O-(2-Acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)-(1->2)-O-<(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)-(1->6)>-3,4-di-O-benzyl-α-D-mannopyranose

Base Information

• Chemical Name: O-(2-Acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)-(1->2)-O-<(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)-(1->6)>-3,4-di-O-benzyl-α-D-mannopyranose
• CAS No.: 136945-03-4
• Molecular Formula: C₄₈H₆₂N₂O₂₂
• Molecular Weight: 1019.02
• Mol file: 136945-03-4.mol

Synonyms:

Chemical Property of O-(2-Acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)-(1->2)-O-<(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)-(1->6)>-3,4-di-O-benzyl-α-D-mannopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of O-(2-Acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)-(1->2)-O-<(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)-(1->6)>-3,4-di-O-benzyl-α-D-mannopyranose

There total 10 articles about O-(2-Acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)-(1->2)-O-<(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)-(1->6)>-3,4-di-O-benzyl-α-D-mannopyranose 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:

benzyl bromide (100-39-0) → O-(2-Acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)-(1->2)-O-<(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)-(1->6)>-3,4-di-O-benzyl-α-D-mannopyranose (136945-03-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 61 percent / NaH / dimethylformamide / a) -10 deg C, 3 h, b) 0 deg C, 3 h, c) 5 deg C, 4 h

2: 97 percent / 4 A molecular sieves, trimethylsilyltriflate / CH₂Cl₂ / 1 h / Ambient temperature

3: 87 percent / Bu₄NF / various solvent(s) / 12 h / Ambient temperature

4: 100 percent / NaOMe / methanol / 16 h / Ambient temperature

5: 1) 2,4,6-trimethylpyridine, Ag-triflate, 4 Angstroem molecular sieves / 1) CH₂Cl₂, r.t, 1 h, 2) -10 deg C, 14 h

6: 1) BuNH₂, 2) pyridine / 1) MeOH, reflux, 3 d, 2) 7 deg C, 7 h

7: 2) I₂ / 1) 2)2>PF₆ / 1) oxolane, r.t., 30 min, 2) H₂O, r.t., 10 min

With pyridine; 2,4,6-trimethyl-pyridine; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; tetrabutyl ammonium fluoride; iodine; sodium methylate; silver trifluoromethanesulfonate; sodium hydride; N-butylamine; (1,5-cyclooctadiene)bis(methyldiphenylphosphine) iridium hexafluorophosphate; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(92)84169-S

Reference yield:

1,2-O-(Allyloxyethyliden)-β-D-mannopyranose (136944-92-8) → O-(2-Acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)-(1->2)-O-<(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)-(1->6)>-3,4-di-O-benzyl-α-D-mannopyranose (136945-03-4)

Guidance literature:

Multi-step reaction with 8 steps

1: 98 percent / imidazole / dimethylformamide / 1.5 h / Ambient temperature

2: 61 percent / NaH / dimethylformamide / a) -10 deg C, 3 h, b) 0 deg C, 3 h, c) 5 deg C, 4 h

3: 97 percent / 4 A molecular sieves, trimethylsilyltriflate / CH₂Cl₂ / 1 h / Ambient temperature

4: 87 percent / Bu₄NF / various solvent(s) / 12 h / Ambient temperature

5: 100 percent / NaOMe / methanol / 16 h / Ambient temperature

6: 1) 2,4,6-trimethylpyridine, Ag-triflate, 4 Angstroem molecular sieves / 1) CH₂Cl₂, r.t, 1 h, 2) -10 deg C, 14 h

7: 1) BuNH₂, 2) pyridine / 1) MeOH, reflux, 3 d, 2) 7 deg C, 7 h

8: 2) I₂ / 1) 2)2>PF₆ / 1) oxolane, r.t., 30 min, 2) H₂O, r.t., 10 min

With pyridine; 1H-imidazole; 2,4,6-trimethyl-pyridine; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; tetrabutyl ammonium fluoride; iodine; sodium methylate; silver trifluoromethanesulfonate; sodium hydride; N-butylamine; (1,5-cyclooctadiene)bis(methyldiphenylphosphine) iridium hexafluorophosphate; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(92)84169-S

Reference yield:

Allyl-2-O-acetyl-3,4-di-O-benzyl-α-D-mannopyranosid (136944-96-2) → O-(2-Acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)-(1->2)-O-<(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)-(1->6)>-3,4-di-O-benzyl-α-D-mannopyranose (136945-03-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 100 percent / NaOMe / methanol / 16 h / Ambient temperature

2: 1) 2,4,6-trimethylpyridine, Ag-triflate, 4 Angstroem molecular sieves / 1) CH₂Cl₂, r.t, 1 h, 2) -10 deg C, 14 h

3: 1) BuNH₂, 2) pyridine / 1) MeOH, reflux, 3 d, 2) 7 deg C, 7 h

4: 2) I₂ / 1) 2)2>PF₆ / 1) oxolane, r.t., 30 min, 2) H₂O, r.t., 10 min

With pyridine; 2,4,6-trimethyl-pyridine; 4 A molecular sieve; iodine; sodium methylate; silver trifluoromethanesulfonate; N-butylamine; (1,5-cyclooctadiene)bis(methyldiphenylphosphine) iridium hexafluorophosphate; In methanol;

DOI:10.1016/0008-6215(92)84169-S

upstream raw materials:

Allyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)-(1->2)-O-<(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)-(1->6)>-3,4-di-O-benzyl-α-D-mannopyranosid

benzyl bromide

Allyl-O-(3,4,6-tri-O-acetyl-2-desoxy-2-phthalimido-β-D-glucopyranosyl)-(1->2)-O-<3,4,6-tri-O-acetyl-2-desoxy-2-phthalimido-β-D-glucopyranosyl)-(1->6)>-3,4-di-O-benzyl-α-D-mannopyranosid

1,2-O-(Allyloxyethyliden)-β-D-mannopyranose