78699-85-1Relevant academic research and scientific papers
Regioselective Synthesis of Difluorinated C-Furanosides Involving a Debenzylative Cycloetherification
Delbrouck, Julien A.,Bochatay, Valentin N.,Tikad, Abdellatif,Vincent, Stéphane P.
supporting information, p. 5562 - 5566 (2019/08/01)
A highly regioselective synthesis of valuable gem-difluorinated C-furanosides from unprotected aldoses via a debenzylative cycloetherification (DBCE) reaction induced by diethylaminosulfur trifluoride is descibed. The scope and limitations of this DBCE reaction are described using a series of commercially available pentoses and hexoses to afford, without selective protection/deprotection sequences, the corresponding gem-difluorinated C-furanosides in moderate to good yields.
Efficient and regioselective synthesis of γ-lactone glycosides through a novel debenzylative cyclization reaction
Delbrouck, Julien A.,Tikad, Abdellatif,Vincent, Stéphane P.
supporting information, p. 9845 - 9848 (2018/09/10)
An efficient and regioselective approach for the construction of synthetically important γ-lactone glycosides is reported from unprotected aldoses through a new debenzylative lactonization (DBL) reaction. The scope and limitations of this DBL reaction are described starting from a series of commercially available hexoses (l-fucose, d-galactose, d-glucose) and pentoses (d-arabinose, d-ribose, d-lyxose, d-xylose) to afford the corresponding γ-lactones in good yields and without concomitant δ-lactone formation.
Dapagliflozin impurity synthesis method
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Paragraph 0004; 0024-0026, (2017/03/14)
The invention discloses a dapagliflozin impurity synthesis method. The synthesis method includes: using D-glucose as a raw material; subjecting the D-glucose to reactions of aldehyde group protection through ethanethiol, benzyl group adding, ethanethiol removal, condensation and benzyl group removal to obtain dapagliflozin impurities. A basis is provided for study of dapagliflozin related substances.
A Catalytic Deprotection of S,S-, S,O- and O,O-Acetals Using Bi(NO3)3·5 H2O under Air
Komatsu, Naoki,Taniguchi, Azusa,Wada, Shinobu,Suzuki, Hitomi
, p. 473 - 480 (2007/10/03)
S,S-Acetals are smoothly deprotected with air in the presence of a catalytic amount of Bi(NO3)3·5 H2O (1-50 mol %) under ambient conditions to regenerate the original carbonyl compounds in good to excellent yield. This mild, simple, and environmentally benign system is successfully applied to the deprotection of S,O- and O,O-acetals and is compatible with various functional groups. From the mechanistic study of the reaction, the catalytic cycle is considered to be composed of the following four steps: (1) the nitrososulfonium ion of the S,S-acetal is formed by attack of nitrosonium ion (NO+) generated from Bi(NO3)3·5 H2O through the equilibrium wth NO2, (2) the nitrososulfonium ion is hydrolyzed to afford the hemithioacetal and thionitrite, (3) the hemithioacetal collapses to the original carbonyl compound and thiol, which is oxidized by NO+ to give disulfide and NO via thionitrite, and (4) the NO captures molecular oxygen from air to regenerate NO2.
Back to the sugars: A new enantio and diastereocontrolled route to hexoses from furfural
Takeuchi, Miwako,Taniguchi, Takahiko,Ogasawara, Kunio
, p. 341 - 354 (2007/10/03)
An integrated enantio and diastereocontrolled route to both enantiomers of the eight possible hexoses has been explored starting from furfural, by employing the Sharpless asymmetric dihydroxylation as a key step. At the present, a route to six of the eight possible hexoses has been established. The present synthesis may be taken as a reversion of the sugar-originated furfural to the sugars via a levoglucosenone, a pyrolysate of cellulose, type intermediate.
SHORT SYNTHESIS OF C-ARYL-GLUCOPYRANOSIDES OF THE PAPULACANDIN TYPE
Schmidt, Richard R.,Frick, Wendelin
, p. 7163 - 7170 (2007/10/02)
The aryllithium species 5a-A and 5b-A generated via bromine/lithium exchange reaction, afforded with the per-O-benzylated D-glucose 6 the adducts 9a,b; subsequent oxidation furnished the corresponding ketones 10a,b.Compound 10a was also obtained from 5a-A
Synthesis of Oligosaccharides Corresponding to the Common Polysaccharide Antigen of Group B Streptococci
Pozsgay, Vince,Jennings, Harold J.
, p. 4042 - 4052 (2007/10/02)
To facilitate mapping of the immunodominant region of the common polysaccharide antigen of group B streptococci, tetrasaccharide 1-O--α-rhamnopyranosyl>-D-glucitol (2) was synthesized in a stepwise fasion
