3R)-2,3-Bis-benzyloxy-succinamide 
• 113427-43-3 1,4-di-O-benzyl-L-threitol 
• 131379-07-2 (2R,3S)-2,3-bis(benzyloxy)-4-((tert-butyldimethylsilyl)oxy)butanal 
• 321566-90-9 (3R,4R)-3,4-bis(benzyloxy)-1-(4-methoxybenzyl)-pyrrolidine-2,5-dione 
• 944543-94-6 (3R,4S,5S)-5-benzyloxymethyl-3,4-dibenzyloxy-1-(4-methoxybenzyl)-pyrrolidin-2-one 
• 944543-95-7 (3R,4S,5S)-5-benzyloxymethyl-3,4-dibenzyloxy-pyrrolidin-2-one 
• 100806-55-1 (2S,3S,4S)-2-benzyloxymethyl-3,4-dibenzyloxy-pyrrolidin 
• 869627-61-2 benzyl 4-{(3R,4R)-3,4-bis(benzyloxy)-2,5-dioxopyrrolidin-1-yl}-benzoate 
• 97506-01-9 (3R,4R)-3,4-bis(benzyloxy)-3,4-dihydro-2,5-furandione 
• 113321-60-1 (2S,3S)-(+)-1,4-dibromo-2,3-bis(phenylmethoxy)butane 
• 113303-29-0 (2S,3S)-(+)-2,3-bis(phenylmethoxy)-1,4-bis<<(4-methylphenyl)sulfonyl>oxy>butane 
• 113321-59-8 (2R,3R)-(-)-2,3-bis(phenylmethoxy)-1,4-bis<<(4-methylphenyl)sulfonyl>oxy>butane 
• 403670-55-3 2,3-bis(benzyloxy)-1,3-butadiene 

Relevant academic research and scientific papers

One-pot cascade synthesis of azabicycles via the nitro-Mannich reaction and N -alkylation

A one-pot, metal-free process for the synthesis of azabicycles is developed. The key transformations involved a cascade of double intramolecular cyclizations via the nitro-Mannich reaction and N-alkylation, providing various ring systems of azabicycles in

C4 branched polyhydroxy pyrrolidine compound and preparation method and application thereof

The invention relates to the field of glycosidase inhibitors, in particular to a C4 branched polyhydroxy pyrrolidine compound and a preparation method and application thereof. The structure of the C4 branched polyhydroxy pyrrolidine compound is as is shown in the description. The C4 branched polyhydroxy pyrrolidine compound is good in glycosidase inhibition activity and has potential medicinal value.

Gold(I)-Catalyzed Domino Cyclizations of Diynes for the Synthesis of Functionalized Cyclohexenone Derivatives. Total Synthesis of (-)-Gabosine H and (-)-6-epi-Gabosine H

1,6-Diynes with a t-butylcarbonate group in the propargylic position undergo gold(I)-catalyzed domino-cyclization which affords α-hydroxycyclohexenones. The described sequence can be applied on functionalized, highly oxygenated substrates, as examplified

Practical synthesis of trans-dihydroxybutyrolactols as chiral C4 building blocks and their application to the synthesis of polyhydroxylated alkaloids

Practical syntheses of trans-dihydroxybutyrolactols 2a, 2b and 2c from inexpensive chiral pool compounds l-ascorbic, d- and l-tartaric acid have been achieved on a multigram-scale. The synthetic applications of these chiral building blocks have been demonstrated in the efficient total or formal synthesis of polyhydroxylated alkaloids (+)-lentiginosine and (-)-deacetylanisomycin in concise routes. The Royal Society of Chemistry 2013.

Asymmetric synthesis of gem-difluoromethylenated dihydroxypyrrolizidines and indolizidines

An asymmetric synthesis of gem-difluoromethylenated dihydroxypyrrolizidines and indolizidines is described. The fluoride-catalyzed nucleophilic addition of PhSCF2SiMe3 (1) to chiral imides was achieved in satisfactory yields to provide mixtures of syn- and anti-isomers 6-9 with moderate to good diastereoselectivities. Reductive cleavage of the phenylsulfanyl group followed by intramolecular radical cyclization of the syn-isomers 6-9 occurred under refluxing conditions to afford the corresponding gem-difluoromethylenated 1-azabicyclic compounds 10-13 in moderate yields as a separable mixture of cis- and trans-isomers. The cis-isomers of compounds 10 and 12 and trans-13 were readily transformed to gem-difluoromethylenated dihydroxypyrrolizidines 20 and 27 and indolizidine 28, respectively, by reductive cleavage of the hydroxyl group and organometallic addition followed by hydrogenolysis.

