methyl 4-O-[2-azido-4-O-benzyl-2-deoxy-3-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-3-O-benzyl-α-L-idopyranosidurono-6,2-lactone

Base Information

Chemical Name:methyl 4-O-[2-azido-4-O-benzyl-2-deoxy-3-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-3-O-benzyl-α-L-idopyranosidurono-6,2-lactone
CAS No.:1415974-09-2
Molecular Formula:C₃₈H₃₉N₃O₁₀
Molecular Weight:697.742
Hs Code.:

Synonyms:methyl 4-O-[2-azido-4-O-benzyl-2-deoxy-3-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-3-O-benzyl-α-L-idopyranosidurono-6,2-lactone

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Chemical Property of methyl 4-O-[2-azido-4-O-benzyl-2-deoxy-3-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-3-O-benzyl-α-L-idopyranosidurono-6,2-lactone

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Technology Process of methyl 4-O-[2-azido-4-O-benzyl-2-deoxy-3-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-3-O-benzyl-α-L-idopyranosidurono-6,2-lactone

There total 6 articles about methyl 4-O-[2-azido-4-O-benzyl-2-deoxy-3-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-3-O-benzyl-α-L-idopyranosidurono-6,2-lactone 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: 88.0%

: 1415973-65-7
methyl 4-O-[2-azido-4-O-benzyl-6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-3-O-benzyl-α-L-idopyranosidurono-6,2-lactone

: 1415974-09-2
methyl 4-O-[2-azido-4-O-benzyl-2-deoxy-3-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-3-O-benzyl-α-L-idopyranosidurono-6,2-lactone

Guidance literature:: With tris(dimethylamino)sulfonium trimethylsilyldifluoride; In N,N-dimethyl-formamide; at 20 ℃; for 16h;
DOI:10.1021/ja3090065

Reference yield:

: 1415974-54-7
6-O-acetyl-4-O-[2-azido-4-O-benzyl-6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-L-idopyranosyl acetate

: 1415974-09-2
methyl 4-O-[2-azido-4-O-benzyl-2-deoxy-3-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-3-O-benzyl-α-L-idopyranosidurono-6,2-lactone

Guidance literature:: Multi-step reaction with 6 steps

1: ammonia / methanol; tetrahydrofuran / 3.05 h / 0 °C

2: potassium carbonate / dichloromethane / 16 h / 20 °C / Inert atmosphere

3: silver trifluoromethanesulfonate / dichloromethane / 1 h / -5 °C / Inert atmosphere; Molecular sieve

4: sodium methylate / methanol; dichloromethane / 20 °C / Inert atmosphere

5: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane; water / 6 h / 20 °C

6: tris(dimethylamino)sulfonium trimethylsilyldifluoride / N,N-dimethyl-formamide / 16 h / 20 °C

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; tris(dimethylamino)sulfonium trimethylsilyldifluoride; ammonia; sodium methylate; silver trifluoromethanesulfonate; potassium carbonate; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/ja3090065

Reference yield:

: 6-O-acetyl-4-O-[2-azido-4-O-benzyl-6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-L-idopyranose

: 1415974-09-2
methyl 4-O-[2-azido-4-O-benzyl-2-deoxy-3-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-3-O-benzyl-α-L-idopyranosidurono-6,2-lactone

Guidance literature:: Multi-step reaction with 5 steps

1: potassium carbonate / dichloromethane / 16 h / 20 °C / Inert atmosphere

2: silver trifluoromethanesulfonate / dichloromethane / 1 h / -5 °C / Inert atmosphere; Molecular sieve

3: sodium methylate / methanol; dichloromethane / 20 °C / Inert atmosphere

4: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane; water / 6 h / 20 °C

5: tris(dimethylamino)sulfonium trimethylsilyldifluoride / N,N-dimethyl-formamide / 16 h / 20 °C

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; tris(dimethylamino)sulfonium trimethylsilyldifluoride; sodium methylate; silver trifluoromethanesulfonate; potassium carbonate; In methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/ja3090065