methyl 4-O-(2-azido-4-O-benzyl-2-deoxy-α-D-glucopyranosyl)-3-O-benzyl-β-D-glucopyranosiduronic acid

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Chemical Name:methyl 4-O-(2-azido-4-O-benzyl-2-deoxy-α-D-glucopyranosyl)-3-O-benzyl-β-D-glucopyranosiduronic acid
CAS No.:1415974-85-4
Molecular Formula:C₂₇H₃₃N₃O₁₁
Molecular Weight:575.573
Hs Code.:

Synonyms:methyl 4-O-(2-azido-4-O-benzyl-2-deoxy-α-D-glucopyranosyl)-3-O-benzyl-β-D-glucopyranosiduronic acid

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Chemical Property of methyl 4-O-(2-azido-4-O-benzyl-2-deoxy-α-D-glucopyranosyl)-3-O-benzyl-β-D-glucopyranosiduronic acid

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Technology Process of methyl 4-O-(2-azido-4-O-benzyl-2-deoxy-α-D-glucopyranosyl)-3-O-benzyl-β-D-glucopyranosiduronic acid

There total 12 articles about methyl 4-O-(2-azido-4-O-benzyl-2-deoxy-α-D-glucopyranosyl)-3-O-benzyl-β-D-glucopyranosiduronic acid 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: 92.0%

: 1415974-82-1
methyl 4-O-(2-azido-4-O-benzyl-6-O-(tert-butyldiphenylsilyl)-2-deoxy-α-D-glucopyranosyl)-3-O-benzyl-β-D-glucopyranosiduronic acid

: 1415974-85-4
methyl 4-O-(2-azido-4-O-benzyl-2-deoxy-α-D-glucopyranosyl)-3-O-benzyl-β-D-glucopyranosiduronic acid

Guidance literature:: With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; at 40 ℃; for 70h; chemoselective reaction;
DOI:10.1021/ja3090065

Reference yield:

: 1415974-78-5
methyl 4-O-[2-azido-4-O-benzyl-6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-3-O-benzyl-β-D-glucopyranosiduronic acid

: 1415974-85-4
methyl 4-O-(2-azido-4-O-benzyl-2-deoxy-α-D-glucopyranosyl)-3-O-benzyl-β-D-glucopyranosiduronic acid

Guidance literature:: Multi-step reaction with 2 steps

1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 4 h / 20 °C

2: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 70 h / 40 °C

With tetrabutyl ammonium fluoride; acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; water;
DOI:10.1021/ja3090065

Reference yield:

: 918948-16-0
p-methylphenyl 2-O-benzoyl-3-O-benzyl-1-thio-β-D-glucopyranoside

: 1415974-85-4
methyl 4-O-(2-azido-4-O-benzyl-2-deoxy-α-D-glucopyranosyl)-3-O-benzyl-β-D-glucopyranosiduronic acid

Guidance literature:: Multi-step reaction with 8 steps

1: triethylamine / dichloromethane / 3 h / 0 °C / Inert atmosphere

2: trimethylsilyl trifluoromethanesulfonate; N-iodo-succinimide / dichloromethane / 2 h / -78 - -20 °C / Inert atmosphere; Molecular sieve

3: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 3 h / -78 - -20 °C / Inert atmosphere; Molecular sieve

4: magnesium methanolate / methanol; dichloromethane / 2 h

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

6: sodium methylate / methanol; dichloromethane / 6 h / 20 °C / Inert atmosphere

7: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 4 h / 20 °C

8: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 70 h / 40 °C

With N-iodo-succinimide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; trimethylsilyl trifluoromethanesulfonate; [bis(acetoxy)iodo]benzene; tetrabutyl ammonium fluoride; sodium methylate; magnesium methanolate; acetic acid; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; dichloromethane; water;
DOI:10.1021/ja3090065