6-O-acetyl-2-azido-2-deoxy-3,4-di-O-benzyl-α-D-glucopyranosyl-(1→4)-O-[benzyl 2,3-O-dibenzyl-β-D-glucopyranosyluronate]-(1→4)-O-2-azido-2-deoxy-1,3,6-tri-O-acetyl-β-D-glucopyranose

Base Information

Chemical Name:6-O-acetyl-2-azido-2-deoxy-3,4-di-O-benzyl-α-D-glucopyranosyl-(1→4)-O-[benzyl 2,3-O-dibenzyl-β-D-glucopyranosyluronate]-(1→4)-O-2-azido-2-deoxy-1,3,6-tri-O-acetyl-β-D-glucopyranose
CAS No.:1374030-63-3
Molecular Formula:C₆₁H₆₆N₆O₁₉
Molecular Weight:1187.22
Hs Code.:

6-O-acetyl-2-azido-2-deoxy-3,4-di-O-benzyl-α-D-glucopyranosyl-(1→4)-O-[benzyl 2,3-O-dibenzyl-β-D-glucopyranosyluronate]-(1→4)-O-2-azido-2-deoxy-1,3,6-tri-O-acetyl-β-D-glucopyranose

Synonyms:6-O-acetyl-2-azido-2-deoxy-3,4-di-O-benzyl-α-D-glucopyranosyl-(1→4)-O-[benzyl 2,3-O-dibenzyl-β-D-glucopyranosyluronate]-(1→4)-O-2-azido-2-deoxy-1,3,6-tri-O-acetyl-β-D-glucopyranose

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Chemical Property of 6-O-acetyl-2-azido-2-deoxy-3,4-di-O-benzyl-α-D-glucopyranosyl-(1→4)-O-[benzyl 2,3-O-dibenzyl-β-D-glucopyranosyluronate]-(1→4)-O-2-azido-2-deoxy-1,3,6-tri-O-acetyl-β-D-glucopyranose

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Technology Process of 6-O-acetyl-2-azido-2-deoxy-3,4-di-O-benzyl-α-D-glucopyranosyl-(1→4)-O-[benzyl 2,3-O-dibenzyl-β-D-glucopyranosyluronate]-(1→4)-O-2-azido-2-deoxy-1,3,6-tri-O-acetyl-β-D-glucopyranose

There total 18 articles about 6-O-acetyl-2-azido-2-deoxy-3,4-di-O-benzyl-α-D-glucopyranosyl-(1→4)-O-[benzyl 2,3-O-dibenzyl-β-D-glucopyranosyluronate]-(1→4)-O-2-azido-2-deoxy-1,3,6-tri-O-acetyl-β-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: 65.0%

: 1374030-61-1
EDC-Trimer-CB

: 108-24-7
acetic anhydride

: 1374030-63-3
6-O-acetyl-2-azido-2-deoxy-3,4-di-O-benzyl-α-D-glucopyranosyl-(1→4)-O-[benzyl 2,3-O-dibenzyl-β-D-glucopyranosyluronate]-(1→4)-O-2-azido-2-deoxy-1,3,6-tri-O-acetyl-β-D-glucopyranose

Guidance literature:: With boron trifluoride diethyl etherate; In dichloromethane; at -45 - 20 ℃; for 6h;

Reference yield:

: 55682-48-9
1,6-anhydro-2-azido-3,4-di-O-benzyl-2-deoxy-D-glucopyranose

: 1374030-63-3
6-O-acetyl-2-azido-2-deoxy-3,4-di-O-benzyl-α-D-glucopyranosyl-(1→4)-O-[benzyl 2,3-O-dibenzyl-β-D-glucopyranosyluronate]-(1→4)-O-2-azido-2-deoxy-1,3,6-tri-O-acetyl-β-D-glucopyranose

Guidance literature:: Multi-step reaction with 5 steps

1.1: boron trifluoride diethyl etherate / dichloromethane / -10 - 20 °C / Inert atmosphere

2.1: hydrazinium monoacetate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 20 °C / Inert atmosphere

4.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h / -40 - 20 °C / Inert atmosphere

4.2: 0.5 h

5.1: boron trifluoride diethyl etherate / dichloromethane / 6 h / -45 - 20 °C

With trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; hydrazinium monoacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; N,N-dimethyl-formamide;

Reference yield:

: 99541-24-9
O-(2,3-di-O-benzyl-β-D-glucopyranosyl)-(1->4)-3-O-acetyl-1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose

: 1374030-63-3
6-O-acetyl-2-azido-2-deoxy-3,4-di-O-benzyl-α-D-glucopyranosyl-(1→4)-O-[benzyl 2,3-O-dibenzyl-β-D-glucopyranosyluronate]-(1→4)-O-2-azido-2-deoxy-1,3,6-tri-O-acetyl-β-D-glucopyranose

Guidance literature:: Multi-step reaction with 4 steps

1.1: sodium hypochlorite / 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / acetonitrile / 35 °C / pH 6.5 / Aqueous phosphate buffer

2.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dmap / dichloromethane / 16 h / 20 °C / Inert atmosphere

3.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h / -40 - 20 °C / Inert atmosphere

3.2: 0.5 h

4.1: boron trifluoride diethyl etherate / dichloromethane / 6 h / -45 - 20 °C

With sodium hypochlorite; trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; In dichloromethane; acetonitrile;