250127-77-6

Upstream product

• 63734-12-3 methyl 6-O-(tert-butyldimethylsilyl)-α-D-glucopyranoside 
• 166592-73-0 methyl 2,3,4-tri-O-benzyl-6-O-(tert-butyldimethylsilyl)-α-D-glucopyranoside 
• 2595-06-4 methyl 2,3,4-tri-O-benzyl-6-O-trityl-α-D-glucopyranoside 
• 18311-26-7 methyl 6-O-trityl-α-D-glucopyranoside 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 53008-65-4 methyl 2,3,4-tri-O-benzyl-D-glucopyranoside 
• 106-96-7 propargyl bromide 

Downstream Products

• 53008-65-4 methyl 2,3,4-tri-O-benzyl-D-glucopyranoside 
• 167777-17-5 methyl 6-O-allyl-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 1161826-43-2 6-[4-(methyl 2,3,4-tri-O-benzyl-α-D-glucopyranosid-6-yloxy)-methyl-1H-1,2,3-triazol-1-yl]hexyl 3β-hydroxyolean-12-en-28-oate 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 604-70-6 Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-methoxy-tetrahydro-pyran-4-yl ester 
• 1425503-79-2 C₂₂H₂₇N₃O₉ 
• 1338450-97-7 1,6-di-O-(methyl-2,3,4-tri-O-benzyl-6-yl-α-D-glucopyranoside)-2,4-hexadiyne 
• 1335214-86-2 methyl 3-hydroxy-5-(4-(4-((((2R,3R,4S,5R,6S)-3,4,5-tris(benzyloxy)-6-methoxytetrahydro-2H-pyran-2-yl)methoxy)methyl)-1H-1,2,3-triazol-1-yl)butoxy)benzoate 
• 1335214-85-1 methyl 2-hydroxy-5-(4-(4-((((2R,3R,4S,5R,6S)-3,4,5-tris(benzyloxy)-6-methoxytetrahydro-2H-pyran-2-yl)methoxy)methyl)-1H-1,2,3-triazol-1-yl)butoxy)benzoate 
• 1335214-84-0 methyl 3-(4-(4-((((2R,3R,4S,5R,6S)-3,4,5-tris(benzyloxy)-6-methoxytetrahydro-2H-pyran-2-yl)methoxy)methyl)-1H-1,2,3-triazol-1-yl)butoxy)benzoate 
• 1335214-83-9 methyl 3-hydroxy-5-(3-(4-((((2R,3R,4S,5R,6S)-3,4,5-tris(benzyloxy)-6-methoxytetrahydro-2H-pyran-2-yl)methoxy)methyl)-1H-1,2,3-triazol-1-yl)propoxy)benzoate 
• 1335214-82-8 methyl 2-hydroxy-5-(3-(4-((((2R,3R,4S,5R,6S)-3,4,5-tris(benzyloxy)-6-methoxytetrahydro-2H-pyran-2-yl)methoxy)methyl)-1H-1,2,3-triazol-1-yl)propoxy)benzoate 
• 1335214-81-7 methyl 3-(3-(4-((((2R,3R,4S,5R,6S)-3,4,5-tris(benzyloxy)-6-methoxytetrahydro-2H-pyran-2-yl)methoxy)methyl)-1H-1,2,3-triazol-1-yl)propoxy)benzoate 
• 1335215-06-9 3-hydroxy-5-(5-(4-((((2R,3R,4S,5R,6S)-3,4,5-tris(benzyloxy)-6-methoxytetrahydro-2H-pyran-2-yl)methoxy)methyl)-1H-1,2,3-triazol-1-yl)pentyloxy)benzoic acid 

Relevant academic research and scientific papers

Addressing the biochemical foundations of a glucose-based "trojan horse"-strategy to boron neutron capture therapy: From chemical synthesis to in vitro assessment

Boron neutron capture therapy (BNCT) for cancer is on the rise worldwide due to recent developments of in-hospital neutron accelerators which are expected to revolutionize patient treatments. There is an urgent need for improved boron delivery agents, and herein we have focused on studying the biochemical foundations upon which a successful GLUT1-targeting strategy to BNCT could be based. By combining synthesis and molecular modeling with affinity and cytotoxicity studies, we unravel the mechanisms behind the considerable potential of appropriately designed glucoconjugates as boron delivery agents for BNCT. In addition to addressing the biochemical premises of the approach in detail, we report on a hit glucoconjugate which displays good cytocompatibility, aqueous solubility, high transporter affinity, and, crucially, an exceptional boron delivery capacity in the in vitro assessment thereby pointing toward the significant potential embedded in this approach.

