methyl {2-benzyl-5-glycolylamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-5-O_glycolyl-[methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosyl)onate]-α-D-glycero-D-galacto-2-nonulopyranosid}onate

Base Information

• Chemical Name: methyl {2-benzyl-5-glycolylamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-5-O_glycolyl-[methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosyl)onate]-α-D-glycero-D-galacto-2-nonulopyranosid}onate
• CAS No.: 402948-39-4
• Molecular Formula: C₄₇H₆₂N₂O₂₆
• Molecular Weight: 1071.01

Synonyms:methyl {2-benzyl-5-glycolylamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-5-O_glycolyl-[methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosyl)onate]-α-D-glycero-D-galacto-2-nonulopyranosid}onate

Chemical Property of methyl {2-benzyl-5-glycolylamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-5-O_glycolyl-[methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosyl)onate]-α-D-glycero-D-galacto-2-nonulopyranosid}onate

Chemical Property:

Purity/Quality:

Safty Information:

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Useful:

Technology Process of methyl {2-benzyl-5-glycolylamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-5-O_glycolyl-[methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosyl)onate]-α-D-glycero-D-galacto-2-nonulopyranosid}onate

There total 8 articles about methyl {2-benzyl-5-glycolylamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-5-O_glycolyl-[methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosyl)onate]-α-D-glycero-D-galacto-2-nonulopyranosid}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%

methyl [benzyl 5-amino-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosid]onate (175877-06-2) + methyl [2-(2'-oxido-2'-oxoethyl)-5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosid]onate (119054-26-1) → methyl {2-benzyl-5-glycolylamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-5-Oglycolyl-[methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosyl)onate]-α-D-glycero-D-galacto-2-nonulopyranosid}onate (402948-39-4)

Guidance literature:

With sodium hydrogencarbonate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In acetonitrile; at 20 ℃; for 18h;

DOI:10.1021/jo015930v

Reference yield:

(4S,5R,6R)-4-Acetoxy-5-acetylamino-2-phenylsulfanyl-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester (155155-64-9) → methyl {2-benzyl-5-glycolylamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-5-Oglycolyl-[methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosyl)onate]-α-D-glycero-D-galacto-2-nonulopyranosid}onate (402948-39-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 62 percent / NIS; TfOH / acetonitrile / 1 h / -25 °C

2: 100 percent / H₂ / 10percent Pd/C / ethyl acetate / 20 h / 760.05 Torr

3: 81 percent / EDC; HOBt; NaHCO₃ / acetonitrile / 18 h / 20 °C

With N-iodo-succinimide; trifluorormethanesulfonic acid; hydrogen; sodium hydrogencarbonate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; 10percent Pd/C; In ethyl acetate; acetonitrile;

DOI:10.1021/jo015930v

Reference yield:

methyl [2-(2'-benzyloxy-2'-oxoethyl)-5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosid]onate (402948-40-7) → methyl {2-benzyl-5-glycolylamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-5-Oglycolyl-[methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosyl)onate]-α-D-glycero-D-galacto-2-nonulopyranosid}onate (402948-39-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / H₂ / 10percent Pd/C / ethyl acetate / 20 h / 760.05 Torr

2: 81 percent / EDC; HOBt; NaHCO₃ / acetonitrile / 18 h / 20 °C

With hydrogen; sodium hydrogencarbonate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; 10percent Pd/C; In ethyl acetate; acetonitrile;

DOI:10.1021/jo015930v

upstream raw materials:

methyl [benzyl 5-amino-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosid]onate

methyl [2-(2'-oxido-2'-oxoethyl)-5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosid]onate

methyl (phenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycerol-β-D-galactonon-2-ulopyranoside)onate

(4S,5R,6R)-4-Acetoxy-5-acetylamino-2-phenylsulfanyl-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester

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