Methyl 6-azido-6-deoxy-alpha-D-glucopyranoside

Base Information

• Chemical Name: Methyl 6-azido-6-deoxy-alpha-D-glucopyranoside
• CAS No.: 23701-87-3
• Molecular Formula: C7H13N3O5
• Molecular Weight: 219.197
• Hs Code.: 2932999099
• Mol file: 23701-87-3.mol

Synonyms:Glucopyranoside,methyl 6-azido-6-deoxy-, a-D- (6CI,8CI);

Chemical Property of Methyl 6-azido-6-deoxy-alpha-D-glucopyranoside

Chemical Property:

• Melting Point: 102-104 °C
• PSA: 128.90000
• LogP: -1.79654
• Storage Temp.: -20°C Freezer
• Solubility.: Dichloromethane; Ethyl Acetate; Methanol

Purity/Quality:

99% ^*data from raw suppliers

Methyl6-Azido-6-deoxy-α-D-glucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Methyl 6-Azido-6-deoxy-α-D-glucopyranoside is an intermediate in synthesizing Ranimustine (R120030), a nitrosourea alkylating agent approved in Japan for the treatment of chronic myelogenous leukemia and polycythemia vera. It can be used in biological study of synthesis of anti-EGFR antibody-drug conjugates. It can also be used in therapeutic use and biological study of BCMA (B-Cell Maturation Antigen) antigen binding proteins.

Technology Process of Methyl 6-azido-6-deoxy-alpha-D-glucopyranoside

There total 15 articles about Methyl 6-azido-6-deoxy-alpha-D-glucopyranoside which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

methyl 6-amino-6-deoxy-α-D-glucopyranoside (14257-74-0) → methyl 6-azido-6-deoxy-α-D-glucopyranoside (23701-87-3)

Guidance literature:

With triflic azide; sodium hydrogencarbonate; copper(II) sulfate; In methanol; toluene; at 20 ℃; for 14h;

DOI:10.1016/j.tetlet.2006.01.157

Reference yield: 99.0%

methyl 2,3,4-tri-O-acetyl-6-azido-6-deoxy-β-L-idopyranoside (21893-05-0) → methyl 6-azido-6-deoxy-α-D-glucopyranoside (23701-87-3)

Guidance literature:

With methanol; sodium methylate; at 20 ℃; for 0.0333333h; sonication;

DOI:10.1021/jo060374w

Reference yield: 99.0%

methyl 6-chloro-6-deoxy-α-D-glucopyranoside (4144-87-0) → methyl 6-azido-6-deoxy-α-D-glucopyranoside (23701-87-3)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; for 48h; Heating;

DOI:10.1016/S0008-6215(96)00336-9

upstream raw materials:

methyl 2,3,4-tri-O-acetyl-6-azido-6-deoxy-β-L-idopyranoside

methyl 6-bromo-6-deoxy-α-D-glucopyranoside

methyl-alpha-D-glucopyranoside

methyl 6-chloro-6-deoxy-α-D-glucopyranoside

Downstream raw materials:

methyl 6-amino-6-deoxy-α-D-glucopyranoside

methyl 2,3,4-tri-O-acetyl-6-azido-6-deoxy-β-L-idopyranoside

6-Azido-6-desoxy-D-glucopyranose

methyl 6-deoxy-6-((2S,6S)-6-methoxy-2-(hydroxymethyl)morpholin-4-yl)-α-D-glucopyranoside

Refernces

• 1、 Pettenuzzo, Andrea,Vezzù, Keti,Di Paolo, Maria Luisa,Fotopoulou, Eirini,Marchiò, Luciano,Via, Lisa Dalla,Ronconi, Luca. "Design, physico-chemical characterization andin vitrobiological activity of organogold(iii) glycoconjugates". supporting information. p. 8963 - 8979. Retrieved 2021/07/02.
• 2、 Pettenuzzo, Andrea,Montagner, Diego,McArdle, Patrick,Ronconi, Luca. "An innovative and efficient route to the synthesis of metal-based glycoconjugates: proof-of-concept and potential applications". supporting information. p. 10721 - 10736. Retrieved 2018/08/17.