2-acetamido-1-O-acetyl-2-deoxy-3,4,6-tri-O-benzyl-α-D-glucopyranose

Base Information

• Chemical Name: 2-acetamido-1-O-acetyl-2-deoxy-3,4,6-tri-O-benzyl-α-D-glucopyranose
• CAS No.: 4171-73-7
• Molecular Formula: C₃₁H₃₅NO₇
• Molecular Weight: 533.621
• Mol file: 4171-73-7.mol

Synonyms:2-acetamido-1-O-acetyl-2-deoxy-3,4,6-tri-O-benzyl-α-D-glucopyranose

Chemical Property of 2-acetamido-1-O-acetyl-2-deoxy-3,4,6-tri-O-benzyl-α-D-glucopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-acetamido-1-O-acetyl-2-deoxy-3,4,6-tri-O-benzyl-α-D-glucopyranose

There total 5 articles about 2-acetamido-1-O-acetyl-2-deoxy-3,4,6-tri-O-benzyl-α-D-glucopyranose 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: 17.0%

2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranosyl acetate (65760-01-2) → Benzyl 2-N-acetylamino-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside (4171-69-1) + 2-acetamido-1-O-acetyl-2-deoxy-3,4,6-tri-O-benzyl-α-D-glucopyranose (4171-73-7) + N-((3R,4R,5S,6R)-4,5-bis(benzyloxy)-6-(benzyloxymethyl)-2-hydroxy-tetrahydro-2H-pyran-3-yl)acetamide (4171-79-3,121123-45-3,4171-72-6)

Guidance literature:

With bismuth(lll) trifluoromethanesulfonate; In dichloromethane; at 40 ℃; for 168h;

DOI:10.1021/acs.joc.6b02305

Reference yield:

2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranosyl acetate (65760-01-2) → 2-acetamido-1-O-acetyl-2-deoxy-3,4,6-tri-O-benzyl-α-D-glucopyranose (4171-73-7)

Guidance literature:

Multi-step reaction with 2 steps

1: bismuth(lll) trifluoromethanesulfonate / dichloromethane / 168 h / 40 °C

2: pyridine / 20 h

With bismuth(lll) trifluoromethanesulfonate; pyridine; In dichloromethane;

DOI:10.1021/acs.joc.6b02305

Reference yield:

N-((3R,4R,5S,6R)-4,5-bis(benzyloxy)-6-(benzyloxymethyl)-2-hydroxy-tetrahydro-2H-pyran-3-yl)acetamide (4171-79-3,121123-45-3,4171-72-6) + acetic anhydride (108-24-7) → 2-acetamido-1-O-acetyl-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranose (10583-63-8) + 2-acetamido-1-O-acetyl-2-deoxy-3,4,6-tri-O-benzyl-α-D-glucopyranose (4171-73-7)

Guidance literature:

N-((3R,4R,5S,6R)-4,5-bis(benzyloxy)-6-(benzyloxymethyl)-2-hydroxy-tetrahydro-2H-pyran-3-yl)acetamide; With pyridine; pyridine hydrochloride; at 100 ℃; for 0.25h;

acetic anhydride; for 0.25h; Temperature;

DOI:10.1021/acs.joc.6b02305

upstream raw materials:

N-((3R,4R,5S,6R)-4,5-bis(benzyloxy)-6-(benzyloxymethyl)-2-hydroxy-tetrahydro-2H-pyran-3-yl)acetamide

acetic anhydride

2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranosyl acetate

Downstream raw materials:

2-propenyl 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside

3-β-cholestanyl 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside

2-methyl-(3,4,6-tri-O-benzyl-1,2-dideoxy-α-D-glucopyrano)-<2,1-d>-2-oxazoline

3,4,6-tri-O-benzyl-2-acetamido-2-deoxyamino-α-D-glucopyranose