octyl O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1<*>2)-O-(3,4-di-O-acetyl-6-deoxy-6-fluoro-α-D-mannopyranosyl)-(1<*>6)-2,3,4-tri-O-benzyl-β-D-glucopyranoside

Base Information

• Chemical Name: octyl O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1<*>2)-O-(3,4-di-O-acetyl-6-deoxy-6-fluoro-α-D-mannopyranosyl)-(1<*>6)-2,3,4-tri-O-benzyl-β-D-glucopyranoside
• CAS No.: 161767-38-0
• Molecular Formula: C₅₉H₇₈FNO₂₀
• Molecular Weight: 1140.26

Synonyms:

Chemical Property of octyl O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1<*>2)-O-(3,4-di-O-acetyl-6-deoxy-6-fluoro-α-D-mannopyranosyl)-(1<*>6)-2,3,4-tri-O-benzyl-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of octyl O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1<*>2)-O-(3,4-di-O-acetyl-6-deoxy-6-fluoro-α-D-mannopyranosyl)-(1<*>6)-2,3,4-tri-O-benzyl-β-D-glucopyranoside

There total 10 articles about octyl O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1<*>2)-O-(3,4-di-O-acetyl-6-deoxy-6-fluoro-α-D-mannopyranosyl)-(1<*>6)-2,3,4-tri-O-benzyl-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:

methyl 4-O-benzyl-2,3-O-isopropylidene-α-D-mannopyranoside (82185-79-3) → octyl O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1<*>2)-O-(3,4-di-O-acetyl-6-deoxy-6-fluoro-α-D-mannopyranosyl)-(1<*>6)-2,3,4-tri-O-benzyl-β-D-glucopyranoside (161767-38-0)

Guidance literature:

Multi-step reaction with 11 steps

1: 44 percent / N,N-diethylaminosulfur trifluoride / CH₂Cl₂ / 2 h / -40 - 20 °C

2: 93 percent / aq. CF₃CO₂H / CHCl₃ / 4 h / Ambient temperature

3: 1.) dibutyltin oxide / 1.) MeOH, reflux, 1 h, 2.) DMF, 100 deg C, 1 h

4: 98 percent / silver trifluoromethanesulfonate, sym-collidine, mol. sieves 4A / CH₂Cl₂ / 2.25 h / -50 - 20 °C

5: 85percent hydrazine-hydrate / ethanol / 3 h / Heating

6: pyridine / Ambient temperature

7: 98 percent / H₂ / 10percent Pd/C / aq. ethanol; acetic acid / 18 h / 760 Torr / Ambient temperature

8: 94 percent / pyridine / Ambient temperature

9: 85 percent / H₂SO₄ / 12 h / Ambient temperature

10: 86 percent / HCl gas, Ac₂O / CH₂Cl₂ / 12 h / Ambient temperature

11: 27.1 mg / mercuric cyanide, mercuric bromide, mol. sieves 4A / nitromethane / 15 h / Ambient temperature

With pyridine; 2,4,6-trimethyl-pyridine; hydrogenchloride; diethylamino-sulfur trifluoride; 4 A molecular sieve; sulfuric acid; hydrogen; silver trifluoromethanesulfonate; mercury(II) cyanide; acetic anhydride; di(n-butyl)tin oxide; hydrazine hydrate; trifluoroacetic acid; mercury dibromide; palladium on activated charcoal; In nitromethane; ethanol; dichloromethane; chloroform; acetic acid;

DOI:10.1016/S0957-4166(00)80389-4

Reference yield:

methyl-4-O-benzyl-6-deoxy-6-fluoro-2,3-O-isopropylidene-α-D-mannopyranoside (161767-27-7) → octyl O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1<*>2)-O-(3,4-di-O-acetyl-6-deoxy-6-fluoro-α-D-mannopyranosyl)-(1<*>6)-2,3,4-tri-O-benzyl-β-D-glucopyranoside (161767-38-0)

Guidance literature:

Multi-step reaction with 10 steps

1: 93 percent / aq. CF₃CO₂H / CHCl₃ / 4 h / Ambient temperature

2: 1.) dibutyltin oxide / 1.) MeOH, reflux, 1 h, 2.) DMF, 100 deg C, 1 h

3: 98 percent / silver trifluoromethanesulfonate, sym-collidine, mol. sieves 4A / CH₂Cl₂ / 2.25 h / -50 - 20 °C

4: 85percent hydrazine-hydrate / ethanol / 3 h / Heating

5: pyridine / Ambient temperature

6: 98 percent / H₂ / 10percent Pd/C / aq. ethanol; acetic acid / 18 h / 760 Torr / Ambient temperature

7: 94 percent / pyridine / Ambient temperature

8: 85 percent / H₂SO₄ / 12 h / Ambient temperature

9: 86 percent / HCl gas, Ac₂O / CH₂Cl₂ / 12 h / Ambient temperature

10: 27.1 mg / mercuric cyanide, mercuric bromide, mol. sieves 4A / nitromethane / 15 h / Ambient temperature

With pyridine; 2,4,6-trimethyl-pyridine; hydrogenchloride; 4 A molecular sieve; sulfuric acid; hydrogen; silver trifluoromethanesulfonate; mercury(II) cyanide; acetic anhydride; di(n-butyl)tin oxide; hydrazine hydrate; trifluoroacetic acid; mercury dibromide; palladium on activated charcoal; In nitromethane; ethanol; dichloromethane; chloroform; acetic acid;

DOI:10.1016/S0957-4166(00)80389-4

Reference yield:

methyl-4-O-benzyl-6-deoxy-6-fluoro-α-D-mannopyranoside (161767-28-8) → octyl O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1<*>2)-O-(3,4-di-O-acetyl-6-deoxy-6-fluoro-α-D-mannopyranosyl)-(1<*>6)-2,3,4-tri-O-benzyl-β-D-glucopyranoside (161767-38-0)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) dibutyltin oxide / 1.) MeOH, reflux, 1 h, 2.) DMF, 100 deg C, 1 h

2: 98 percent / silver trifluoromethanesulfonate, sym-collidine, mol. sieves 4A / CH₂Cl₂ / 2.25 h / -50 - 20 °C

3: 85percent hydrazine-hydrate / ethanol / 3 h / Heating

4: pyridine / Ambient temperature

5: 98 percent / H₂ / 10percent Pd/C / aq. ethanol; acetic acid / 18 h / 760 Torr / Ambient temperature

6: 94 percent / pyridine / Ambient temperature

7: 85 percent / H₂SO₄ / 12 h / Ambient temperature

8: 86 percent / HCl gas, Ac₂O / CH₂Cl₂ / 12 h / Ambient temperature

9: 27.1 mg / mercuric cyanide, mercuric bromide, mol. sieves 4A / nitromethane / 15 h / Ambient temperature

With pyridine; 2,4,6-trimethyl-pyridine; hydrogenchloride; 4 A molecular sieve; sulfuric acid; hydrogen; silver trifluoromethanesulfonate; mercury(II) cyanide; acetic anhydride; di(n-butyl)tin oxide; hydrazine hydrate; mercury dibromide; palladium on activated charcoal; In nitromethane; ethanol; dichloromethane; acetic acid;

DOI:10.1016/S0957-4166(00)80389-4

upstream raw materials:

octyl 2,3,4-tri-O-benzyl-β-D-glucopyranoside

methyl 2-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3,4-di-O-acetyl-6-deoxy-6-fluoro-α-D-mannopyranosyl chloride

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

methyl-4-O-benzyl-6-deoxy-6-fluoro-α-D-mannopyranoside

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