6-O-acetyl-2-azido-2-deoxy-3,4-di-O-benzyl-α-D-glucopyranosyl-(1->4)-O-[benzyl 3-O-benzyl-2-O-levulinoyl-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 3-O-benzyl-2-O-levulinoyl-β-D-glucopyranosyluronate]-(1->4)-O-2-azido-2-deoxy-1,3,6-tri-O-acetyl-β-D-glucopyranose
• CAS No.: 1262887-53-5
• Molecular Formula: C₅₉H₆₆N₆O₂₁
• Molecular Weight: 1195.2

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 19 articles about 6-O-acetyl-2-azido-2-deoxy-3,4-di-O-benzyl-α-D-glucopyranosyl-(1->4)-O-[benzyl 3-O-benzyl-2-O-levulinoyl-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:

1,6-anhydro-2-azido-3,4-di-O-benzyl-2-deoxy-D-glucopyranose (55682-48-9) → 6-O-acetyl-2-azido-2-deoxy-3,4-di-O-benzyl-α-D-glucopyranosyl-(1->4)-O-[benzyl 3-O-benzyl-2-O-levulinoyl-β-D-glucopyranosyluronate]-(1->4)-O-2-azido-2-deoxy-1,3,6-tri-O-acetyl-β-D-glucopyranose (1262887-53-5)

Guidance literature:

Multi-step reaction with 11 steps

1: boron trifluoride diethyl etherate / dichloromethane / 3 h / -10 - 20 °C / Industry scale; Inert atmosphere

2: hydrazinium monoacetate / N,N-dimethyl-formamide / 3 h / 20 °C / Industry scale

3: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 2 h / 20 °C / Inert atmosphere; Industry scale

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

5: trifluoroacetic acid / 4 h / -5 - 20 °C / Industry scale

6: 1H-imidazole / dichloromethane / -20 - 20 °C / Inert atmosphere; Industry scale

7: dmap; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 16 h / 10 - 20 °C / Inert atmosphere; Industry scale

8: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 3 h / 0 - 20 °C / Industry scale

9: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 2 h / 20 °C / Inert atmosphere; Industry scale

10: triethylsilyl trifluoromethyl sulfonate / dichloromethane / 2 h / -20 - 5 °C / Industry scale; Inert atmosphere

11: boron trifluoride diethyl etherate / dichloromethane / 3 h / -45 - 10 °C / Industry scale; Inert atmosphere

With 1H-imidazole; dmap; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; triethylsilyl trifluoromethyl sulfonate; hydrazinium monoacetate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

Reference yield:

6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl-(1->4)-benzyl (3-O-benzyl-2-O-levulinoyl)-β-D-glucopyranosyluronate-(1->4)-(3-O-acetyl-1,6-anhydro-2-azido)-2-deoxy-β-D-glucopyranose (1262887-52-4) + acetic anhydride (108-24-7) → 6-O-acetyl-2-azido-2-deoxy-3,4-di-O-benzyl-α-D-glucopyranosyl-(1->4)-O-[benzyl 3-O-benzyl-2-O-levulinoyl-β-D-glucopyranosyluronate]-(1->4)-O-2-azido-2-deoxy-1,3,6-tri-O-acetyl-β-D-glucopyranose (1262887-53-5)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -45 - 10 ℃; for 3h; Industry scale; Inert atmosphere;

Reference yield:

β-D-glucose pentaacetate (604-69-3) → 6-O-acetyl-2-azido-2-deoxy-3,4-di-O-benzyl-α-D-glucopyranosyl-(1->4)-O-[benzyl 3-O-benzyl-2-O-levulinoyl-β-D-glucopyranosyluronate]-(1->4)-O-2-azido-2-deoxy-1,3,6-tri-O-acetyl-β-D-glucopyranose (1262887-53-5)

Guidance literature:

Multi-step reaction with 16 steps

1.1: hydrogen bromide; acetic acid / dichloromethane / 3 h / 0 - 20 °C

2.1: tetra-(n-butyl)ammonium iodide; sodium tetrahydroborate / acetonitrile / 16 h / 40 °C / Molecular sieve

3.1: sodium methylate / methanol / 3 h / 50 °C

4.1: (1S)-10-camphorsulfonic acid / 2 h / 50 °C

5.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C

5.2: 0.5 h

6.1: trifluoroacetic acid; water / dichloromethane / 0 °C

7.1: tetrabutyl-ammonium chloride; sodium hydrogencarbonate; sodium hypochlorite; sodium bromide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / ethyl acetate / 16 h / 20 °C

8.1: triethylamine; dicyclohexyl-carbodiimide; benzotriazol-1-ol / dichloromethane / 16 h / 20 °C

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

10.1: trifluoroacetic acid / 4 h / -5 - 20 °C / Industry scale

11.1: 1H-imidazole / dichloromethane / -20 - 20 °C / Inert atmosphere; Industry scale

12.1: dmap; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 16 h / 10 - 20 °C / Inert atmosphere; Industry scale

13.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 3 h / 0 - 20 °C / Industry scale

14.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 2 h / 20 °C / Inert atmosphere; Industry scale

15.1: triethylsilyl trifluoromethyl sulfonate / dichloromethane / 2 h / -20 - 5 °C / Industry scale; Inert atmosphere

16.1: boron trifluoride diethyl etherate / dichloromethane / 3 h / -45 - 10 °C / Industry scale; Inert atmosphere

With 1H-imidazole; dmap; sodium hypochlorite; sodium tetrahydroborate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; boron trifluoride diethyl etherate; (1S)-10-camphorsulfonic acid; tetrabutyl ammonium fluoride; tetrabutyl-ammonium chloride; water; hydrogen bromide; triethylsilyl trifluoromethyl sulfonate; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium hydrogencarbonate; benzotriazol-1-ol; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; sodium bromide; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; acetonitrile;

upstream raw materials:

β-D-glucose pentaacetate

6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl-(1->4)-benzyl (3-O-benzyl-2-O-levulinoyl)-β-D-glucopyranosyluronate-(1->4)-(3-O-acetyl-1,6-anhydro-2-azido)-2-deoxy-β-D-glucopyranose

acetic anhydride

1,6-di-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranose

Downstream raw materials:

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

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