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

Base Information

Chemical Name:methyl 4-O-[2-azido-4-O-benzyl-2-deoxy-3-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-3-O-benzyl-β-D-glucopyranosiduronic acid
CAS No.:1415973-67-9
Molecular Formula:C₃₈H₄₁N₃O₁₁
Molecular Weight:715.757
Hs Code.:

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

There total 11 articles about methyl 4-O-[2-azido-4-O-benzyl-2-deoxy-3-O-(2-naphthylmethyl)-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: 97.0%

: 1415974-59-2
methyl 4-O-[2-azido-4-O-benzyl-2-deoxy-3-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-β-D-glucopyranosiduronic acid

: 1415973-67-9
methyl 4-O-[2-azido-4-O-benzyl-2-deoxy-3-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-3-O-benzyl-β-D-glucopyranosiduronic acid

Guidance literature:: With sodium methylate; In methanol; dichloromethane; at 20 ℃; for 6h; chemoselective reaction; Inert atmosphere;
DOI:10.1021/ja3090065

Reference yield:

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

: 1415973-67-9
methyl 4-O-[2-azido-4-O-benzyl-2-deoxy-3-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-3-O-benzyl-β-D-glucopyranosiduronic acid

Guidance literature:: Multi-step reaction with 7 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: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 70 h / 40 °C

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

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; In tetrahydrofuran; methanol; dichloromethane; water;
DOI:10.1021/ja3090065

Reference yield:

: 942043-17-6
4-methylphenyl 2,3,4,6-tetrakis-O-trimethylsilyl-1-thio-β-D-glucopyranoside

: 1415973-67-9
methyl 4-O-[2-azido-4-O-benzyl-2-deoxy-3-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-3-O-benzyl-β-D-glucopyranosiduronic acid

Guidance literature:: Multi-step reaction with 11 steps

1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h / 0 °C / Inert atmosphere; Molecular sieve

2: trimethylsilyl trifluoromethanesulfonate; triethylsilane / dichloromethane / 4 h / -78 °C / Inert atmosphere; Molecular sieve

3: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 18 h / 0 °C / Inert atmosphere; Molecular sieve

4: trifluoroacetic acid; water / dichloromethane / 3 h / 20 °C / Inert atmosphere; Molecular sieve

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

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

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

8: magnesium methanolate / methanol; dichloromethane / 2 h

9: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane; water / 6 h / 20 °C

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

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

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