O-(2-deoxy-2-acetamido-β-D-glucopyranosyl)-(1->4)-[O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->6)]-3-O-benzyl-2-deoxy-2-acetamido-β-D-glucopyranosyl azide

Base Information

Chemical Name:O-(2-deoxy-2-acetamido-β-D-glucopyranosyl)-(1->4)-[O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->6)]-3-O-benzyl-2-deoxy-2-acetamido-β-D-glucopyranosyl azide
CAS No.:622830-66-4
Molecular Formula:C₅₀H₆₁N₅O₁₄
Molecular Weight:956.059
Hs Code.:

Synonyms:O-(2-deoxy-2-acetamido-β-D-glucopyranosyl)-(1->4)-[O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->6)]-3-O-benzyl-2-deoxy-2-acetamido-β-D-glucopyranosyl azide

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Chemical Property of O-(2-deoxy-2-acetamido-β-D-glucopyranosyl)-(1->4)-[O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->6)]-3-O-benzyl-2-deoxy-2-acetamido-β-D-glucopyranosyl azide

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Technology Process of O-(2-deoxy-2-acetamido-β-D-glucopyranosyl)-(1->4)-[O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->6)]-3-O-benzyl-2-deoxy-2-acetamido-β-D-glucopyranosyl azide

There total 5 articles about O-(2-deoxy-2-acetamido-β-D-glucopyranosyl)-(1->4)-[O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->6)]-3-O-benzyl-2-deoxy-2-acetamido-β-D-glucopyranosyl azide 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: 86.0%

: 108-24-7
acetic anhydride

: 622830-65-3
O-(2,3,4-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-[O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->6)]-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide

: 622830-66-4
O-(2-deoxy-2-acetamido-β-D-glucopyranosyl)-(1->4)-[O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->6)]-3-O-benzyl-2-deoxy-2-acetamido-β-D-glucopyranosyl azide

Guidance literature:: O-(2,3,4-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-[O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->6)]-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide; With ethylenediamine; In butan-1-ol; at 90 ℃;

acetic anhydride; With pyridine; at 20 ℃;

With sodium methylate; In methanol; at 20 ℃; for 3h;
DOI:10.1021/jo034773s

Reference yield:

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

: 622830-66-4
O-(2-deoxy-2-acetamido-β-D-glucopyranosyl)-(1->4)-[O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->6)]-3-O-benzyl-2-deoxy-2-acetamido-β-D-glucopyranosyl azide

Guidance literature:: Multi-step reaction with 5 steps

1.1: aq. HBr; AcOH / CH₂Cl₂ / 4 h / 20 °C

2.1: 75 percent / AgOTf; 4 Angstroem molecular sieves / CH₂Cl₂ / -40 - 20 °C

3.1: 87 percent / TBAF; AcOH / tetrahydrofuran / 72 h / 0 - 20 °C

4.1: 85 percent / CuBr₂; 4 Angstroem molecular sieves; Bu₄NBr / CH₂Cl₂; dimethylformamide / 20 °C

5.1: ethylenediamine / butan-1-ol / 90 °C

5.2: pyridine / 20 °C

5.3: 86 percent / NaOMe / methanol / 3 h / 20 °C

With 4 A molecular sieve; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; hydrogen bromide; silver trifluoromethanesulfonate; acetic acid; ethylenediamine; copper(ll) bromide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; butan-1-ol;
DOI:10.1021/jo034773s

Reference yield:

: 70831-94-6
3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranosyl bromide

: 622830-66-4
O-(2-deoxy-2-acetamido-β-D-glucopyranosyl)-(1->4)-[O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->6)]-3-O-benzyl-2-deoxy-2-acetamido-β-D-glucopyranosyl azide

Guidance literature:: Multi-step reaction with 4 steps

1.1: 75 percent / AgOTf; 4 Angstroem molecular sieves / CH₂Cl₂ / -40 - 20 °C

2.1: 87 percent / TBAF; AcOH / tetrahydrofuran / 72 h / 0 - 20 °C

3.1: 85 percent / CuBr₂; 4 Angstroem molecular sieves; Bu₄NBr / CH₂Cl₂; dimethylformamide / 20 °C

4.1: ethylenediamine / butan-1-ol / 90 °C

4.2: pyridine / 20 °C

4.3: 86 percent / NaOMe / methanol / 3 h / 20 °C

With 4 A molecular sieve; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; silver trifluoromethanesulfonate; acetic acid; ethylenediamine; copper(ll) bromide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; butan-1-ol;
DOI:10.1021/jo034773s