1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-4-O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-β-D-glucopyranose

Base Information

Chemical Name:1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-4-O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-β-D-glucopyranose
CAS No.:796873-40-0
Molecular Formula:C₂₆H₃₁N₃O₁₃
Molecular Weight:593.544
Hs Code.:

Synonyms:1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-4-O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-β-D-glucopyranose

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Chemical Property of 1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-4-O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-β-D-glucopyranose

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Technology Process of 1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-4-O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-β-D-glucopyranose

There total 7 articles about 1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-4-O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-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: 1.68%

: 108-24-7
acetic anhydride

: 1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-4-O-(methyl β-D-glucopyranosyluronate)-β-D-glucopyranose

: 796873-40-0
1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-4-O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-β-D-glucopyranose

Guidance literature:: With dmap; In N,N-dimethyl-formamide; at 20 ℃; for 12h;
DOI:10.1016/j.carres.2004.07.018

Reference yield:

: 104707-00-8
methyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-glucopyranoside

: 796873-40-0
1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-4-O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-β-D-glucopyranose

Guidance literature:: Multi-step reaction with 5 steps

1: 74 percent / N-idosuccinimide; silver triflate / CH₂Cl₂

2: 100 percent / NaOMe / methanol; tetrahydrofuran / 48 h / 20 °C

3: KBr; 1,2,6,6-tetramethylpiperidine-1-oxide; NaOCl / aq. NaHCO₃; tetrahydrofuran / 0.5 h / 20 °C

4: dimethylformamide / 12 h

5: 1.68 percent / DMAP / dimethylformamide / 12 h / 20 °C

With dmap; sodium hypochlorite; N-iodo-succinimide; 1,2,6,6-tetramethylpiperidine-1-oxide; sodium methylate; silver trifluoromethanesulfonate; potassium bromide; In tetrahydrofuran; methanol; dichloromethane; sodium hydrogencarbonate; N,N-dimethyl-formamide;
DOI:10.1016/j.carres.2004.07.018

Reference yield:

: 55682-57-0
1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose

: 796873-40-0
1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-4-O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-β-D-glucopyranose

Guidance literature:: Multi-step reaction with 5 steps

1: 74 percent / N-idosuccinimide; silver triflate / CH₂Cl₂

2: 100 percent / NaOMe / methanol; tetrahydrofuran / 48 h / 20 °C

3: KBr; 1,2,6,6-tetramethylpiperidine-1-oxide; NaOCl / aq. NaHCO₃; tetrahydrofuran / 0.5 h / 20 °C

4: dimethylformamide / 12 h

5: 1.68 percent / DMAP / dimethylformamide / 12 h / 20 °C

With dmap; sodium hypochlorite; N-iodo-succinimide; 1,2,6,6-tetramethylpiperidine-1-oxide; sodium methylate; silver trifluoromethanesulfonate; potassium bromide; In tetrahydrofuran; methanol; dichloromethane; sodium hydrogencarbonate; N,N-dimethyl-formamide;
DOI:10.1016/j.carres.2004.07.018