10548-53-5Relevant academic research and scientific papers
A method for one-step synthesis of peracetylated-alpha-O-benzyl saccharides
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Paragraph 0081; 0083-0085, (2018/12/02)
The invention relates to the technical field of chemical synthetic methods of saccharides, and particularly relates to a method for one-step synthesis of peracetylated-alpha-O-benzyl saccharides. A peracetylated monosaccharide is adopted as a donor, benzyl alcohol is adopted as a receptor, 1,2-dichloroethane is adopted as a reaction solvent, a peracetylated-alpha-O-benzyl saccharide is synthesizedthrough reaction under catalysis of ferric chloride anhydrous, and the reaction temperature is 10-40 DEG C. The method is high in regional universality, low in receptor consumption, mild in reactionconditions, high in yield, and high in stereoselectivity and can be used for large-scale production of target products. The catalyst is nontoxic and easily available.
Stereoselective Syntheses of α-Glucuronides Using Dehydrative Glycosylation
Koto, Shinkiti,Miura, Teruhisa,Hirooka, Motoko,Tomaru, Aya,Iida, Mika,Kanemitsu, Masanori,Takenaka, Kazuhiro,Masuzawa, Shinichi,Miyaji, Saeko,Kuroyanagi, Naoko,Yagishita, Miki,Zen, Shonosuke,Yago, Kazuo,Tomonaga, Fumiya
, p. 3247 - 3259 (2007/10/03)
Methyl and benzyl 2,3,4-tri-O-benzyl-D-glucopyranuronates, prepared from D-glucurono-6,3-lactone, afforded selectively the corresponding α-glucopyranosiduronates by the aid of the condensing reagent system composed of p-nitrobenzenesulfonyl chloride, silver trifluoromethanesulfonate, and triethylamine. Using this method, O-α-D-glucopyranuronosyl-(1→3)-O-α-L-arabinofuranosyl- (1→3)-D-xylopyranose, one of the minimal component units in the structure of plantago-mucilage A from the seeds of Plantago asiatica Linne constituting a Chinese medicine : chegianzi [HU~P].
Anomeric O-Alkylation, 11. Anomeric O-Alkylation of O-Unprotected Hexoses and Pentoses - Convenient Synthesis of Decyl, Benzyl, and Allyl Glycosides
Klotz, Wolfgang,Schmidt, Richard R.
, p. 683 - 690 (2007/10/02)
The base-promoted reaction of O-unprotected aldoses 1-6 with didecyl sulfate in DMPU affords decyl glycosides 1aα-6aα and 1aβ, 3aβ-6aβ in good overal yields.Similarly, the treatment of O-unprotected hexoses 1-4 and pentoses 5 and 6 with benzyl bromide and allyl bromide yields after subsequent O-acetylation monosaccharides 1cα-6cα, 1cβ, 3cβ-6cβ and 1dα-6dα, 1dβ, 3dβ-6dβ, respectively.The regio- and stereoselectivity in these reactions was determined by 1H-NMR spectroscopic data of the O-acetylated derivatives.Key Words: Aldoses, O-unprotected, glycoside formation / Anomeric oxides, alkylation / Alkylating agents, didecyl sulfate, benzyl bromide, allyl bromide / α-D-galacto-furanosides
4-O-β-D-Galactopyranosyl-D-xylose: A new synthesis and application to the evaluation of intestinal lactase
Rivera-Sagredo,Fernandez-Mayoralas,Jimenez-Barbero,Martin-Lomas,Villanueva,Aragon
, p. 129 - 135 (2007/10/02)
4-O-β-D-Galactopyranosyl-D-xylose (2) was prepared from benzyl 2,3-O-isopropylidene-β-D-xylopyranoside by glycosylation with 2,3,4,6-tetra-O-benzoyl-α-D-galactopyranosyl bromide and subsequent deprotection. Compound 2 was hydrolyzed in vitro by intestinal lactase; the V(max) was 25% of that with lactose and the K(m) was 370 mM (cf. 27 mM for lactose). Oral administration of 2 to suckling rats led to urinary excretion of D-xylose which could be estimated colorimetrically. 4-O-β-D-Galactopyranosyl-D-xylose (2) was prepared from benzyl 2,3-O-isopropylidene-β-D-xylopyranoside by glycosylation with 2,3,4,6-tetra-O-benzoyl-α-D-galactopyranosyl bromide and subsequent deprotection. Compound 2 was hydrolyzed in vitro by intestinal lactase; the Vmax was 25% of that with lactose and the Ktu was 370mM (cf. 27mM for lactose). Oral administration of 2 to suckling rats led to urinary excretion of D-xylose which could be estimated colorimetrically.