New class of alkynyl glycoside analogues as tyrosinase inhibitors

A new series of alkynyl glycoside analogues were designed and synthesized from cheap and a commercially available sugar by introduction of various alkynyl and alkyl groups at C-1 and C-6 positions of the sugar ring. The inhibitory abilities of alkynyl gly

Co2(CO)6-propargyl cation mediates glycosylation reaction by using thioglycoside

We discovered that the cobalt-propargyl cation can mediate the glycosylation reaction by activating the thioglycoside donor. The glyco-oxacarbenium cation was formed by transferring the thio-aglycone to the cobalt-propargyl cation that was generated from the cobalt-propargylated acceptor in situ via the activating with Lewis acid. The reactivity of the donor (Armed or dis-armed) and the amount of the Lewis acid control the releasing rate of the cobalt-propargyl group.

A new method testing the orthogonality of different protecting groups

A new test was elaborated to identify a new set of orthogonal protecting groups. With the developed method eight different protecting groups were tested under various deprotection conditions and the complex reaction mixtures were analysed by HPLC. The dev

Regioselective facile synthesis of novel isoxazole-linked glycoconjugates

A concise and efficacious protocol for the regioselective synthesis of novel 3,5-disubstituted isoxazole-linked glycoconjugates (4, 7 and 9) via a 1,3-dipolar cycloaddition reaction between in situ generated glycosyl-β-nitrile oxide (derived from glycosyl

Intramolecular glycosidation by click reaction mediated spacer generation followed by spacer cleavage

2-O-Propargyl-substituted glycosyl donors and O-(2-azidobenzyl)-substituted acceptors having a vicinal hydroxy group readily underwent the click reaction. Intramolecular glycosidation with N-iodosuccinimide/trifluoromethansulfonic acid as the activating system afforded β-(1-3)- and α-(1-2)-linked disaccharides as part of 14-membered macrocycles. Descriptors for these reactions are proposed that consider the donor and acceptor attachment sites and the stereochemistry of the functional groups. Investigation of the influence of 2-O-linked 1-aryl-1,2,3-triazol-4-ylmethyl groups, as contained in the spacer, on the anomeric selectivity exhibited no anchimeric assistance. In addition, it was shown that the spacer group can be readily cleaved under Birch reduction conditions. The 1,2,3-triazole-forming click reaction was employed to generate glycosyl donor-spacer-acceptor constructs. Upon glycosidation, 14-membered macrocycles were obtained with high anomeric selectivity. Spacer cleavage was performed under Birch reduction conditions. Copyright

Synthesis of glucoconjugates of oleanolic acid as inhibitors of glycogen phosphorylase

Synthesis and biological evaluation of glucoconjugates of oleanolic acid, linked by either a triazole moiety or an ester function, as novel inhibitors of glycogen phosphorylase have been described. Several triterpene-glycoside conjugates exhibited moderate-to-good inhibitory activity against rabbit muscle GPa. Compound 12 showed the best inhibition with an IC50 value of 1.14 μM. Structure-activity relationship (SAR) analysis of these inhibitors is also discussed. Possible binding modes of compound 12 were explored by molecular docking simulations.

Study of metal and acid catalysed deprotection of propargyl ethers of alcohols via their allenyl ethers

A new method for the deprotection of prop-2-ynyl ethers 1b-9b is described. Isomerisation of 1b-9b to O-allenyl ethers 1d-9d and deprotection by reaction with Hg(OCOCF3)2, aq.HCl, aq.CF3CO2H and best by use of a catalytic amount of OsO4 is described to obtain the alcohols 1a-9a in good yield. Application of this method for the deprotection of prop-2-enyl ethers 7c,8c,10c-13c via their corresponding prop-1-enyl ethers 7e,8e,10e-13e to obtain the corresponding alcohols 7a,8a,10a-13a is also described.