(2R,3S,4S,5R,6R)-2-(azidomethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol

Base Information

• Chemical Name: (2R,3S,4S,5R,6R)-2-(azidomethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol
• CAS No.: 87586-16-1
• Molecular Formula: C₇H₁₃N₃O₅
• Molecular Weight: 219.197
• Mol file: 87586-16-1.mol

Synonyms:(2R,3S,4S,5R,6R)-2-(azidomethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol

Chemical Property of (2R,3S,4S,5R,6R)-2-(azidomethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4S,5R,6R)-2-(azidomethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol

There total 1 articles about (2R,3S,4S,5R,6R)-2-(azidomethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol 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: 34.0%

methanol (67-56-1) + 1,3,6',3”-tetra-azido-kanamycin A (1037515-73-3) → methyl-3-azido-3-deoxy-α-D-glucopyranoside (5152-11-4) + methyl 6-azido-6-deoxy-α-D-glucopyranoside (23701-87-3) + methyl 3-azido-3-deoxy-β-D-glucopyranoside (65784-76-1) + (2R,3S,4S,5R,6R)-2-(azidomethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol (87586-16-1) + (1α,2β,3α,4β,6β)-4,6-Diazido-1,2,3-cyclohexantriol (90899-14-2)

Guidance literature:

With hydrogenchloride; acetyl chloride; at 20 ℃; for 48h;

DOI:10.1246/cl.190772

Reference yield: 77.0%

(2R,3S,4S,5R,6R)-2-(azidomethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol (87586-16-1) → methyl 6-deoxy-6-tert-butoxycarbonylamino-β-D-glucopyranoside (68396-86-1,496811-81-5)

Guidance literature:

With hydrogen; palladium; In water; for 1h;

DOI:10.1246/bcsj.59.1397

Reference yield:

(2R,3S,4S,5R,6R)-2-(azidomethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol (87586-16-1) → 6-{4-[bis(2-chloroethyl)amino]benzenebutanoyl amido}-6-deoxy-D-glucopyranose

Guidance literature:

Multi-step reaction with 3 steps

1: hydrogen / palladium on carbon / ethanol / 1.5 h / 20 °C

2: 79 percent / triethylamine / ethanol / 4 h / 20 °C

3: 81 percent / hydrochloric acid / 0.42 h / 100 °C

With hydrogenchloride; hydrogen; triethylamine; palladium on activated charcoal; In ethanol;

DOI:10.1016/S0014-2999(96)00796-0

upstream raw materials:

methanol

1,3,6',3”-tetra-azido-kanamycin A

Downstream raw materials:

methyl 6-deoxy-6-tert-butoxycarbonylamino-β-D-glucopyranoside

methyl 6-{4-[bis(2-chloroethyl)amino]benzenebutanoylamido}-6-deoxy-β-D-glucopyranoside