methyl 2,3,4-tri-O-acetyl-6-deoxy-6-azido-β-D-glucopyranoside

Base Information

• Chemical Name: methyl 2,3,4-tri-O-acetyl-6-deoxy-6-azido-β-D-glucopyranoside
• CAS No.: 52109-82-7
• Molecular Formula: C₁₃H₁₉N₃O₈
• Molecular Weight: 345.309
• Mol file: 52109-82-7.mol

Synonyms:methyl 2,3,4-tri-O-acetyl-6-deoxy-6-azido-β-D-glucopyranoside

Chemical Property of methyl 2,3,4-tri-O-acetyl-6-deoxy-6-azido-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2,3,4-tri-O-acetyl-6-deoxy-6-azido-β-D-glucopyranoside

There total 1 articles about methyl 2,3,4-tri-O-acetyl-6-deoxy-6-azido-β-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:

acetic anhydride (108-24-7) + 6-azido-6-deoxy-1,2-O-isopropylidene-β-L-idofuranose (104652-58-6) → methyl 2,3,4-tri-O-acetyl-6-deoxy-6-azido-β-D-glucopyranoside (52109-82-7) + methyl 2,3,4-tri-O-acetyl-6-azido-6-deoxy-β-L-idopyranoside (21893-05-0)

Guidance literature:

With hydrogenchloride; Yield given. Multistep reaction. Yields of byproduct given; 1.) reflux, 1.5 h; 2.) pyridine, roomtemp., overnight;

DOI:10.1246/bcsj.59.1397

Reference yield:

methyl 2,3,4-tri-O-acetyl-6-deoxy-6-azido-β-D-glucopyranoside (52109-82-7) + acetic anhydride (108-24-7) → methyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (4860-85-9) + Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-methoxy-tetrahydro-pyran-4-yl ester (604-70-6)

Guidance literature:

With pyridine; nitrosyl hexafluorophosphate; sodium methylate; Yield given. Multistep reaction. Yields of byproduct given;

Reference yield:

methyl 2,3,4-tri-O-acetyl-6-deoxy-6-azido-β-D-glucopyranoside (52109-82-7) → methyl 6-deoxy-6-tert-butoxycarbonylamino-β-D-glucopyranoside (68396-86-1,496811-81-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / barium hydroxide octahydrate / methanol / 0.17 h / Ambient temperature

2: 77 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:

acetic anhydride

6-azido-6-deoxy-1,2-O-isopropylidene-β-L-idofuranose

Downstream raw materials:

methyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-methoxy-tetrahydro-pyran-4-yl ester

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