- 5,5-Difluoro- and 5-Fluoro-5-methyl-hexose-based C-Glucosides as potent and orally bioavailable SGLT1 and SGLT2 dual inhibitors
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(2S,3R,4R,5S,6R)-2-Aryl-5,5-difluoro-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4-diols and (2S,3R,4R,5S,6R)-2-aryl-5-fluoro-5-methyl-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4-diols were discovered as dual inhibitors of sodium glucose co-transporter proteins (
- Demarest, Keith,Du, Fuyong,Gaul, Michael D.,Kuo, Gee-Hong,Liang, Yin,Xu, Guozhang,Xu, June Zhi
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- 5,5-DIFLUORO- AND 5-FLUORO-5-METHYL-C-GLYCOSIDE DERIVATIVES USEFUL AS DUAL SGLT1 / SGLT2 MODULATORS
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The present invention is directed to 5,5-difluoro- and 5-fluoro-5-methyl-C-glycoside derivatives, pharmaceutical compositions containing them and their use in the treatment of disorders and conditions modulated by SGLT activity, more particularly dual SGLT1/2 activity.
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- BENZOCYCLOBUTANE DERIVATIVES USEFUL AS DUAL SGLT1/SGLT2 MODULATORS
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The present invention is directed to benzocyclobutane derivatives, pharmaceutical compositions containing them and their use in the treatment of disorders and conditions modulated by SGLT activity, more particularly dual SGLT1/2 activity. More particularly, the compounds of the present invention are useful in the treatment of for example, Type II diabetes mellitus, Syndrome X, and complications and symptoms associated with said disorders.
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- Synthesis of the Tetrasaccharide Repeating Unit from Acinetobacter baumannii Serogroup O18 Capitalizing on Phosphorus-Containing Leaving Groups
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The first convergent synthesis of the tetrasaccharide repeating unit of the polymeric O antigen isolated from Acinetobacter baumannii serogroup O18 has been achieved. The ManNAcβ1→4Gal and GalNAcβ1→3Gal units were successfully obtained through β-selective
- Arihara, Ryoichi,Kakita, Kosuke,Yamada, Kazuhiro,Nakamura, Seiichi,Hashimoto, Shunichi
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p. 4278 - 4288
(2015/05/13)
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- Tin-mediated regioselective benzylation and allylation of polyols: Applicability of a catalytic approach under solvent-free conditions
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The first catalytic version of the stannylene-mediated benzylation and allylation of polyols is reported. The methodology is based on a simple solvent-free protocol that significantly advances, in terms of both experimental ease and synthetic scope, the a
- Giordano, Maddalena,Iadonisi, Alfonso
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p. 213 - 222
(2014/01/17)
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- An easy and versatile approach for the regioselective De-O-benzylation of protected sugars based on the I2/Et3SiH combined system
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The use of cheap and easy to handle reagents, such as I2 and Et3SiH, at low temperature allows the regioselective removal of benzyl protecting groups from highly O-benzylated carbohydrates. The observed regioselectivity is dependent
- Pastore, Antonello,Valerio, Silvia,Adinolfi, Matteo,Iadonisi, Alfonso
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experimental part
p. 5881 - 5889
(2011/06/24)
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- Direct formation of β-glycosides of N-acetyl glycosamines mediated by rare earth metal triflates
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A direct, mild and efficient protocol for the preparation of β-glycosides of N-acetyl glucosamine (GlcNAc) and N-acetyl galactosamine (GalNAc) has been developed using peracetylated β-GlcNAc and β-GalNAc as donors. All rare Earth metal triflate promoters
- Christensen, Helle,Christiansen, Mira Steinicke,Petersen, Jette,Jensen, Henrik Helligso
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supporting information; experimental part
p. 3276 - 3283
(2009/02/05)
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- Synthesis of 1-deoxyhept-2-ulosyl-glycono-1,5-lactone utilizing α-selective O-glycosidation of 2,6-anhydro-1-deoxy-d-hept-1-enitols
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A series of 1-deoxy-heptulo-2-pyranosyl-glycono-1,5-lactones were synthesized utilizing completely α-selective O-glycosidation of heptenitols. Anomeric configuration of the products was confirmed by 3JC,H coupling measurement and X-ray crystal structural analysis. The benzyl-protected ketosyl saccharides were partly unstable, and glycosidic linkage was prone to cleave under the usual debenzylation conditions. To prevent this, we surveyed various additives for the Pd-catalyzed hydrogenation reaction and found that basic alumina was the most effective.
