23701-87-3

Basic information

• Product Name: Methyl 6-azido-6-deoxy-alpha-D-glucopyranoside
• Synonyms: Methyl 6-azido-6-deoxy- a-D-glucopyranoside;METHYL 6-AZIDO-6-DEOXY-ALPHA-D-GLUCOPYRANOSIDE; 6-azido-6-deoxy-1-O-Methyl-α-D-glucopyranose
• CAS NO: 23701-87-3
• Molecular Formula: C₇H₁₃N₃O₅
• Molecular Weight: 219.2
• Product Categories: Sugars
• Mol File: 23701-87-3.mol
• Article Data: 19

Chemical Properties

• Melting Point: 102-104 °C
• Appearance: /
• Storage Temp.: -20°C Freezer
• Solubility: Dichloromethane; Ethyl Acetate; Methanol
• CAS DataBase Reference: Methyl 6-azido-6-deoxy-alpha-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 6-azido-6-deoxy-alpha-D-glucopyranoside(23701-87-3)
• EPA Substance Registry System: Methyl 6-azido-6-deoxy-alpha-D-glucopyranoside(23701-87-3)

Safety Data

• Hazardous Substances Data: 23701-87-3(Hazardous Substances Data)

Usage

Description

Methyl 6-azido-6-deoxy-alpha-D-glucopyranoside is a chemical compound that serves as an intermediate in the synthesis of various pharmaceuticals and is utilized in biological studies and therapeutic applications.

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 
• 14257-74-0 methyl 6-amino-6-deoxy-α-D-glucopyranoside 
• 6619-09-6 methyl 6-O-tosyl-α-D-glucopyranoside 
• 67-56-1 methanol 
• 1037515-73-3 1,3,6',3”-tetra-azido-kanamycin A 
• 23661-33-8 methyl 2,3,4-tri-O-acetyl-6-O-(p-tolylsulfonyl)-α-D-glucopyranoside 
• 104652-56-4 3-O-acetyl-1,2-O-isopropylidene-5-O-methylsulfonyl-6-O-(p-nitrobenzoyl)-D-glucofuranose 
• 104652-55-3 3-O-acetyl-1,2-O-isopropylidene-6-O-(p-nitrobenzoyl)-D-glucofuranose 
• 55263-80-4 1,2-O-isopropylidene-5-O-methylsulfonyl-D-glucofuranose 
• 104652-58-6 6-azido-6-deoxy-1,2-O-isopropylidene-β-L-idofuranose 
• 24807-96-3 3-O-acetyl-1,2-O-isopropylidene-α-D-glucofuranose 
• 300573-03-9 5,6-anhydro-1,2-O-isopropylidene-α-D-glucofuranose 

Downstream Products

• 5155-47-5 methyl 6-amino-6-deoxy-α-D-glucopyranoside 
• 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 
• 19139-89-0 (2R,3R,4S,5R,6S)-2-Azidomethyl-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran 
• 88713-76-2 6-azido-2,3,4-tri-O-benzyl-6-deoxy-D-glucono-1,5-lactone 
• 1582309-47-4 6-azido-6-deoxy-2,3,4-tri-O-benzyl-N-(prop-2-yn-1-yl)-D-gluconamide 
• 1338809-58-7 methyl 6-deoxy-6-((2S,6S)-6-methoxy-2-(hydroxymethyl)morpholin-4-yl)-α-D-glucopyranoside 
• 21893-05-0 methyl 2,3,4-tri-O-acetyl-6-azido-6-deoxy-β-L-idopyranoside 

Relevant articles and documents

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

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

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.