60989-80-2Relevant academic research and scientific papers
Preparation method of (S)-3-hydroxytetrahydrofuran
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Paragraph 0041, (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.
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.
Effective chemoselective deprotection of 3,4-dimethoxybenzyl ( 3,4DMB) ethers in the presence of benzyl and p-methoxybenzyl (PMB) ethers by phenyliodine(III) bis(trifluoroacetate) (PIFA)
Watanabe, Kazuhiro,Katoh, Tadashi
, p. 5395 - 5397 (2011/10/18)
In this Letter, a selective deprotection of the alcohol protecting 3,4-dimethoxybenzyl (3,4DMB) group is described. The hypervalent iodine(III) reagent phenyliodine bis(trifluoroacetate) (PIFA) is found to be an efficient reagent for the chemos
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%).