- Namme, Rie,Mitsugi, Takashi,Takahashi, Hideyo,Shiro, Moto,Ikegami, Shiro
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p. 9183 - 9192
(2007/10/03)
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- Syntheses of O-β-D-mannosyl-(1 → 4)-O-α-D-mannosyl-(1 → 3)-L-rhamnose and O-(2-acetamido-2-deoxy-β-D-mannosyl)-(1 → 4)-O-α-D-galactosyl-(1 → 4)-D-galactose via in-situ-activating glycosylation using 2-O-acetyl-3,4,6-tri-O-benzyl-D-glucose
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O-β-D-Mannopyranosyl-(1 → 4)-O-α-D-mannopyranosyl-(1 → 3)-L-rhamnopyranose, a trisaccharide including a repeating unit of the O-specific polysaccharide (OSP) of Bulkholderia vietnamiensis strain LMG 6988, and O-(2-acetamido-2-deoxy-β-D-mannopyranosyl)-(1 → 4)-O-α-D-galactopyranosyl-(1 → 4)-D-galactopyranose, a trisaccharide including a repeating unit of OSP of Acinetobactor baumannii serogroup O18, were synthesized by means of in-situ-activating glycosylation using 2-O-acetyl-3,4,6-tri-O-benzyl-D-glucopyranose (2ATBG) and a reagent mixture of p-nitrobenzenesulfonyl chloride, silver triflate, and 1,8-diazabicyclo[5.4.0]undec-7-ene, and related systems. New syntheses of 2ATBG, allyl 2,3,6-tri-O-benzyl-α-D-galactopyranoside, benzyl 2,3,6-tri-O-benzyl-α-D-galactopyranoside, and 2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-mannopyranose are described.
- Koto, Shinkiti,Shinoda, Yoshika,Hirooka, Motoko,Sekino, Akiko,Ishizumi, Sachiko,Koma, Mutsuko,Matuura, Chieko,Sakata, Naoko
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p. 1603 - 1615
(2007/10/03)
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- 1,3,4,6-Tetra-O-acetyl-2-chloroacetamido-2-deoxy-β-D-glucopyranose as a glycosyl donor in syntheses of oligosaccharides
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1,3,4,6-Tetra-O-acetyl-2-chloroacetamido-2-deoxy-β-D-glucopyranose was tested as a glycosyl donor for oligosaccharide synthesis via ferric chloride-catalyzed coupling reaction.Glycosyl acceptors tried (6 in all) were O-benzyl-protected D-galactosides having free OH groups at positions 3 and 4, respectively, and similarly protected glycosides of D-glucose and 2-acetamido-2-deoxy-D-glucose unsubstituted on O-4.Existing syntheses of all the acceptors were improved, in four instances by exploitation of Garegg and Hultberg's cyanoborohydride procedure for the conversion 4,6-O-benzylidene -> 6-O-benzyl .Good to excellent yields of β-linked disaccharides were obtained from the galactoside and glucoside acceptors, but with allyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside, stereoselectivity was lost (α:β-ratio 1:2).Allyl and benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosides gave, respectively, the allyl and benzyl β-glycosides of the donor as major products.A mechanism is proposed for this transglycosidation reaction.The N-chloroacetyl groups in the disaccharide products were readily converted into N-acetyl by reduction with zinc-acetic acid.
- Dasgupta, Falguni,Anderson, Laurens
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p. 239 - 255
(2007/10/02)
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