2,5-diazido-3-O-(4-azido-2,3-di-O-benzyl-4-deoxy-α-D-glucopyranosyl)-2,5-dideoxy-L-iditol

Base Information

• Chemical Name: 2,5-diazido-3-O-(4-azido-2,3-di-O-benzyl-4-deoxy-α-D-glucopyranosyl)-2,5-dideoxy-L-iditol
• CAS No.: 122079-84-9
• Molecular Formula: C₂₆H₃₃N₉O₈
• Molecular Weight: 599.604
• Mol file: 122079-84-9.mol

Synonyms:2,5-diazido-3-O-(4-azido-2,3-di-O-benzyl-4-deoxy-α-D-glucopyranosyl)-2,5-dideoxy-L-iditol

Chemical Property of 2,5-diazido-3-O-(4-azido-2,3-di-O-benzyl-4-deoxy-α-D-glucopyranosyl)-2,5-dideoxy-L-iditol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,5-diazido-3-O-(4-azido-2,3-di-O-benzyl-4-deoxy-α-D-glucopyranosyl)-2,5-dideoxy-L-iditol

There total 12 articles about 2,5-diazido-3-O-(4-azido-2,3-di-O-benzyl-4-deoxy-α-D-glucopyranosyl)-2,5-dideoxy-L-iditol 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: 65.0%

2,5-diazido-3-O-(4-azido-2,3-di-O-benzyl-6-O-propionyl-α-D-glucopyranosyl)-1,6-di-O-benzoyl-2,5-dideoxy-L-iditol (122079-83-8) → 2,5-diazido-3-O-(4-azido-2,3-di-O-benzyl-4-deoxy-α-D-glucopyranosyl)-2,5-dideoxy-L-iditol (122079-84-9)

Guidance literature:

With methanol; sodium methylate; at 40 ℃; for 0.5h;

DOI:10.1016/0008-6215(89)84037-6

Reference yield:

benzyl chloride (100-44-7) → 2,5-diazido-3-O-(4-azido-2,3-di-O-benzyl-4-deoxy-α-D-glucopyranosyl)-2,5-dideoxy-L-iditol (122079-84-9)

Guidance literature:

Multi-step reaction with 9 steps

1: 75.5 percent / KOH / dimethylformamide / 2 h / 30 - 35 °C

2: 92.3 percent / 75percent CH₃COOH / 0.5 h / 100 °C

3: 74 percent / pyridine / 5 deg C, then room t.

4: 96.3 percent / pyridine / 4 h / 30 - 32 °C

5: 84 percent / NaN₃ / dimethylformamide / 2 h / 120 - 125 °C

6: 74.5 percent / conc. H₂SO₄ / 1 h / Ambient temperature

7: 83 percent / Cl₂CHOCH₃ / ZnCl₂ / 20 h / Heating

8: 24 percent / molecular sieves(5 Angstroem) / HgO, HgBr₂ / CH₂Cl₂ / 1 h, room t., then 20 h, room t. and 40 h, reflux

9: 65 percent / 1M NaOMe/MeOH / 0.5 h / 40 °C

With pyridine; methanol; potassium hydroxide; sodium azide; Dichloromethyl methyl ether; 5A molecular sieve; sulfuric acid; sodium methylate; acetic acid; mercury dibromide; mercury(II) oxide; zinc(II) chloride; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(89)84037-6

Reference yield:

methyl 4,6-O-isopropylidene-β-D-galacytopyranoside (20688-90-8) → 2,5-diazido-3-O-(4-azido-2,3-di-O-benzyl-4-deoxy-α-D-glucopyranosyl)-2,5-dideoxy-L-iditol (122079-84-9)

Guidance literature:

Multi-step reaction with 9 steps

1: 75.5 percent / KOH / dimethylformamide / 2 h / 30 - 35 °C

2: 92.3 percent / 75percent CH₃COOH / 0.5 h / 100 °C

3: 74 percent / pyridine / 5 deg C, then room t.

4: 96.3 percent / pyridine / 4 h / 30 - 32 °C

5: 84 percent / NaN₃ / dimethylformamide / 2 h / 120 - 125 °C

6: 74.5 percent / conc. H₂SO₄ / 1 h / Ambient temperature

7: 83 percent / Cl₂CHOCH₃ / ZnCl₂ / 20 h / Heating

8: 24 percent / molecular sieves(5 Angstroem) / HgO, HgBr₂ / CH₂Cl₂ / 1 h, room t., then 20 h, room t. and 40 h, reflux

9: 65 percent / 1M NaOMe/MeOH / 0.5 h / 40 °C

With pyridine; methanol; potassium hydroxide; sodium azide; Dichloromethyl methyl ether; 5A molecular sieve; sulfuric acid; sodium methylate; acetic acid; mercury dibromide; mercury(II) oxide; zinc(II) chloride; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(89)84037-6

upstream raw materials:

2,5-diazido-3-O-(4-azido-2,3-di-O-benzyl-6-O-propionyl-α-D-glucopyranosyl)-1,6-di-O-benzoyl-2,5-dideoxy-L-iditol

methyl 4,6-O-isopropylidene-β-D-galacytopyranoside

benzyl chloride

methyl 2,3-di-O-benzyl-6-O-propionyl-β-D-galactopyranoside