23567-05-7Relevant academic research and scientific papers
One-pot synthesis of cyclic oligosaccharides by the polyglycosylation of monothioglycosides
Someya, Hidehisa,Seki, Takehito,Ishigami, Gota,Itoh, Taiki,Saga, Yutaka,Yamada, Yasuyuki,Aoki, Shin
, (2019/12/14)
Cyclic oligosaccharides such as cyclodextrins (CyDs) have been known as excellent host molecules for the inclusion of various organic guest molecules. The development of new synthetic methods for preparing cyclic oligosaccharides from simple and readily a
Synthesis of unstable 4-benzoyl-1,6-anhydro-3-keto-β-D-mannopyranose via stereoselective photobromination of 2,3-isopropylidene-4-benzoyl-1,6-anhydro-β-D-mannopyranose
Mahdi, Jassem G.,Dawoud, Hanaa M.,Manning, Abigail J.,Lieberman, Harvey F.,Kelly, David R.
, p. 24 - 35 (2019/11/03)
Stereoselective photobromination of 1,6-anhydro-β-D-glucopyranose derivatives occurs at exo-H6. However, photobromination of 4-benzoyl-2,3-isopropylidene-1,6-anhydro-β-D-mannopyranose 6 produced unstable 4-benzoyl-1,6-anhydro-3-keto-β-D-mannopyranose 7. The mechanism of stereoselective oxidation at C-3 could be attributed to the facile radical proton abstraction at C-3, followed by the subsequent bromination of the isopropylidene group, which was subsequently eliminated during the aqueous workup. Thus, the aim of this article is to identify the molecular structure of the unstable compound 7.
PURE HEPTASULFATED DISACCHARIDES HAVING IMPROVED ORAL BIOAVAILABILITY
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Paragraph 0073, (2018/03/09)
Hypersulfated disaccharides with utility in asthma or asthma related disorders are disclosed. The heptasulfated disaccharides administered orally have comparable bioavailability to the intravenous administered dosage form.
Synthesis of 1,6-anhydro sugars catalyzed by silica supported perchloric acid
Chun, Yuexing,Yan, Shiqiang,Li, Xiangpeng,Ding, Ning,Zhang, Wei,Wang, Peng,Li, Ming,Li, Yingxia
experimental part, p. 6196 - 6198 (2011/12/01)
A new and efficient method for the preparation of 1,6-anhydro sugars using silica supported perchloric acid as a catalyst is described. The catalyst is heterogeneous and 1,6-anhydro sugars could be formed within a few minutes with good yields.
Synthesis of pentasaccharide and heptasaccharide derivatives and their effects on plant growth
Liu, Hongmei,Cheng, Shuihong,Liu, Jun,Du, Yuguang,Bai, Zhihui,Du, Yuguo
scheme or table, p. 5634 - 5638 (2010/03/30)
Two oligosaccharide derivatives, β-D-Glcp-(1-6)-β-D-Glcp-(1-6)- β-D-Glcp-(1-6)-β-D-Glcp-(1-4)-α-D-ManpOMe (1) and β-D-Glcp-(1-6)-β-D-Glcp-(1-6)-β-D-Glcp-(1-6)-β-D-Glcp-(1-6) -β-D-Glcp-(1-6)-β-D-Glcp-(1-4)-α-D-ManpOMe (2), have been synthesized efficiently using a convergent glycosylation strategy of 2 + 3 and 2 + 5.1,6-Anhydro-β-D-glucopyranose, which was prepared from cotton pyrolysis, was applied as a key synthon in the synthesis, significantly simplifying the preparation. The bioassay suggested that these two oligosaccharides can both stimulate the growth of maize cultured in liquid medium at a concentration of 3 ppm.
Some aspects of selectivity in the reaction of glycosyl donors
Uriel, Clara,Gomez, Ana M.,Lopez, J. Cristobal,Fraser-Reid, Bert
, p. 665 - 675 (2007/10/03)
Some advantages, disadvantages, and anomalies of various donors in glycosidations are discussed. By studying several two-component donor/acceptor-diol reactions, it is shown that regiopreferences are not very sensitive to the type of donor used. However,
Ferric chloride: A mild and versatile reagent for the formation of 1,6-anhydro glucopyranoses
Miranda, Pedro O.,Brouard, Ignacio,Padrón, Juan I.,Bermejo, Jaime
, p. 3931 - 3934 (2007/10/03)
A novel method for the preparation of 1,6-anhydro glucopyranoses (mono- and disaccharides) utilizing anhydrous FeCl3 as Lewis acid is described. Treatment of methyl 6-O-benzyl and 6-O-p-methoxybenzyl-α/β D-glucopyranosides derivatives with FeCl3 in CH2Cl2 at room temperature and 40°C afforded 1,6-anhydro glucopyranosides in moderate to good yields, through a debenzylation and intramolecular glycosidation in one step. A plausible reaction pathway is proposed.
Highly efficient syntheses of the phytoalexin-elicitor active β- (1→3)-branched β-(1→6)-linked heptaglucose and its dodecyl glycoside
Yi, Yuetao,Zhou, Zhongxuan,Ning, Jun,Kong, Fanzuo,Li, Jianqiang
, p. 491 - 496 (2007/10/03)
A highly efficient method for the synthesis of 3,6-branched gluco-oligosaccharides was developed by using 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose, 2,3,4,6-tetra-O-benzoyl-α-D-glucopyranosyl trichloroacetimidate, and 6-O-acetyl-2,3,4-tri-O-benzoyl-α-
Total synthesis of the antiallergic naphtho-α-pyrone tetraglucoside, cassiaside C2, isolated from Cassia seeds
Zhang, Zhaojun,Yu, Biao
, p. 6309 - 6313 (2007/10/03)
Toralactone 9-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl-(1→3)- P-D-glucopyranosyl-(1-6)-β-D-glucopyranoside (1, cassiaside C2), isolated from Cassia obtusifolia L. and showing strong antiallergic activity, was concisely synthesized employing glycosyl trifluoroacetimidates as glycosylation agents. The unique naphtho-α-pyrone structure of toralactone (5) was constructed by condensation of orsellinate 8 with pyrone 9 in the presence of LDA as developed by Staunton and co-workers. The naphthol of toralactone showed minimal reactivity as an acceptor and was screened with various glycosyl donors. It is finally concluded that sacrifice of an excess amount of the trifluoroacetimidate or trichloroacetimidate donors (6f/6g, 6.0 equiv) in the presence of a catalytic amount of TMSOTf (0.05 and 0.3 equiv, respectively) afforded excellent yields of the coupling product, which was otherwise only a minor product under a variety of conditions examined.
Free radical alkylation of tri-o-benzoyl-6-exo-bromo-levoglucosan: Approaches to the synthesis of okadaic acid
Kelly, David R,Mahdi, Jassem G
, p. 511 - 514 (2007/10/03)
Tri-O-benzoyl-6-exo-bromo-levoglucosan undergoes stereoselective free radical alkylation to give 6-exo-substituted-1,6-anhydrosugars with six contiguous chiral centres.
