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

Base Information

Chemical Name:methyl 4-O-(2-azido-4-O-benzyl-6-O-(tert-butyldiphenylsilyl)-2-deoxy-α-D-glucopyranosyl)-2-O-benzoyl-3-O-benzyl-β-D-glucopyranosiduronic acid
CAS No.:1415974-61-6
Molecular Formula:C₅₀H₅₅N₃O₁₂Si
Molecular Weight:918.085
Hs Code.:

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

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Chemical Property of methyl 4-O-(2-azido-4-O-benzyl-6-O-(tert-butyldiphenylsilyl)-2-deoxy-α-D-glucopyranosyl)-2-O-benzoyl-3-O-benzyl-β-D-glucopyranosiduronic acid

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Technology Process of methyl 4-O-(2-azido-4-O-benzyl-6-O-(tert-butyldiphenylsilyl)-2-deoxy-α-D-glucopyranosyl)-2-O-benzoyl-3-O-benzyl-β-D-glucopyranosiduronic acid

There total 10 articles about methyl 4-O-(2-azido-4-O-benzyl-6-O-(tert-butyldiphenylsilyl)-2-deoxy-α-D-glucopyranosyl)-2-O-benzoyl-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: 95.0%

: 1415973-64-6
methyl 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-β-D-glucopyranosiduronic acid

: 1415974-61-6
methyl 4-O-(2-azido-4-O-benzyl-6-O-(tert-butyldiphenylsilyl)-2-deoxy-α-D-glucopyranosyl)-2-O-benzoyl-3-O-benzyl-β-D-glucopyranosiduronic acid

Guidance literature:: With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; at 20 ℃; for 4h; chemoselective reaction;
DOI:10.1021/ja3090065

Reference yield:

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

: 1415974-61-6
methyl 4-O-(2-azido-4-O-benzyl-6-O-(tert-butyldiphenylsilyl)-2-deoxy-α-D-glucopyranosyl)-2-O-benzoyl-3-O-benzyl-β-D-glucopyranosiduronic acid

Guidance literature:: Multi-step reaction with 6 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: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 4 h / 20 °C

With N-iodo-succinimide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; trimethylsilyl trifluoromethanesulfonate; [bis(acetoxy)iodo]benzene; magnesium methanolate; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 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

: 1415974-61-6
methyl 4-O-(2-azido-4-O-benzyl-6-O-(tert-butyldiphenylsilyl)-2-deoxy-α-D-glucopyranosyl)-2-O-benzoyl-3-O-benzyl-β-D-glucopyranosiduronic acid

Guidance literature:: Multi-step reaction with 10 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: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 4 h / 20 °C

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