METHYL 6-AMINO-6-DEOXY-GALACTOPYRANOSIDE

Base Information

• Chemical Name: METHYL 6-AMINO-6-DEOXY-GALACTOPYRANOSIDE
• CAS No.: 5155-47-5
• Molecular Formula: C₇H₁₅NO₅
• Molecular Weight: 193.2
• Hs Code.: 2922390090
• Mol file: 5155-47-5.mol

Synonyms:Glucopyranoside,methyl 6-amino-6-deoxy- (6CI,7CI);Glucopyranoside, methyl 6-amino-6-deoxy-, α-D- (8CI);Methyl 6-amino-6-deoxy-α-D-glucopyranoside;1-O-Methyl-6-deoxy-6-amino-α-D-glucopyranose;(3R,5S,6R)-2-(Aminomethyl)-6-methoxy-tetrahydropyran-3,4,5-triol;

Chemical Property of METHYL 6-AMINO-6-DEOXY-GALACTOPYRANOSIDE

Chemical Property:

• Vapor Pressure: 5.81E-07mmHg at 25°C
• Refractive Index: 1.55
• Boiling Point: 369.5 °C at 760 mmHg
• PKA: 12.94±0.70(Predicted)
• Flash Point: 177.2 °C
• PSA: 105.17000
• Density: 1.39 g/cm³
• LogP: -1.90060
• Storage Temp.: 2-8°C

Purity/Quality:

98%min ^*data from raw suppliers

Methyl 6-amino-6-deoxy-a-D-glucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: Methyl 6-?Amino-?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-AMINO-6-DEOXY-GALACTOPYRANOSIDE

There total 18 articles about METHYL 6-AMINO-6-DEOXY-GALACTOPYRANOSIDE 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-azido-6-deoxy-α-D-glucopyranoside (23701-87-3) → methyl 6-amino-6-deoxy-α-D-glucopyranoside (5155-47-5,68396-86-1,68422-61-7,79695-15-1,83334-22-9,83377-36-0,104714-43-4,104714-44-5,496811-81-5)

Guidance literature:

With hydrogen; In methanol; for 18h;

DOI:10.1016/j.bmc.2011.07.019

Reference yield: 38.0%

C63H67NO9 (1332641-39-0) → methyl 6-[5a-carba-α-D-xylo-hex-5(5a)-enopyranosylamino]-6-deoxy-α-D-glucopyranoside (1333121-74-6) + methyl 6-amino-6-deoxy-α-D-glucopyranoside (5155-47-5,68396-86-1,68422-61-7,79695-15-1,83334-22-9,83377-36-0,104714-43-4,104714-44-5,496811-81-5)

Guidance literature:

With ammonia; sodium; In tetrahydrofuran; at -78 ℃; for 0.333333h; Inert atmosphere;

DOI:10.1016/j.bmcl.2011.07.046

Reference yield:

methyl 2,3,4-tri-O-acetyl-6-azido-6-deoxy-β-L-idopyranoside (21893-05-0) → methyl 6-amino-6-deoxy-α-D-glucopyranoside (5155-47-5,68396-86-1,68422-61-7,79695-15-1,83334-22-9,83377-36-0,104714-43-4,104714-44-5,496811-81-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / barium hydroxide octahydrate / methanol / 0.17 h / Ambient temperature

2: 79 percent / H₂ / Pd-black / H₂O / 1 h

With barium hydroxide octahydrate; hydrogen; palladium; In methanol; water;

DOI:10.1246/bcsj.59.1397

upstream raw materials:

methyl 6-O-tosyl-α-D-glucopyranoside

methyl-alpha-D-glucopyranoside

methyl 6-azido-6-deoxy-α-D-glucopyranoside

methanol

Downstream raw materials:

Ranimustine

methyl 6-(4-bromomethyl-3-nitrobenzoylamino)-6-deoxy-α-D-glucopyranoside

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

1-amino-1-deoxy-N-(methyl 6-amino-6-deoxy-α-D-glucopyranosid-6-yl)-5,6-oxomethylidenenojirimycin

Refernces

• 1、 Sangwan, Rekha,Dubey, Atul,Tiwari, Ashwani,Mandal, Pintu Kumar. "The strategic use of: Para-quinone methides to access synthetically challenging and chemoselective α,α-diarylmethyl N-glycosides from unprotected carbohydrate amines". supporting information. p. 1343 - 1348. Retrieved 2020/03/03.
• 2、 Sommer, Roman,Hauck, Dirk,Varrot, Annabelle,Wagner, Stefanie,Audfray, Aymeric,Prestel, Andreas,M?ller, Heiko M.,Imberty, Anne,Titz, Alexander. "Cinnamide Derivatives of d-Mannose as Inhibitors of the Bacterial Virulence Factor LecB from Pseudomonas aeruginosa". . p. 756 - 767. Retrieved 2016/07/06.