82130-73-2Relevant academic research and scientific papers
Preparation method of (S)-3-hydroxytetrahydrofuran
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Paragraph 0040, (2018/06/15)
The invention discloses a preparation method of (S)-3-hydroxytetrahydrofuran. The problems that butantriol is difficult to separate in the production process, the yield is not high and the impurity content and the isomer content of the products are high are mainly solved. The preparation method of (S)-3-hydroxytetrahydrofuran comprises the following steps: under the existence of sulfoxide chloride, malic acid reacts with methanol to generate a compound II; under the existence of silver oxide, performing reaction on the compound II and benzyl bromide to generate a compound III; reducing the compound III by sodium borohydride to generate a compound IV; performing dehydration and ring closing on the compound IV by p-toluenesulfonic acid to generate a compound V; and taking palladium carbon asa catalyst and performing hydrogen reduction treatment on the compound V to obtain the product. The method is simple in aftertreatment and environment-friendly; the yield of the products is increasedby 80 percent or more, the purity is more than 99.5 percent and the chiral purity is more than 99.2 percent; and the method is suitable for industrialized production. (The formulas are as shown in the description).
Intramolecular functional group differentiation as a strategy for the synthesis of bridged bicyclic β-amino acids
Tymtsunik, Andriy V.,Kokhan, Serhii O.,Ivon, Yevhen M.,Komarov, Igor V.,Grygorenko, Oleksandr O.
, p. 22737 - 22748 (2016/03/26)
Differentiation of identical electrophilic functional groups (carboxylates) by a strategically placed internal nucleophile (an amino group) in cyclic precursors was used as a key general approach to functionalized azabicyclic scaffolds. The utility of the method was demonstrated by the synthesis of three bicyclic β-amino acids (analogues of nipecotic acid), which were prepared in good yields and on a relatively large scale.
Design and concise synthesis of gem-difluoromethylenated analogue of 7-epi-castanospermine
Jiang, Xin-Yi,Xu, Xiu-Hua,Qing, Feng-Ling
, p. 1115 - 1120 (2014/08/18)
A novel gem-difluoromethylenated castanospermine analogue B was designed and synthesized, starting from 3-bromo-3,3-difluoropropene and L-(-)-malic acid. The key steps involve substitution cyclization reaction and RCM reaction to construct the aza fused b
Synthesis of 3-substituted tetrahydrofuran and 4-substituted tetrahydropyran derivatives by cyclization of dicarboxylic acids with InBr 3/TMDS
Pehlivan, Leyla,Metay, Estelle,Delbrayelle, Dominique,Mignani, Gerard,Lemaire, Marc
supporting information; experimental part, p. 4689 - 4693 (2012/09/22)
An efficient reduction followed by cyclization of diacid compounds with the InBr3/TMDS system is reported. This system allows the formation of five- and six-membered ring ethers substituted in the 3- or 4-position. Copyright
A chiral pool based approach to antipodes of α-cuparenone
Chavan, Subhash P.,Lasonkar, Pradeep B.
, p. 1496 - 1500,5 (2012/12/12)
A synthetic route to both antipodes of α-cuparenone was achieved from the readily available chiral pool starting material l-malic acid and involved cyclopentannulation as the key step.
A chiral pool based approach to antipodes of α-cuparenone
Chavan, Subhash P.,Lasonkar, Pradeep B.
, p. 1496 - 1500 (2013/01/15)
A synthetic route to both antipodes of α-cuparenone was achieved from the readily available chiral pool starting material l-malic acid and involved cyclopentannulation as the key step.
Investigating the role of the hydroxyl groups of substrate erythrose 4-phosphate in the reaction catalysed by the first enzyme of the shikimate pathway
Tran, David,Pietersma, Amy L.,Schofield, Linley R.,Rost, Matthias,Jameson, Geoffrey B.,Parker, Emily J.
supporting information; scheme or table, p. 6838 - 6841 (2012/01/03)
3-Deoxy-d-arabino-heptulosonate 7-phosphate (DAH7P) synthase catalyses the first step of the shikimate pathway, which is responsible for the biosynthesis of aromatic amino acids in microorganisms and plants. This enzyme catalyses an aldol reaction between phosphoenolpyruvate and d-erythrose 4-phosphate to generate DAH7P. Both 2-deoxyerythrose 4-phosphate and 3-deoxyerythrose 4-phosphate were synthesised and tested as alternative substrates for the enzyme. Both compounds were found to be substrates for the DAH7P synthases from Escherichia coli, Pyrococcus furiosus and Mycobacterium tuberculosis, consistent with an acyclic mechanism for the enzyme for which neither C2 nor C3 hydroxyl groups are required for catalysis. The enzymes all showed greater tolerance for the loss of the C2 hydroxyl group than the C3 hydroxyl group.
A convergent synthesis of the [4.4]-spiroacetal-γ-lactones cephalosporolides e and F
Brimble, Margaret A.,Finch, Orla C.,Heapy, Amanda M.,Fraser, John D.,Furkert, Daniel P.,O'Connor, Patrick D.
experimental part, p. 995 - 1001 (2011/03/19)
A short convergent synthesis of the fungal metabolites cephalosporolides E and F is reported. The key step makes use of a chelation-controlled Mukaiyama aldol reaction to access the key acyclic spiroacetal precursor with the required syn stereochemistry.
Asymmetric synthesis of the cyclopentanones related to NCS and N1999A2 antitumor antibiotics
Bertus, Philippe,Zhang, Jing-Heng,Sir, Geoffroy,Weibel, Jean-Marc,Pale, Patrick
, p. 3391 - 3395 (2007/10/03)
Optically pure protected mono- or dihydroxylated cyclopentanones, precursors for the core of the antitumor antibiotics NCS and N1999A2, 1 and 2, were obtained in six to eight steps with excellent overall yields (up to 52%).
One-Pot Generation and Conversion of Trichloroacetimidates for the Racemization-Free Allylation and Benzylation of α-Hydroxyesters and the Enantiopure Synthesis of a Chiral Diglycole
Christoffers, Jens,R??ler, Ulrich
, p. 654 - 658 (2007/10/03)
Ο-Allylations and Ο-benzylations of α-hydroxy esters (3a-3c) are performed without racemization. The reagents applied, Ο-allyl- and Ο-benzyltrichloroacetimidate (5a, 5b) are prepared and converted in a one-pot-procedure. After protection by benzylation (S)-(-)-ethyl lactate (3a) is converted by a sequence of carbonyl reduction, alcohol activation, ether formation, and deprotection to the optically active diglycole derivative 1a.
