87326-88-3

Upstream product

• 17791-36-5 methyl 2,3-di-O-benzyl-α-D-glucopyranoside 
• 87326-90-7 methyl 4-O-acetyl-2,3-di-O-benzyl-6-deoxy-α-D-xylo-hex-5-enopyranoside 
• 87326-89-4 methyl 4-O-acetyl-2,3-di-O-benzyl-6-deoxy-6-iodo-α-D-glucopyranoside 
• 15354-29-7 methyl 4,6-O-isopropylidene-α-D-glucopyranoside 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 76491-08-2 methyl 2,3-di-O-benzyl-4,6-O-isopropylidene-α-D-glucopyranoside 
• 3162-96-7 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 
• 100-39-0 benzyl bromide 
• 54522-57-5 methyl-2,3-di-O-benzyl-6-O-(4-toluenesulfonyl)-α-D-glucopyranoside 
• 7177-79-9 methyl 2,3-O-dibenzyl-4,6-O-benzylidene-α-D-glucopyranoside 

Downstream Products

• 85716-44-5 methyl 2,3,4-tri-O-benzyl-α-d-xylo-hex-5-enopyranoside 
• 194800-88-9 (2S,3R,4S,5S)-3,4-Bis-benzyloxy-5-(2-iodo-benzyloxy)-2-methoxy-6-methylene-tetrahydro-pyran 
• 194800-96-9 5-((3S,4S,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-2-methylene-tetrahydro-pyran-3-yloxymethyl)-6-iodo-benzo[1,3]dioxole 
• 347897-51-2 ((2S,3S,4R,5R,6S)-4,5-Bis-benzyloxy-2-iodomethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-triethyl-silane 
• 681222-90-2 methyl 2,3-di-O-benzyl-4-O-allyl-6-deoxy-α-D-xylo-hex-5-enopyranoside 
• 309263-32-9 methyl 4-O-benzoyl-2,3-di-O-benzyl-6-deoxy-6-iodo-α-D-glucopyranoside 
• 56750-58-4 methyl 6-deoxy-2,3-bis-O-(phenylmethyl)-α-D-glucopyranoside 
• 250687-50-4 methyl 2,3-di-O-benzyl-4-O-crotonyl-6-deoxy-6-iodo-α-D-glucopyranoside 
• 681222-98-0 (2S,3R,4S,5S)-2-allyloxy-3,4-dibenzyloxy-5-methyloxycyclohexanone 
• 136458-74-7 2L-(2,4/3)-2-O-acetyl-3,4-di-O-benzyl-2,3,4-trihydroxy-5-cyclohexen-1-one 
• 127243-50-9 1D-(1,3/2,4)-3-O-acetyl-1,2-di-O-benzyl-5-cyclohexene-1,2,3,4-tetrol 
• 87326-90-7 methyl 4-O-acetyl-2,3-di-O-benzyl-6-deoxy-α-D-xylo-hex-5-enopyranoside 
• 122777-37-1 1D-(1,3/2,4)-3-O-acetyl-1,2-di-O-benzyl-4-O-tetrahydropyranyl-5-cyclohexene-1,2,3,4-tetrol 

Relevant academic research and scientific papers

Mapping the Relationship between Glycosyl Acceptor Reactivity and Glycosylation Stereoselectivity

The reactivity of both coupling partners—the glycosyl donor and acceptor—is decisive for the outcome of a glycosylation reaction, in terms of both yield and stereoselectivity. Where the reactivity of glycosyl donors is well understood and can be controlled through manipulation of the functional/protecting-group pattern, the reactivity of glycosyl acceptor alcohols is poorly understood. We here present an operationally simple system to gauge glycosyl acceptor reactivity, which employs two conformationally locked donors with stereoselectivity that critically depends on the reactivity of the nucleophile. A wide array of acceptors was screened and their structure–reactivity/stereoselectivity relationships established. By systematically varying the protecting groups, the reactivity of glycosyl acceptors can be adjusted to attain stereoselective cis-glucosylations.