A study on the racemization step in the synthesis of pyrrolidinols via cyclic α-hydroxyimides

Analytical HPLC methods for the determination of the enantiomeric excess of N-protected malimides 1 as well as the corresponding pyrrolidinol 5 and tartarimides 2 and 3 have been established. On this basis, a study to reveal the racemization step in the synthesis of pyrrolidinols from α-hydroxyacids, via chiral cyclic α-hydroxyimides, has been undertaken. It was confirmed that the known, one-step method for the synthesis of the N-protected chiral cyclic imides from α-hydroxydiacids proceeded with little racemization, and partial racemization has been proven to occur during the reduction of the resultant imide 1a with LAH to yield the corresponding pyrrolidinol 5. Conditions have been defined in order to avoid racemization in the LAH reduction step.

Hydrogen-bonding sheets in crystals for chirality recognition: synthesis and application of (2S,3S)-2,3-dihydroxy- and (2S,3S)-2,3-dibenzyloxy-1,4-bis(hydroxyamino)butanes

Two enantiopure bis(hydroxyamino) compounds were successfully prepared from dialkyl tartrate by a chiral-pool method and applied as basic resolving agents in the enantioseparation of 2-arylpropanoic acids and arylglycolic acids. (2S,3S)-2,3-Dihydroxy-1,4-bis(hydroxyamino)butane (2S,3S)-1a could moderately recognize the chirality of the 2-arylpropanoic acids, while (2S,3S)-2,3-dibenzyloxy-1,4-bis(hydroxyamino)butane (2S,3S)-1b could not due to the low crystallinity of both the corresponding diastereomeric salts. On the other hand, (2S,3S)-1b showed a similar chirality-recognition ability for the arylglycolic acids. The ability of (2S,3S)-1b was different from those generally observed for widely used primary amine-type resolving agents with regard to the relationship between the resolution efficiency and the similarity in the relative molecular length of a resolving agent and a target racemate. The X-ray crystallographic analyses of the less-soluble diastereomeric salts revealed that in the salts (2S,3S)-1a formed a supramolecular sheet, of which the distance was variable to make the resultant dissymmetric space fit to the shape of the target acids, and that (2S,3S)-1b was constructed from a robust supramolecular sheet, consisting of hydrogen-bonding 21 columns, with the participation of the hydroxy group of the arylglycolic acids. These X-ray crystallographic analyses also suggested that for the formation of a supramolecular sheet, the coexistence of two hydroxyamino groups is essential.

A versatile approach to pyrrolidine azasugars and homoazasugars based on a highly diastereoselective reductive benzyloxymethylation of protected tartarimide

A highly diastereoselective synthesis of enantio-enriched all trans-3,4-dibenzyloxyl-5-benzyloxymethyl-2-pyrrolidinone 13a was developed based on SmI2-mediated benzyloxymethylation of O,O′-dibenzyltartarimide. The versatility of 13a and its antipode as the key building blocks for the asymmetric synthesis of pyrrolidine azasugars and homoazasugars has been demonstrated by elaborating them into naturally occurring DAB 1 (1), LAB 1 (2), N-hydroxyethyl-DAB 1 (4), 6-deoxy-DMDP 7, and 5-epi-radicamine B 36 as well as the reductive ring-opening product 35.

Synthesis of new chiral ionic liquids from natural acids and their applications in enantioselective Michael addition

Two kinds of novel chiral ionic liquids based on imidazolium have been synthesized from chiral pool by a simple and straightforward procedure in good overall yields (44-60%). The application of CILs as reaction media in the enantioselective Michael additi

Design of branched and chiral solvatochromic probes: Toward quantifying polarity gradients in dendritic macromolecules

(Chemical Equation Presented) A pair of chiral, branched monomer building blocks, consisting of a solvatochromic probe and a spectroscopically inactive volume dummy, has been developed. The probe can selectively be excited, and its fluorescence characteristics provide information about local polarity. Incorporation of these monomers into high-generation polyester dendrimers should enable a detailed investigation of the polarity/density profile in dendritic architectures and ultimately allow for the realization of energy gradients from one chromophore building block only.