methyl (4'-methoxybenzyl-5-acetamido-4,7,8,9-tetra-O-acetyl-5-deoxy-3-O-acetonitrile-D-erythro-α-L-gluco-non-2-ulopyranoside)onate

Base Information

Chemical Name:methyl (4'-methoxybenzyl-5-acetamido-4,7,8,9-tetra-O-acetyl-5-deoxy-3-O-acetonitrile-D-erythro-α-L-gluco-non-2-ulopyranoside)onate
CAS No.:1262101-67-6
Molecular Formula:C₃₀H₃₈N₂O₁₅
Molecular Weight:666.636
Hs Code.:

Synonyms:methyl (4'-methoxybenzyl-5-acetamido-4,7,8,9-tetra-O-acetyl-5-deoxy-3-O-acetonitrile-D-erythro-α-L-gluco-non-2-ulopyranoside)onate

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Chemical Property of methyl (4'-methoxybenzyl-5-acetamido-4,7,8,9-tetra-O-acetyl-5-deoxy-3-O-acetonitrile-D-erythro-α-L-gluco-non-2-ulopyranoside)onate

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Technology Process of methyl (4'-methoxybenzyl-5-acetamido-4,7,8,9-tetra-O-acetyl-5-deoxy-3-O-acetonitrile-D-erythro-α-L-gluco-non-2-ulopyranoside)onate

There total 6 articles about methyl (4'-methoxybenzyl-5-acetamido-4,7,8,9-tetra-O-acetyl-5-deoxy-3-O-acetonitrile-D-erythro-α-L-gluco-non-2-ulopyranoside)onate 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: 81.0%

: 1262101-60-9
methyl (4'-methoxybenzyl-5-acetamido-4,7,8,9-tetra-O-acetyl-5-dideoxy-D-erythro-α-L-gluco-non-2-ulopyranoside)onate

: 590-17-0
cyanomethyl bromide

: 1262101-67-6
methyl (4'-methoxybenzyl-5-acetamido-4,7,8,9-tetra-O-acetyl-5-deoxy-3-O-acetonitrile-D-erythro-α-L-gluco-non-2-ulopyranoside)onate

Guidance literature:: methyl (4'-methoxybenzyl-5-acetamido-4,7,8,9-tetra-O-acetyl-5-dideoxy-D-erythro-α-L-gluco-non-2-ulopyranoside)onate; cyanomethyl bromide; In dichloromethane; at 20 ℃; for 1h; Inert atmosphere; Molecular sieve;

With tetra-(n-butyl)ammonium iodide; silver(l) oxide; In dichloromethane; at 20 ℃; for 16h; Inert atmosphere; Molecular sieve; Darkness;
DOI:10.1021/acs.joc.5b00992

Reference yield:

: 108999-04-8
methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,3-dibromo-2,3,5-trideoxy-β-D-erythro-L-manno-non-2-ulopyranosonate

: 1262101-67-6
methyl (4'-methoxybenzyl-5-acetamido-4,7,8,9-tetra-O-acetyl-5-deoxy-3-O-acetonitrile-D-erythro-α-L-gluco-non-2-ulopyranoside)onate

Guidance literature:: Multi-step reaction with 4 steps

1: silver carbonate; silver perchlorate / dichloromethane / 0.75 h / 0 - 20 °C / Darkness

2: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 0.25 h / 20 °C / Inert atmosphere

3: camphor-sulfonic acid / 1,1-dichloroethane / 1.25 h / 0 - 20 °C / Inert atmosphere

4: silver(l) oxide / tetra-(n-butyl)ammonium iodide / dichloromethane / 16 h / 20 °C / Inert atmosphere; Molecular sieve; Darkness

With silver perchlorate; 1,8-diazabicyclo[5.4.0]undec-7-ene; silver carbonate; silver(l) oxide; tetra-(n-butyl)ammonium iodide; In 1,1-dichloroethane; dichloromethane; acetonitrile;

Reference yield:

: 109681-20-1
methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,3-anhydro-5-deoxy-β-D-erythro-L-gluco-non-2-ulopyranosonate

: 1262101-67-6
methyl (4'-methoxybenzyl-5-acetamido-4,7,8,9-tetra-O-acetyl-5-deoxy-3-O-acetonitrile-D-erythro-α-L-gluco-non-2-ulopyranoside)onate

Guidance literature:: Multi-step reaction with 2 steps

1: camphor-sulfonic acid / 1,1-dichloroethane / 1.25 h / 0 - 20 °C / Inert atmosphere

2: silver(l) oxide / tetra-(n-butyl)ammonium iodide / dichloromethane / 16 h / 20 °C / Inert atmosphere; Molecular sieve; Darkness

With silver(l) oxide; tetra-(n-butyl)ammonium iodide; In 1,1-dichloroethane; dichloromethane;