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-3,6-di-O-acetyl-1-O-trichloroacetimidoyl-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-3,6-di-O-acetyl-1-O-trichloroacetimidoyl-β-D-glucopyranose
CAS No.:1374030-67-7
Molecular Formula:C₆₁H₆₄Cl₃N₇O₁₈
Molecular Weight:1289.57
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-3,6-di-O-acetyl-1-O-trichloroacetimidoyl-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-3,6-di-O-acetyl-1-O-trichloroacetimidoyl-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-3,6-di-O-acetyl-1-O-trichloroacetimidoyl-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-3,6-di-O-acetyl-1-O-trichloroacetimidoyl-β-D-glucopyranose

There total 17 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-3,6-di-O-acetyl-1-O-trichloroacetimidoyl-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: 78.0%

: 1374030-65-5
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-3,6-di-O-acetyl-β-D-glucopyranose

: 545-06-2
trichloroacetonitrile

: 1374030-67-7
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-3,6-di-O-acetyl-1-O-trichloroacetimidoyl-β-D-glucopyranose

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; Cooling;

Reference yield:

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

: 1374030-67-7
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-3,6-di-O-acetyl-1-O-trichloroacetimidoyl-β-D-glucopyranose

Guidance literature:: Multi-step reaction with 7 steps

1: boron trifluoride diethyl etherate / dichloromethane / -10 - 20 °C / Inert atmosphere; Large scale

2: hydrazinium monoacetate / N,N-dimethyl-formamide / -10 - 20 °C / Large scale

3: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 20 °C / Inert atmosphere; Cooling; Large scale

4: triethylsilyl trifluoromethyl sulfonate / dichloromethane / 2 h / -40 - 20 °C / Inert atmosphere; Cooling

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

6: benzylamine / tetrahydrofuran / 4 h / 5 - 15 °C

7: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / Cooling

With boron trifluoride diethyl etherate; triethylsilyl trifluoromethyl sulfonate; hydrazinium monoacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; benzylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

Reference yield:

: 2873-29-2
D-glucal triacetate

: 1374030-67-7
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-3,6-di-O-acetyl-1-O-trichloroacetimidoyl-β-D-glucopyranose

Guidance literature:: Multi-step reaction with 12 steps

1.1: sodium methylate / methanol / 2 h

2.1: bis(tri-n-butyltin)oxide / acetonitrile / 16 h / Molecular sieve

2.2: 3.25 h / 5 - 20 °C / Inert atmosphere

3.1: sodium hydride / N,N-dimethyl-formamide / 3 h / -20 - 20 °C

4.1: sodium azide / N,N-dimethyl-formamide; water / 12 h / 120 °C

5.1: sodium hydride / N,N-dimethyl-formamide / 3 h / 0 - 20 °C

6.1: boron trifluoride diethyl etherate / dichloromethane / -10 - 20 °C / Inert atmosphere; Large scale

7.1: hydrazinium monoacetate / N,N-dimethyl-formamide / -10 - 20 °C / Large scale

8.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 20 °C / Inert atmosphere; Cooling; Large scale

9.1: triethylsilyl trifluoromethyl sulfonate / dichloromethane / 2 h / -40 - 20 °C / Inert atmosphere; Cooling

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

11.1: benzylamine / tetrahydrofuran / 4 h / 5 - 15 °C

12.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / Cooling

With sodium azide; boron trifluoride diethyl etherate; triethylsilyl trifluoromethyl sulfonate; sodium methylate; hydrazinium monoacetate; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; benzylamine; bis(tri-n-butyltin)oxide; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;