Synthesis of iminoalditol analogues of galactofuranosides and their activities against glycosidases

Sandbhor, Mahendra; Bhasin, Milan; Williams, Dean T.; Hsieh, Margaret; Wu, Shih‐Hsiung; Zou, Wei

doi:10.1016/j.carres.2008.07.013

Cited by 9 publications

(6 citation statements)

References 41 publications

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“…The displacement of the trifluoromethanesulfonate by sodium azide in dimethylformamide gave a good yield of methyl 4-azido-2,3,6-tri-O-benzoyl-4-deoxy-α-D-glucopyranoside in syrup form. 24 The debenzoylation of methyl 2,3,6-tri-O-benzoyl-4-azido-4-deoxy-α-D-glucopy-ranoside with sodium methoxide resulted in crystalline methyl 4-azido-4-deoxy-α-D-glucopyranoside, which was subsequently peracetylated to obtain a syrupy 1,2,3,6-tetra-O-acetyl-4-azido-4-deoxy-α-D-glucose (4a). 1,2,3,4-Tetraacetyl-6-O-p-tolylsulfonyl-D-glucopyranose was prepared from D-glucose as previously described.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Glucose Positions Affect the Phloem Mobility of Glucose–Fipronil Conjugates

Lei

Wang

Mao

et al. 2014

J. Agric. Food Chem.

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In our previous work, a glucose-fipronil (GTF) conjugate at the C-1 position was synthesized via click chemistry and a glucose moiety converted a non-phloem-mobile insecticide fipronil into a moderately phloem-mobile insecticide. In the present paper, fipronil was introduced into the C-2, C-3, C-4, and C-6 positions of glucose via click chemistry to obtain four new conjugates and to evaluate the effects of the different glucose isomers on phloem mobility. The phloem mobility of the four new synthetic conjugates and GTF was tested using the Ricinus seedling system. The results confirmed that conjugation of glucose at different positions has a significant influence on the phloem mobility of GTF conjugates.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Glucose Positions Affect the Phloem Mobility of Glucose–Fipronil Conjugates

Lei

Wang

Mao

et al. 2014

J. Agric. Food Chem.

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“…130,131 The key step in their approach is the intramolecular S N of a 2-amino-2-deoxy-heptono-1,4-lactone carrying a leaving group at position 5 (e.g., 112). The cyclization is promoted by the opening of the lactone with an alcohol, to give 2,5-imino-aldonates such as 113 or with an amine to give 2,5-imino-aldonamides such as 114 (Scheme 87 Another approach to imino-galactofuranose C-glycosides was recently described by Zou et al 132 The synthesis starts with an a-1-C-allyl D-galactopyranose derivative carrying an azido group at C-4; oxidation of the allyl group to a 2-oxopropyl group leads to a system that can undergo ring opening to an unsaturated ketone by b-elimination under basic conditions. Hydrogenolysis of the azido group followed by treatment of the resulting amine with LiOH promotes this b-elimination and subsequent cyclization by conjugate addition to a pyrrolidine as a mixture of C-1 isomers (Scheme 88; see also Section 2.…”

Section: Other Cyclizations By Internal S Nmentioning

confidence: 98%

Tactics and strategies for the synthesis of iminosugar C-glycosides: a review

Compain

Chagnault

Martin

2009

Tetrahedron: Asymmetry

158

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“…1- O -Methyl sugars require strongly acidic conditions for effective electrophilic C -glycosylation with C -nucleophiles through the oxocarbenium ion similarly to the C -glycosylation of glycosyl halides (Scheme a). − , Thus, allylation of a range of methyl glycosides with allyltrimethylsilane under the promotion of BF 3 ·OEt 2 or TMSOTf provided α- C -allyl glycosides 678 – 683 as the sole or predominant products in moderate to good yields (58–85%) (Scheme ). ,− …”

Section: C-glycosylation With 1-o-methyl Sugarsmentioning

confidence: 99%

Recent Advances in the Chemical Synthesis of C-Glycosides

2017

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Advances in the chemical synthesis of C-pyranosides/furanosides are summarized, covering the literature from 2000 to 2016. The majority of the methods take advantage of the construction of the glycosidic C-C bond. These C-glycosylation methods are categorized herein in terms of the glycosyl donor precursors, which are commonly used in O-glycoside synthesis and are easily accessible to nonspecialists. They include glycosyl halides, glycals, sugar acetates, sugar lactols, sugar lactones, 1,2-anhydro sugars, thioglycosides/sulfoxides/sulfones, selenoglycosides/telluroglycosides, methyl glycosides, and glycosyl imidates/phosphates. Mechanistically, C-glycosylation reactions can involve glycosyl electrophilic/cationic species, anionic species, radical species, or transition-metal complexes, which are discussed as subcategories under each type of sugar precursor. Moreover, intramolecular rearrangements, such as the Claisen rearrangement, Ramberg-Bäcklund rearrangement, and 1,2-Wittig rearrangement, which usually involve concerted pathways, constitute another category of C-glycosylations. An alternative to the C-glycosylations is the formation of pyranoside/furanoside rings after construction of the predetermined glycosidic C-C bonds, which might involve cyclization of acyclic precursors or D-A cycloadditions. Throughout, the stereoselectivity in the formation of the resultant C-glycosidic linkages is highlighted.

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Synthesis of iminoalditol analogues of galactofuranosides and their activities against glycosidases

Cited by 9 publications

References 41 publications

Glucose Positions Affect the Phloem Mobility of Glucose–Fipronil Conjugates

Glucose Positions Affect the Phloem Mobility of Glucose–Fipronil Conjugates

Tactics and strategies for the synthesis of iminosugar C-glycosides: a review

Recent Advances in the Chemical Synthesis of C-Glycosides

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