Synthesis of MeON-neoglycosides of digoxigenin with 6-deoxy- and 2,6-dideoxy-D-glucose derivatives and their anticancer activity

Cardiac glycosides show anticancer activities and their deoxy-sugar chains are vital for their anticancer effects. In order to study the structure-activity relationship (SAR) of cardiac glycosides toward cancers and get more potent anticancer agents, a series of MeON-neoglycosides of digoxigenin was synthesized and evaluated. First, ten 6-deoxy- and 2,6-dideoxy-D-glucopyranosyl donors were synthesized starting from methyl α-D-glucopyranoside and 2-deoxy-D-glucose. Meanwhile, the digoxigenin was obtained by acidic hydrolysis of commercially available digoxin as glycosyl acceptor. Then, a 22-member MeON-neoglycoside library of digoxigenin was successfully synthesized by neoglycosylation method. Finally, the induction of Nur77 expression and its translocation from the nucleus to cytoplasm together with cytotoxicity of these MeON-neoglycosides were evaluated. The SAR analysis revealed that C3 glycosylation is required for their induction of Nur77 expression. Moreover, some MeON-neoglycosides (2b and 8b) could significant induce the expression of Nur77 and its translocation from the nucleus to cytoplasm. However, these compounds showed no inhibitory effects on the proliferation of cancer cells, suggesting that they may not induce apoptosis of NIH-H460 cancer cells and their underlying potential and application toward cancer cells deserves future study.

Selective S-deacetylation inspired by native chemical ligation: practical syntheses of glycosyl thiols and drug mercapto-analogues

Glycosyl thiols are useful building blocks for the construction of compounds of biological and synthetic importance. Herein, we report a practical synthetic approach toward the efficient synthesis of glycosyl thiols via chemo- and regioselective S-deacetylation inspired by native chemical ligation. This strategy allows the large scale synthesis of glycosyl thiols by simple purification steps without column chromatography. In addition, deacetylation reagents (DTT) could also be recovered and regenerated by a simple process. Thiol containing taxol and artemisinin analogues were successfully prepared based on this methodology. Finally, auranofin, a glucose-based oral drug used to treat rheumatoid arthritis, was synthesized in concise steps and overall high yields.

Stereoselective synthesis of α-linked 2-deoxy glycosides enabled by visible-light-mediated reductive deiodination

2-Deoxy sugars and their derivatives occur abundantly in many pharmaceutically important natural products. However, the construction of specific 2-deoxy-glycosidic bonds remains as a challenge. Herein, we report an efficient way to prepare 2-deoxy-a-glycosides by glycosylation of 2-iodo-glycosyl acetate and subsequent visible-light-mediated tin-free reductive deiodination. We have successfully applied the postglycosylational-deiodination strategy in the synthesis of more than 30 mono-, di-, tri-, tetra- and pentadeoxysaccharides with excellent stereoselectivity and efficiency. This method has also been applied to the synthesis of a 2-deoxy-tetrasac-charide containing four a-linkages.

Synthesis of the AB subunit of angelmicin B through a tandem alkoxy radical fragmentation-etherification sequence

(Chemical Equation Presented) The synthesis of the tricyclic enone 2, corresponding to the AB subunit of the novel tyrosine kinase inhibitor angelmicin B, is described. The strategy centers on an intramolecular Diels-Alder (IMDA) reaction on triene 4 to p

A flexible stereospecific synthesis of polyhydroxylated pyrrolizidines from commercially available pyranosides

Nitrogen-containing sugar analogues, known as azasugars or iminosugars, such as polyhydroxylated piperdines, pyrrolidines, pyrrolizidines, and indolizidines, have the potential to become important therapeutic agents due to their ability to inhibit glycosi

Synthesis of the BCD-ring of ciguatoxin 1B using an acetylene cobalt complex and vinylsilane strategy

Synthesis of the tricyclic BCD-ring segment with high stereoselectivity has been achieved starting from a sugar derivative directed toward the synthesis of the left part of ciguatoxin 1B. The central reactions in the synthesis are (i) ether ring formation mediated by an acetylene cobalt complex, (ii) decomplexation of the endo-acetylene cobalt complex to the vinylsilane, and (iii) ring-opening reaction of the epoxysilane into the allylic alcohol.

Highly stereoselective 1,4-conjugate addition of organocopper reagents to methyl α-D-glucopyranoside derivatives tethering an unsaturated ester moiety at C-4 or C-6

(formula presented) The 1,4-conjugate additions of a variety of organocopper reagents to some 4-O-crotonyl derivatives of methyl α-D-glucopyranoside proceeded with a high level of diastereochemical induction to provide the adducts carrying a β-substituted

Total Synthesis of Hygromycin A

The first complete synthesis of antibiotic hygromycin A is reported; coupling of the protected sugar moiety (2) and the aminocyclitol (3) derived from D-glucose as the optically active form, followed by deprotection, gives the product (1) which was identi