methyl 2,3,4-tri-O-benzoyl-β-D-glucopyranosyluronate-(1→4)-2-azido-2-deoxy-3-O-benzyl-6-O-benzyl-α-D-glucopyranoside

Base Information

Chemical Name:methyl 2,3,4-tri-O-benzoyl-β-D-glucopyranosyluronate-(1→4)-2-azido-2-deoxy-3-O-benzyl-6-O-benzyl-α-D-glucopyranoside
CAS No.:1582775-53-8
Molecular Formula:C₄₈H₄₅N₃O₁₄
Molecular Weight:887.897
Hs Code.:

Synonyms:methyl 2,3,4-tri-O-benzoyl-β-D-glucopyranosyluronate-(1→4)-2-azido-2-deoxy-3-O-benzyl-6-O-benzyl-α-D-glucopyranoside

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Chemical Property of methyl 2,3,4-tri-O-benzoyl-β-D-glucopyranosyluronate-(1→4)-2-azido-2-deoxy-3-O-benzyl-6-O-benzyl-α-D-glucopyranoside

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Technology Process of methyl 2,3,4-tri-O-benzoyl-β-D-glucopyranosyluronate-(1→4)-2-azido-2-deoxy-3-O-benzyl-6-O-benzyl-α-D-glucopyranoside

There total 15 articles about methyl 2,3,4-tri-O-benzoyl-β-D-glucopyranosyluronate-(1→4)-2-azido-2-deoxy-3-O-benzyl-6-O-benzyl-α-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: 89.0%

: 1582775-49-2
methyl 2,3,4-tri-O-benzoyl-β-D-glucopyranosyl-(1→4)-2-azido-2-deoxy-3-O-benzyl-6-O-benzyl-α-D-glucopyranoside

: 1582775-53-8
methyl 2,3,4-tri-O-benzoyl-β-D-glucopyranosyluronate-(1→4)-2-azido-2-deoxy-3-O-benzyl-6-O-benzyl-α-D-glucopyranoside

Guidance literature:: With 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene; In dichloromethane; water; at 20 ℃;
DOI:10.1021/ol500738g

Reference yield:

: methyl 2-azido-2-deoxy-4,6-O-benzylidene-D-glucopyranoside

: 1582775-53-8
methyl 2,3,4-tri-O-benzoyl-β-D-glucopyranosyluronate-(1→4)-2-azido-2-deoxy-3-O-benzyl-6-O-benzyl-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1.1: pyridine; dmap / 0 - 20 °C / Inert atmosphere

2.1: sodium methylate / methanol / 0 - 20 °C / Inert atmosphere

3.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 20 °C / Inert atmosphere

3.2: 20 °C / Inert atmosphere

4.1: boron trifluoride diethyl etherate; triethylsilane / dichloromethane / 2 h / 0 °C / Inert atmosphere

5.1: dichloromethane / 0.5 h / 20 °C / Molecular sieve; Inert atmosphere

5.2: 2 h / 0 - 20 °C / Inert atmosphere

6.1: pyridine; hydrogen fluoride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

7.1: 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene / dichloromethane; water / 20 °C

With pyridine; triethylsilane; dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene; boron trifluoride diethyl etherate; hydrogen fluoride; sodium methylate; sodium hydride; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/ol500738g

Reference yield:

: 273749-59-0
methyl 2-azido-2-deoxy-α/β-D-glucopyranoside

: 1582775-53-8
methyl 2,3,4-tri-O-benzoyl-β-D-glucopyranosyluronate-(1→4)-2-azido-2-deoxy-3-O-benzyl-6-O-benzyl-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 8 steps

1.1: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

2.1: pyridine; dmap / 0 - 20 °C / Inert atmosphere

3.1: sodium methylate / methanol / 0 - 20 °C / Inert atmosphere

4.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 20 °C / Inert atmosphere

4.2: 20 °C / Inert atmosphere

5.1: boron trifluoride diethyl etherate; triethylsilane / dichloromethane / 2 h / 0 °C / Inert atmosphere

6.1: dichloromethane / 0.5 h / 20 °C / Molecular sieve; Inert atmosphere

6.2: 2 h / 0 - 20 °C / Inert atmosphere

7.1: pyridine; hydrogen fluoride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

8.1: 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene / dichloromethane; water / 20 °C

With pyridine; triethylsilane; dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene; boron trifluoride diethyl etherate; hydrogen fluoride; sodium methylate; sodium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/ol500738g