23701-87-3

Usage

Uses

Used in Pharmaceutical Synthesis:
Methyl 6-azido-6-deoxy-alpha-D-glucopyranoside is used as an intermediate in the synthesis of Ranimustine (R120030), a nitrosourea alkylating agent. Methyl 6-azido-6-deoxy-alpha-D-glucopyranoside is approved in Japan for the treatment of chronic myelogenous leukemia and polycythemia vera, making it a crucial component in the development of these medications.
Used in Biological Studies:
Methyl 6-azido-6-deoxy-alpha-D-glucopyranoside is employed in the study of the synthesis of anti-EGFR (epidermal growth factor receptor) antibody-drug conjugates. It plays a significant role in the development of targeted therapies for various types of cancer, as it helps in the creation of molecules that can specifically bind to and inhibit the growth of cancer cells.
Used in Therapeutic Applications:
Methyl 6-azido-6-deoxy-alpha-D-glucopyranoside is also used in the therapeutic use and biological study of BCMA (B-Cell Maturation Antigen) antigen binding proteins. These proteins are involved in the regulation of B-cell differentiation and are potential targets for the treatment of certain B-cell malignancies, such as multiple myeloma and certain types of leukemia.

InChI:InChI=1/C7H13N3O5/c1-14-7-6(13)5(12)4(11)3(15-7)2-9-10-8/h3-7,11-13H,2H2,1H3/t3-,4-,5+,6-,7+/m1/s1

Upstream product

• 21893-05-0 methyl 2,3,4-tri-O-acetyl-6-azido-6-deoxy-β-L-idopyranoside 
• 7465-44-3 methyl 6-bromo-6-deoxy-α-D-glucopyranoside 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 4144-87-0 methyl 6-chloro-6-deoxy-α-D-glucopyranoside 
• 14257-74-0 methyl 6-amino-6-deoxy-α-D-glucopyranoside 
• 6619-09-6 methyl 6-O-tosyl-α-D-glucopyranoside 
• 300573-03-9 5,6-anhydro-1,2-O-isopropylidene-α-D-glucofuranose 
• 24807-96-3 3-O-acetyl-1,2-O-isopropylidene-α-D-glucofuranose 
• 104652-58-6 6-azido-6-deoxy-1,2-O-isopropylidene-β-L-idofuranose 
• 55263-80-4 1,2-O-isopropylidene-5-O-methylsulfonyl-D-glucofuranose 
• 104652-55-3 3-O-acetyl-1,2-O-isopropylidene-6-O-(p-nitrobenzoyl)-D-glucofuranose 
• 104652-56-4 3-O-acetyl-1,2-O-isopropylidene-5-O-methylsulfonyl-6-O-(p-nitrobenzoyl)-D-glucofuranose 
• 23661-33-8 methyl 2,3,4-tri-O-acetyl-6-O-(p-tolylsulfonyl)-α-D-glucopyranoside 
• 67-56-1 methanol 

Downstream Products

• 21893-05-0 methyl 2,3,4-tri-O-acetyl-6-azido-6-deoxy-β-L-idopyranoside 
• 20847-05-6 6-Azido-6-desoxy-D-glucopyranose 
• 1326710-36-4 C₁₄H₁₅Cl₂NO₅ 
• 1326710-42-2 C₁₅H₁₆F₃NO₅ 
• 1326710-32-0 C₁₄H₁₇NO₅ 
• 1326710-38-6 C₁₄H₁₇NO₆ 
• 1326710-40-0 C₂₀H₂₁NO₅ 
• 1582309-47-4 6-azido-6-deoxy-2,3,4-tri-O-benzyl-N-(prop-2-yn-1-yl)-D-gluconamide 
• 88713-76-2 6-azido-2,3,4-tri-O-benzyl-6-deoxy-D-glucono-1,5-lactone 
• 19139-89-0 (2R,3R,4S,5R,6S)-2-Azidomethyl-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran 
• 1338809-58-7 methyl 6-deoxy-6-((2S,6S)-6-methoxy-2-(hydroxymethyl)morpholin-4-yl)-α-D-glucopyranoside 
• 5155-47-5 methyl 6-amino-6-deoxy-α-D-glucopyranoside 

Relevant academic research and scientific papers

Diesterification of 3-[(β-cyclodextrinyl)succinamido]propane-1,2-diol catalysed by lipase: Diastereoselectivity or tridimensional substrate specificity?

The transesterification of 3-[(β-cyclodextrinyl)succinamido]propane-1,2-diol with fatty esters catalyzed by immobilized lipase from Mucor miehei occurred with very different conversions of the two diastereoisomers [(R)- or (S)-amidopropanediol]. The highe

Design, physico-chemical characterization andin vitrobiological activity of organogold(iii) glycoconjugates

To develop new metal-based glycoconjugates as potential anticancer agents, four organometallic gold(iii)-dithiocarbamato glycoconjugates of the type [AuIII(2-Bnpy)(SSC-Inp-GlcN)](PF6) (2-Bnpy: 2-benzylpyridine; Inp: isonipecotic moie

An alternative and facile synthetic approach for the precursors of 3- and 6-aminosugar donors and study of one-pot glycosyltrasferation

