4-Nitrophenyl O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->2)-O-(3,4-di-O-acetyl-6-O-methyl-α-D-mannopyranosyl)-(1->6)-2,3-di-O-acetyl-β-D-glucopyranoside

Base Information

• Chemical Name: 4-Nitrophenyl O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->2)-O-(3,4-di-O-acetyl-6-O-methyl-α-D-mannopyranosyl)-(1->6)-2,3-di-O-acetyl-β-D-glucopyranoside
• CAS No.: 150161-22-1
• Molecular Formula: C₄₁H₅₄N₂O₂₅
• Molecular Weight: 974.878
• Mol file: 150161-22-1.mol

Synonyms:4-Nitrophenyl O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->2)-O-(3,4-di-O-acetyl-6-O-methyl-α-D-mannopyranosyl)-(1->6)-2,3-di-O-acetyl-β-D-glucopyranoside

Chemical Property of 4-Nitrophenyl O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->2)-O-(3,4-di-O-acetyl-6-O-methyl-α-D-mannopyranosyl)-(1->6)-2,3-di-O-acetyl-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-Nitrophenyl O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->2)-O-(3,4-di-O-acetyl-6-O-methyl-α-D-mannopyranosyl)-(1->6)-2,3-di-O-acetyl-β-D-glucopyranoside

There total 12 articles about 4-Nitrophenyl O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->2)-O-(3,4-di-O-acetyl-6-O-methyl-α-D-mannopyranosyl)-(1->6)-2,3-di-O-acetyl-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: 62.0%

4-nitrophenyl 2,3-di-O-acetyl-β-D-glucopyranoside (40837-80-7) + O-(2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->2)-3,4-di-O-acetyl-6-O-methyl-α-D-mannopyranosyl bromide (150161-21-0) → 4-Nitrophenyl O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->2)-O-(3,4-di-O-acetyl-6-O-methyl-α-D-mannopyranosyl)-(1->6)-2,3-di-O-acetyl-β-D-glucopyranoside (150161-22-1)

Guidance literature:

With 2,4,6-trimethyl-pyridine; 4 A molecular sieve; silver trifluoromethanesulfonate; In dichloromethane; at 0 ℃; for 6h;

DOI:10.1016/0008-6215(93)84079-L

Reference yield:

methyl 4-O-benzyl-2,3-O-isopropylidene-α-D-mannopyranoside (82185-79-3) → 4-Nitrophenyl O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->2)-O-(3,4-di-O-acetyl-6-O-methyl-α-D-mannopyranosyl)-(1->6)-2,3-di-O-acetyl-β-D-glucopyranoside (150161-22-1)

Guidance literature:

Multi-step reaction with 11 steps

1: 77 percent / BaO, Ba(OH)2*8H₂O / dimethylformamide / 16 h / Ambient temperature

2: 63 percent / CF₃CO₂H, water / CHCl₃ / 1 h / Ambient temperature

3: 1) Bu₂SnO / 1) MeOH, 1 h, reflux, 2) DMF, 5 h, 110 deg C

4: 1) 4A molecular sieves, N-iodosuccinimide, 2) Cf₃So₃H / 1) CH₂Cl₂, 30 min, r.t., 2) 2 h, r.t.

5: N₂H₄*H₂O / ethanol / 3 h / Heating

6: pyridine / Ambient temperature

7: 91 percent / H₂ / 10percent Pd/C / acetic acid / 48 h / 2587.7 Torr / Ambient temperature

8: 93 percent / pyridine / Ambient temperature

9: 89 percent / conc. H₂SO₄ / 17 h / Ambient temperature

10: 87 percent / 31percentHBr/AcOH / CH₂Cl₂ / 12 h / 0 °C

11: 62 percent / s-collidine, CF₃SO₃Ag, 4A molecular sieves / CH₂Cl₂ / 6 h / 0 °C

With pyridine; 2,4,6-trimethyl-pyridine; barium dihydroxide; N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; sulfuric acid; water; hydrogen bromide; hydrogen; silver trifluoromethanesulfonate; di(n-butyl)tin oxide; hydrazine hydrate; acetic acid; trifluoroacetic acid; barium(II) oxide; palladium on activated charcoal; In ethanol; dichloromethane; chloroform; acetic acid; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(93)84079-L

Reference yield:

methyl 6-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-α-D-mannopyranoside (131089-35-5) → 4-Nitrophenyl O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->2)-O-(3,4-di-O-acetyl-6-O-methyl-α-D-mannopyranosyl)-(1->6)-2,3-di-O-acetyl-β-D-glucopyranoside (150161-22-1)

Guidance literature:

Multi-step reaction with 13 steps

1: 64.1 percent / Ag₂O / dimethylformamide / 48 h / 45 °C

2: 82 percent / Bu₄NF / tetrahydrofuran / 6 h / Ambient temperature

3: 77 percent / BaO, Ba(OH)2*8H₂O / dimethylformamide / 16 h / Ambient temperature

4: 63 percent / CF₃CO₂H, water / CHCl₃ / 1 h / Ambient temperature

5: 1) Bu₂SnO / 1) MeOH, 1 h, reflux, 2) DMF, 5 h, 110 deg C

6: 1) 4A molecular sieves, N-iodosuccinimide, 2) Cf₃So₃H / 1) CH₂Cl₂, 30 min, r.t., 2) 2 h, r.t.

7: N₂H₄*H₂O / ethanol / 3 h / Heating

8: pyridine / Ambient temperature

9: 91 percent / H₂ / 10percent Pd/C / acetic acid / 48 h / 2587.7 Torr / Ambient temperature

10: 93 percent / pyridine / Ambient temperature

11: 89 percent / conc. H₂SO₄ / 17 h / Ambient temperature

12: 87 percent / 31percentHBr/AcOH / CH₂Cl₂ / 12 h / 0 °C

13: 62 percent / s-collidine, CF₃SO₃Ag, 4A molecular sieves / CH₂Cl₂ / 6 h / 0 °C

With pyridine; 2,4,6-trimethyl-pyridine; barium dihydroxide; N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; sulfuric acid; tetrabutyl ammonium fluoride; water; hydrogen bromide; hydrogen; silver trifluoromethanesulfonate; di(n-butyl)tin oxide; hydrazine hydrate; acetic acid; trifluoroacetic acid; barium(II) oxide; silver(l) oxide; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; chloroform; acetic acid; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(93)84079-L

upstream raw materials:

4-nitrophenyl 2,3-di-O-acetyl-β-D-glucopyranoside

O-(2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->2)-3,4-di-O-acetyl-6-O-methyl-α-D-mannopyranosyl bromide

methyl 4-O-benzyl-2,3-O-isopropylidene-α-D-mannopyranoside

methyl 6-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-α-D-mannopyranoside