33208-48-9Relevant academic research and scientific papers
Synthesis of protected glucose derivatives from levoglucosan by development of common carbohydrate protecting group reactions under continuous flow conditions
Marion, Keevan C.,Wooke, Zachary,Pohl, Nicola L.B.
, p. 23 - 29 (2018)
Common carbohydrate protecting group reactions under continuous flow processes are reported in the context of producing partially-protected glucose building blocks from levoglucosan. Benzyl ether protection was demonstrated without the use of NaH using ba
Ring-opening polymerization of new 3-O-branched 1, 6-anhydro glucopyranose di- and trisaccharide monomers
Bai, Chaolumen,Budragchaa, Davaanyam,Yoshida, Takashi
, p. 52 - 60 (2017)
New 3-O-branched 1, 6-anhydro glucopyranose disaccharide monomers, 1, 6-anhydro-2, 4-di-O- benzyl-3-O-(2′, 3′, 4′, 6'-tetra-O-benzyl-α-D-mannopyranosyl)- (LGM 6) and -glucopyranosyl)-β-D- glucopyranose (LGG 7), and a trisaccharide monomer, 1, 6-anhydro-2,
Addressing the Structural Complexity of Fluorinated Glucose Analogues: Insight into Lipophilicities and Solvation Effects
St-Gelais, Jacob,C?té, émilie,Lainé, Danny,Johnson, Paul A.,Giguère, Denis
supporting information, p. 13499 - 13506 (2020/10/02)
In this work, we synthesized all mono-, di-, and trifluorinated glucopyranose analogues at positions C-2, C-3, C-4, and C-6. This systematic investigation allowed us to perform direct comparison of 19F resonances of fluorinated glucose analogues and also to determine their lipophilicities. Compounds with a fluorine atom at C-6 are usually the most hydrophilic, whereas those with vicinal polyfluorinated motifs are the most lipophilic. Finally, the solvation energies of fluorinated glucose analogues were assessed for the first time by using density functional theory. This method allowed the log P prediction of fluoroglucose analogues, which was comparable to the C log P values obtained from various web-based programs.
Synthesis of α-glycosyl thiols by stereospecific ring-opening of 1,6-anhydrosugars
Zhu, Xiangming,Dere, Ravindra T.,Jiang, Junyan,Zhang, Lei,Wang, Xiaoxia
scheme or table, p. 10187 - 10197 (2012/02/05)
Treatment of 1,6-anhydrosugars with commercially available bis(trimethylsilyl) sulfide in the presence of trimethylsilyl triflate led to the formation of α-glycosyl thiols. All the reactions were highly stereoselective and afforded the α-glycosyl thiols in good to excellent yields. By this procedure, a variety of 1,6-anhydrosugars, differing in their sugar units, glycosidic linkages, and protecting group pattern, were converted smoothly into the corresponding α-glycosyl thiols, which could be of great utility in thioglycoside chemistry. It is noteworthy that 1,6-anhydrosugars carrying the 2-O-acyl group and 1,6-anhydrosugar-containing oligosaccharides could also be ring-opened stereospecifically under the same conditions to give rise to the corresponding 1-thiosugars in high yields. Thus, a very concise and efficient access to α-glycosyl thiols of great value was established (Figure presented).
PROSTANOIDS. LVI. USEFUL PROSTAGLANDIN SYNTHONS FROM LEVOGLUCOSAN
Tolstikov, G. A.,Valeev, F. A.,Ibragimova, I. P.,Gaisina, I. N.,Spirikhin, L. V.,Miftakhov, M. S.
, p. 1501 - 1506 (2007/10/02)
(1S,6S,7R,9R)-7,9-Dihydroxy-3-oxabicyclononan-4-one, which is a new chiral synthon for cyclopentanoids, was obtained by intramolecular radical cyclization of methyl 4R,6S-dibenzyloxy-7R-hydroxy-8-acetoxyoct-2E,Z-enoates and subsequent removal of th
α-Glucosidase Inhibitors, 6. - Synthesis of 1,6-Anhydro-D-glucose and -D-galactose Derivatives - Preparation of 1-Deoxynojirimycin
Schmidt, Richard R.,Michel, Josef,Ruecker, Ernst
, p. 423 - 428 (2007/10/02)
Methyl 2,3-di-O-benzyl-D-glucopyranoside (2) is transformed in the presence of p-toluenesulfonic acid and 2,2,2-trichloro- or 2,2,2-trifluoroethanol into the 4-O-unprotected 1,6-anhydropyranose 4.The amount of 1,6-anhydrofuranose 5, formed as a byproduct of this reaction, can be increased by longer reaction times.Similarly, from methyl 2,3-di-O-benzyl-D-galactopyranoside (9) the corresponding 1,6-anhydro compounds 10 and 12 were obtained. 1-Deoxynojirimycin (31) is obtained from the 5-O-unprotected 1,6-anhydroglucofuranose 5 in a few steps.The stereoselectiveintroduction of nitrogen at C-5 is reached by inversion of the configuration of the 5-OH group through oxidation and reduction and subsequent triflate activation for the invertive azide group introduction
Synthesis of the colitose determinant of Escherichia coli O111 and 3,6-di-O-(α-D-galactopyranosyl)-α-D-glucopyranoside
Iversen, Tommy,Bundle, David R.
, p. 299 - 303 (2007/10/02)
The synthesis of two branched trisaccharides, which constitute important elements of enterobacterial lipopolysaccharides are described.The common structural feature of each trisaccharide is α-D-glucopyranoside, upon which branching occurs at the O-3 and O
SYNTHESIS OF A SUBSTITUTED 2,6-DIOXABICYCLOHEPTANE, 1,3-ANHYDRO-2,4,6-TRI-O-BENZYL-β-D-GLUCOPYRANOSE
Ito, Hiroshi,Eby, Ronald,Kramer, Steven,Schuerch, Conrad
, p. 193 - 202 (2007/10/02)
1,3-Anhydro-2,4,6-tri-O-benzyl-β-D-glucopyranose has been synthesized by ring closure of 2,4,6-tri-O-benzyl-α-D-glucopyranosyl chloride via two reaction sequences.The preferable method has allyl 3-O-allyl D-glucopyranoside as key intermediate.This appears to be the first example of an anhydro sugar derivative with the 2,6-dioxabicycloheptane skeleton.
