2-(Acetylamino)-4-O-[2-(acetylamino)-2-deoxy-3,4,6-tris-O-(phenylmethyl)-beta-D-glucopyranosyl]-2-deoxy-3,6-bis-O-(phenylmethyl)-beta-D-glucopyranosyl azide

Base Information

• Chemical Name: 2-(Acetylamino)-4-O-[2-(acetylamino)-2-deoxy-3,4,6-tris-O-(phenylmethyl)-beta-D-glucopyranosyl]-2-deoxy-3,6-bis-O-(phenylmethyl)-beta-D-glucopyranosyl azide
• CAS No.: 214467-61-5
• Molecular Formula: C₅₁H₅₇N₅O₁₀
• Molecular Weight: 900.041
• DSSTox Substance ID: DTXSID601100297
• Mol file: 214467-61-5.mol

Synonyms:DTXSID601100297;214467-61-5

Chemical Property of 2-(Acetylamino)-4-O-[2-(acetylamino)-2-deoxy-3,4,6-tris-O-(phenylmethyl)-beta-D-glucopyranosyl]-2-deoxy-3,6-bis-O-(phenylmethyl)-beta-D-glucopyranosyl azide

Chemical Property:

• XLogP3: 6.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 22
• Exact Mass: 899.41054303
• Heavy Atom Count: 66
• Complexity: 1460

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=O)NC1C(C(C(OC1N=[N+]=[N-])COCC2=CC=CC=C2)OC3C(C(C(C(O3)COCC4=CC=CC=C4)OCC5=CC=CC=C5)OCC6=CC=CC=C6)NC(=O)C)OCC7=CC=CC=C7
• Isomeric SMILES: CC(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@H]1N=[N+]=[N-])COCC2=CC=CC=C2)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)COCC4=CC=CC=C4)OCC5=CC=CC=C5)OCC6=CC=CC=C6)NC(=O)C)OCC7=CC=CC=C7

Technology Process of 2-(Acetylamino)-4-O-[2-(acetylamino)-2-deoxy-3,4,6-tris-O-(phenylmethyl)-beta-D-glucopyranosyl]-2-deoxy-3,6-bis-O-(phenylmethyl)-beta-D-glucopyranosyl azide

There total 10 articles about 2-(Acetylamino)-4-O-[2-(acetylamino)-2-deoxy-3,4,6-tris-O-(phenylmethyl)-beta-D-glucopyranosyl]-2-deoxy-3,6-bis-O-(phenylmethyl)-beta-D-glucopyranosyl azide 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) + C47H53N5O8 → O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl azide (214467-61-5)

Guidance literature:

In pyridine; at 20 ℃;

DOI:10.1016/j.carres.2008.08.024

Reference yield:

benzyl bromide (100-39-0) → O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl azide (214467-61-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 89 percent / Ag₂O / dimethylformamide

2: 90 percent / NIS, AgOTf / -40 °C

3: ethylenediamine

With N-iodo-succinimide; silver trifluoromethanesulfonate; ethylenediamine; silver(l) oxide; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(98)01540-8

Reference yield:

ethyl 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (138730-66-2) → O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl azide (214467-61-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 92 percent / trimethylsilyl azide, methyl triflate, molecular sieves / CH₂Cl₂

2: 90 percent / K₂CO₃ / tetrahydrofuran; methanol

3: 90 percent / NIS, AgOTf / -40 °C

4: ethylenediamine

With N-iodo-succinimide; molecular sieve; trimethylsilylazide; silver trifluoromethanesulfonate; potassium carbonate; ethylenediamine; methyl trifluoromethanesulfonate; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1016/S0040-4039(98)01540-8

upstream raw materials:

benzyl bromide

3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide

ethyl 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide

Downstream raw materials:

N²-(tert-butoxycarbonyl)-N⁴-[2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl-(1-4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl]-L-asparagine fluorenylmethyl ester