methyl 4-O-[2-acetamido-4-O-benzyl-6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-3-O-benzyl-α-L-idopyranosiduronic acid

Base Information

Chemical Name:methyl 4-O-[2-acetamido-4-O-benzyl-6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-3-O-benzyl-α-L-idopyranosiduronic acid
CAS No.:1415975-09-5
Molecular Formula:C₅₆H₆₃NO₁₂Si
Molecular Weight:970.201
Hs Code.:

methyl 4-O-[2-acetamido-4-O-benzyl-6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-3-O-benzyl-α-L-idopyranosiduronic acid

Synonyms:methyl 4-O-[2-acetamido-4-O-benzyl-6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-3-O-benzyl-α-L-idopyranosiduronic acid

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Chemical Property of methyl 4-O-[2-acetamido-4-O-benzyl-6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-3-O-benzyl-α-L-idopyranosiduronic acid

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Technology Process of methyl 4-O-[2-acetamido-4-O-benzyl-6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-3-O-benzyl-α-L-idopyranosiduronic acid

There total 7 articles about methyl 4-O-[2-acetamido-4-O-benzyl-6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-3-O-benzyl-α-L-idopyranosiduronic 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%

: 1415974-08-1
methyl 4-O-[2-acetamido-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

: 1415975-09-5
methyl 4-O-[2-acetamido-4-O-benzyl-6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-3-O-benzyl-α-L-idopyranosiduronic acid

Guidance literature:: With lithium hydroxide; In tetrahydrofuran; water; at 20 ℃; for 1h;
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

: 1415975-09-5
methyl 4-O-[2-acetamido-4-O-benzyl-6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-3-O-benzyl-α-L-idopyranosiduronic acid

Guidance literature:: Multi-step reaction with 7 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: pyridine / chloroform / 1.5 h / 20 °C / Inert atmosphere

7: lithium hydroxide / tetrahydrofuran; water / 1 h / 20 °C

With pyridine; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; ammonia; sodium methylate; silver trifluoromethanesulfonate; potassium carbonate; lithium hydroxide; In tetrahydrofuran; methanol; dichloromethane; chloroform; water;
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

: 1415975-09-5
methyl 4-O-[2-acetamido-4-O-benzyl-6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-3-O-benzyl-α-L-idopyranosiduronic acid

Guidance literature:: Multi-step reaction with 6 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: pyridine / chloroform / 1.5 h / 20 °C / Inert atmosphere

6: lithium hydroxide / tetrahydrofuran; water / 1 h / 20 °C

With pyridine; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; sodium methylate; silver trifluoromethanesulfonate; potassium carbonate; lithium hydroxide; In tetrahydrofuran; methanol; dichloromethane; chloroform; water;
DOI:10.1021/ja3090065