benzyl 2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3-O-allyl-6-O-benzyl-2-deoxy-α-D-glucopyranoside

Base Information

• Chemical Name: benzyl 2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3-O-allyl-6-O-benzyl-2-deoxy-α-D-glucopyranoside
• CAS No.: 112302-99-5
• Molecular Formula: C₃₉H₅₀N₂O₁₄
• Molecular Weight: 770.831
• Mol file: 112302-99-5.mol

Synonyms:benzyl 2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3-O-allyl-6-O-benzyl-2-deoxy-α-D-glucopyranoside

Chemical Property of benzyl 2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3-O-allyl-6-O-benzyl-2-deoxy-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl 2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3-O-allyl-6-O-benzyl-2-deoxy-α-D-glucopyranoside

There total 6 articles about benzyl 2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3-O-allyl-6-O-benzyl-2-deoxy-α-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: 82.0%

acetic anhydride (108-24-7) + benzyl 2-acetamido-3-O-allyl-4-O-(2-amino-2-deoxy-β-D-glucopyranosyl)-6-O-benzyl-2-deoxy-α-D-glucopyranoside (112303-00-1) → benzyl 2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3-O-allyl-6-O-benzyl-2-deoxy-α-D-glucopyranoside (112302-99-5)

Guidance literature:

In pyridine; for 20h; Ambient temperature;

DOI:10.1016/0008-6215(87)80165-9

Reference yield:

1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose (10022-13-6) → benzyl 2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3-O-allyl-6-O-benzyl-2-deoxy-α-D-glucopyranoside (112302-99-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 89 percent / HBr / CH₂Cl₂ / 2 h / 15 °C

2: 94.2 percent / silver trifluoromethanesulfonate / CH₂Cl₂ / 1.) -45 deg C, 170 min; 2.) -20, 30 min

3: 78 percent / butylamine / methanol / 12 h / 85 °C

4: 82 percent / pyridine / 20 h / Ambient temperature

With hydrogen bromide; silver trifluoromethanesulfonate; N-butylamine; In pyridine; methanol; dichloromethane;

DOI:10.1016/0008-6215(87)80165-9

Reference yield:

benzyl 2-acetamido-3-O-allyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside (60920-72-1) → benzyl 2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3-O-allyl-6-O-benzyl-2-deoxy-α-D-glucopyranoside (112302-99-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) sodium cyanoborohydride, 2.5 M HCl; 2.) 80 percent acetic acid / 1.) room temp., THF, ether, 5 h; 2.) 100 grad C, 1 h

2: 94.2 percent / silver trifluoromethanesulfonate / CH₂Cl₂ / 1.) -45 deg C, 170 min; 2.) -20, 30 min

3: 78 percent / butylamine / methanol / 12 h / 85 °C

4: 82 percent / pyridine / 20 h / Ambient temperature

With hydrogenchloride; silver trifluoromethanesulfonate; sodium cyanoborohydride; acetic acid; N-butylamine; In pyridine; methanol; dichloromethane;

DOI:10.1016/0008-6215(87)80165-9

upstream raw materials:

acetic anhydride

benzyl 2-acetamido-3-O-allyl-4-O-(2-amino-2-deoxy-β-D-glucopyranosyl)-6-O-benzyl-2-deoxy-α-D-glucopyranoside

1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose

benzyl 2-acetamido-3-O-allyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside

Downstream raw materials:

N-<2-O--glycoloyl>-L-α-aminobutanoyl-D-isoglutamine benzyl ester

N-[(2S,3R,4R,5S,6R)-2-((2R,3S,4R,5R,6S)-5-Acetylamino-4-allyloxy-6-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl]-N-benzyl-acetamide

benzyl 2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-6-O-benzyl-2-deoxy-3-O-<(methoxycarbonyl)methyl>-α-D-glucopyranoside

benzyl 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl-(1→4)-2-acetamido-6-O-benzyl-3-O-carboxymethyl-2-deoxy-α-D-glucopyranoside