3-azidopropyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside

Base Information

Chemical Name:3-azidopropyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside
CAS No.:595569-05-4
Molecular Formula:C₃₉H₅₀N₄O₁₅
Molecular Weight:814.844
Hs Code.:

Synonyms:3-azidopropyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside

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Chemical Property of 3-azidopropyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside

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Technology Process of 3-azidopropyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside

There total 5 articles about 3-azidopropyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-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: 76.0%

: 595569-03-2
3-azidopropyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside

: 3068-32-4
1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside

: 595569-05-4
3-azidopropyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside

Guidance literature:: With silver trifluoromethanesulfonate; In dichloromethane; at -30 - -10 ℃; for 3h;
DOI:10.1016/S0008-6215(03)00167-8

Reference yield:

: 94715-74-9
O-(2-Acetamido-3,4,6-tri-O-acetyl-2-desoxy-α-D-glucopyranosyl)trichloracetimidat

: 595569-05-4
3-azidopropyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 8 steps

1.1: 76 percent / Me₃SiOTf / CH₂Cl₂ / 1 h / -10 °C

2.1: 94 percent / NaN₃ / dimethylformamide / 3 h / 60 °C

3.1: 94 percent / NaOMe / methanol

4.1: 87 percent / p-TsOH / acetonitrile; dimethylformamide / 48 h / 25 °C

5.1: 84 percent / Bu₄NBr; aq. NaOH / CH₂Cl₂ / 48 h / 25 °C

6.1: 96 percent / aq. AcOH / 3 h / 80 °C

7.1: Bu₂SnO / toluene / 18 h / Heating

7.2: 52 percent / Bu₄NBr / toluene / 60 °C

8.1: 76 percent / AgOTF / CH₂Cl₂ / 3 h / -30 - -10 °C

With sodium hydroxide; sodium azide; trimethylsilyl trifluoromethanesulfonate; tetrabutylammomium bromide; sodium methylate; silver trifluoromethanesulfonate; di(n-butyl)tin oxide; toluene-4-sulfonic acid; acetic acid; In methanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1016/S0008-6215(03)00167-8

Reference yield:

: 595568-97-1
3-bromopropyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside

: 595569-05-4
3-azidopropyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1.1: 94 percent / NaN₃ / dimethylformamide / 3 h / 60 °C

2.1: 94 percent / NaOMe / methanol

3.1: 87 percent / p-TsOH / acetonitrile; dimethylformamide / 48 h / 25 °C

4.1: 84 percent / Bu₄NBr; aq. NaOH / CH₂Cl₂ / 48 h / 25 °C

5.1: 96 percent / aq. AcOH / 3 h / 80 °C

6.1: Bu₂SnO / toluene / 18 h / Heating

6.2: 52 percent / Bu₄NBr / toluene / 60 °C

7.1: 76 percent / AgOTF / CH₂Cl₂ / 3 h / -30 - -10 °C

With sodium hydroxide; sodium azide; tetrabutylammomium bromide; sodium methylate; silver trifluoromethanesulfonate; di(n-butyl)tin oxide; toluene-4-sulfonic acid; acetic acid; In methanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1016/S0008-6215(03)00167-8