methyl 3-O-(4'-azido-2',3'-di-O-acetyl-4',6'-dideoxy-β-D-glucopyranosyl)-2-azido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside

Base Information

• Chemical Name: methyl 3-O-(4'-azido-2',3'-di-O-acetyl-4',6'-dideoxy-β-D-glucopyranosyl)-2-azido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside
• CAS No.: 887497-53-2
• Molecular Formula: C₂₄H₃₀N₆O₁₀
• Molecular Weight: 562.536
• Mol file: 887497-53-2.mol

Synonyms:methyl 3-O-(4'-azido-2',3'-di-O-acetyl-4',6'-dideoxy-β-D-glucopyranosyl)-2-azido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside

Chemical Property of methyl 3-O-(4'-azido-2',3'-di-O-acetyl-4',6'-dideoxy-β-D-glucopyranosyl)-2-azido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 3-O-(4'-azido-2',3'-di-O-acetyl-4',6'-dideoxy-β-D-glucopyranosyl)-2-azido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside

There total 1 articles about methyl 3-O-(4'-azido-2',3'-di-O-acetyl-4',6'-dideoxy-β-D-glucopyranosyl)-2-azido-4,6-O-benzylidene-2-deoxy-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: 92.0%

Acetic acid (3R,4S,5R,6R)-4-acetoxy-5-azido-6-methyl-2-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester + methyl 2-azido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside (274260-02-5) → methyl 3-O-(4'-azido-2',3'-di-O-acetyl-4',6'-dideoxy-β-D-glucopyranosyl)-2-azido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside (887497-53-2)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In dichloromethane; at -60 - -10 ℃;

DOI:10.1039/b517725a

Reference yield:

methyl 3-O-(4'-azido-2',3'-di-O-acetyl-4',6'-dideoxy-β-D-glucopyranosyl)-2-azido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside (887497-53-2) → (2S,3R,4S,5S,6R)-5-Amino-2-[(2R,3R,4R,5R,6R)-3-amino-5-((2R,3R,4R,5R,6R)-3-amino-6-aminomethyl-4,5-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-6-aminomethyl-2-methoxy-tetrahydro-pyran-4-yloxy]-6-methyl-tetrahydro-pyran-3,4-diol

Guidance literature:

Multi-step reaction with 6 steps

1: aq. AcOH / 3 h / 80 - 85 °C

2: pyridine / 4 h / 20 °C

3: 64 mg / NaN₃ / dimethylformamide / 80 - 90 °C

4: 4 Angstroem molecular sieves; trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂; diethyl ether / -60 - -10 °C

5: 8.5 mg / CH₃ONa / aq. methanol / 20 °C / pH 12 - 13

6: pyridine; H₂ / Pd/C / 18 h

With pyridine; sodium azide; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; hydrogen; sodium methylate; acetic acid; palladium on activated charcoal; In methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1039/b517725a

Reference yield:

methyl 3-O-(4'-azido-2',3'-di-O-acetyl-4',6'-dideoxy-β-D-glucopyranosyl)-2-azido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside (887497-53-2) → (2S,3R,4S,5S,6R)-5-Amino-2-[(2R,3R,4R,5S,6R)-3-amino-5-((2R,3R,4R,5R,6R)-3-amino-6-aminomethyl-4,5-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-4-yloxy]-6-methyl-tetrahydro-pyran-3,4-diol

Guidance literature:

Multi-step reaction with 5 steps

1: aq. AcOH / 3 h / 80 - 85 °C

2: 33 mg / pyridine / 2 h / 20 °C

3: 4 Angstroem molecular sieves; trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂; diethyl ether / -60 - -10 °C

4: 20.0 mg / CH₃ONa / aq. methanol / 20 °C / pH 12 - 13

5: pyridine; H₂ / Pd/C / 18 h

With pyridine; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; hydrogen; sodium methylate; acetic acid; palladium on activated charcoal; In methanol; diethyl ether; dichloromethane;

DOI:10.1039/b517725a

upstream raw materials:

methyl 2-azido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside

Downstream raw materials:

methyl 3-O-(4''-azido-4'',6''-dideoxy-β-D-glucopyranosyl)-4-O-(2',6'-diazido-3',4'-di-O-benzyl-2',6'-dideoxy-α-D-glucopyranosyl)-2-azido-2-deoxy-β-D-glucopyranoside

methyl 3-O-(4''-azido-4'',6''-dideoxy-β-D-glucopyranosyl)-4-O-(2',6'-diazido-3',4'-di-O-benzyl-2',6'-dideoxy-α-D-glucopyranosyl)-2,6-diazido-2,6-dideoxy-β-D-glucopyranoside

Acetic acid (2S,3R,4S,5R,6R)-4-acetoxy-5-azido-2-[(2R,3R,4R,5R,6R)-3-azido-5-((2R,3R,4R,5R,6R)-3-azido-6-azidomethyl-4,5-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-6-azidomethyl-2-methoxy-tetrahydro-pyran-4-yloxy]-6-methyl-tetrahydro-pyran-3-yl ester