3- and 6-aminosugars are common motifs in bioactive compounds playing pivotal roles in the bioactivity of the core molecules to which they are attached. However, de novo synthesis of 3- and 6-aminosugars and their corresponding glycosyl donors can be time

An innovative and efficient route to the synthesis of metal-based glycoconjugates: proof-of-concept and potential applications

With a view to developing more efficient strategies to the functionalization of metallodrugs with carbohydrates, we here report on an innovative and efficient synthetic route to generate gold(iii) glycoconjugates in high yields and purity. The method is based on the initial synthesis of the zinc(ii)-dithiocarbamato intermediate [ZnII(SSC-Inp-GlcN)2] (Inp = isonipecotic moiety; GlcN = amino-glucose) followed by the transfer of the glucoseisonipecoticdithiocarbamato ligand to the gold(iii) center via transmetallation reaction between the zinc(ii) intermediate and K[AuIIIBr4] in 1?:?2 stoichiometric ratio, yielding the corresponding glucose-functionalized gold(iii)-dithiocarbamato derivative [AuIIIBr2(SSC-Inp-GlcN)]. No protection/deprotection of the amino-glucose scaffold and no chromatographic purification were needed. The synthetic protocol was optimized for glucose precursors bearing the amino function at either the C2 or the C6 position, and works in the case of both α and β anomers. The application of the synthetic strategy was also successfully extended to other metal ions of biomedical interest, such as gold(i) and platinum(ii), to obtain [AuI(SSC-Inp-GlcN)(PPh3)] and [PtII(SSC-Inp-GlcN)2], respectively. All compounds were fully characterized by elemental analysis, mid- and far-IR, mono- and multidimensional NMR spectroscopy, and, where possible, X-ray crystallography. Results and potential applications are here discussed.

Facile and Versatile Chemoenzymatic Synthesis of Enterobactin Analogues and Applications in Bacterial Detection

Siderophores, such as enterobactin (Ent), are small molecules that can be selectively imported into bacteria along with iron by cognate transporters. Siderophore conjugates are thus a promising strategy for delivering functional reagents into bacteria. In this work, we present an easy-to-perform, one-pot chemoenzymatic synthesis of functionalized monoglucosylated enterobactin (MGE). When functionalized MGE is conjugated to a rhodamine fluorophore, which affords RhB-Glc-Ent, it can selectively label Gram-negative bacteria that utilize Ent, including some E. coli strains and P. aeruginosa. V. cholerae, a bacterium that utilizes linearized Ent, can also be weakly targeted. Moreover, the targeting is effective under iron-limiting but not iron-rich conditions. Our results suggest that the RhB-Glc-Ent probe is sensitive not only to the bacterial strain but also to the iron condition in the environment.

Linear poly(amide triazole)s derived from d -glucose

The click reaction between azides and alkynes is been increasingly employed in the preparation of polymers. In this article, we describe the synthesis and click polyaddition reaction of a new A-B-type amide monomer - prepared from d-glucose as renewable r

Quantifying the electronic effects of carbohydrate hydroxy groups by using aminosugar models

Methyl amino-deoxy-glycosides with α- and β-gluco, α-galacto, or α-manno stereochemistry with the amino functionality in each of the four possible non-anomeric positions have been synthesized and their pKa values determined by titration. These

Synthesis and glycosidase inhibitory profiles of functionalised morpholines and oxazepanes

In this work libraries of morpholines and oxazepanes have been prepared via the reductive amination reaction between dialdehydes, derived from carbohydrates, and a range of amines. In this way, functionalised morpholines and oxazepanes have been prepared

Synthesis and antibacterial activity of aminodeoxyglucose derivatives against Listeria innocua and Salmonella typhimurium

In this study aminodeoxyglucose derivatives were synthesized and evaluated for their antibacterial activity against two food bacteria, Listeria innocua and Salmonella typhimurium. 6-Amino-6-deoxy-α-Dmethylglucopyranose (GSA-6), 3-amino-3-deoxy-D-glucopyranoside (GSA-3), and β-D-glucopyranosylamine (GSA-1) were synthesized and concurrently tested with commercially available D-glucosamine (GSA-2) for antibacterial activity. Results obtained from this study showed a pronounced antagonist effect due to the position of amino groups of aminoglucose derivatives on the antibacterial activity. GSA-3 was the most active compound. At a concentration of 2 × 10 -4 mol mL -1, it delayed the growth of both bacteria with percentages of inhibition of 29 and 15% for L. innocua and S. typhimurium, respectively. At the same concentration the percentages of inhibition for other aminodeoxyglucoses varied between 5 and 18% and between 2 and 11% for L. innocua and S. typhimurium, respectively. All compounds were characterized by FTIR, 1H NMR, and 13C NMR spectroscopy.

METHODS, COMPOUNDS, COMPOSITIONS AND VEHICLES FOR DELIVERING 3-AMINO-1-PROPANESULFONIC ACID

The invention relates to methods, compounds, compositions and vehicles for delivering 3-amino-1-propanesulfonic acid (3APS) in a subject, preferably a human subject. The invention encompasses compounds that will yield or generate 3APS, either in vitro or in vivo. Preferred compounds include amino acid prodrugs of 3APS for use, including but not limited to, the prevention and treatment of Alzheimer's disease.