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

Base Information

Chemical Name: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
CAS No.:112302-95-1
Molecular Formula:C₅₄H₆₂N₂O₁₃
Molecular Weight:947.092
Hs Code.:

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

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 12 articles about 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 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: 93.0%

: 186581-53-3,908094-01-9,334-88-3
diazomethane

: 112302-96-2
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

: 112302-95-1
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

Guidance literature:: In methanol; diethyl ether; dichloromethane; at 0 ℃; for 1h;
DOI:10.1021/acs.jmedchem.7b00593

Reference yield:

: 73440-91-2
benzyl 2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-3-O-allyl-6-O-benzyl-2-deoxy-α-D-glucopyranoside

: 112302-95-1
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

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) tris(triphenylphosphine)rhodium(I) chloride; 2.) formic acid / 1.) 3 h, reflux, ethanol, toluene, water; 2.) 1 h, reflux

2: 1.) NaH / 1.) dioxane, 1 h, 96 deg C; 2.) dioxane, 65 deg C, 3.5 h, 12 h, room temp

3: 62.7 percent / methanol; CHCl₃ / Ambient temperature

With Wilkinson's catalyst; formic acid; sodium hydride; In methanol; chloroform;
DOI:10.1016/0008-6215(87)80165-9

Reference yield:

: 10022-13-6
1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose

: 112302-95-1
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

Guidance literature:: Multi-step reaction with 9 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

5: 92 percent / 0.01 M NaOMe / methanol / 12 h / 5 °C

6: 71 percent / barium hydroxide / dimethylformamide / 10 h / Ambient temperature; Irradiation

7: 1.) tris(triphenylphosphine)rhodium(I) chloride; 2.) formic acid / 1.) 3 h, reflux, ethanol, toluene, water; 2.) 1 h, reflux

8: 1.) NaH / 1.) dioxane, 1 h, 96 deg C; 2.) dioxane, 65 deg C, 3.5 h, 12 h, room temp

9: 62.7 percent / methanol; CHCl₃ / Ambient temperature

With barium dihydroxide; Wilkinson's catalyst; formic acid; hydrogen bromide; sodium methylate; silver trifluoromethanesulfonate; sodium hydride; N-butylamine; In pyridine; methanol; dichloromethane; chloroform; N,N-dimethyl-formamide;
DOI:10.1016/0008-6215(87)80165-9