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

Base Information

Chemical Name: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
CAS No.:402948-40-7
Molecular Formula:C₂₉H₃₇NO₁₅
Molecular Weight:639.61
Hs Code.:

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 2 articles about 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 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: 62.0%

: 30379-58-9
benzyl glycolate

: 155155-64-9
(4S,5R,6R)-4-Acetoxy-5-acetylamino-2-phenylsulfanyl-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester

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

: 402948-40-7
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

Guidance literature:: With N-iodo-succinimide; trifluorormethanesulfonic acid; In acetonitrile; at -25 ℃; for 1h;
DOI:10.1021/jo015930v

Reference yield:

: 30379-58-9
benzyl glycolate

: 67670-69-3
N-acetyl-4,7,8,9-tetra-O-acetyl-2-chloro-2-deoxyneuraminic acid methyl ester

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

: 402948-40-7
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

Guidance literature:: With silver perchlorate; silver carbonate; In dichloromethane; at 20 ℃; for 24h; Darkness; Inert atmosphere;

Reference yield:

: 402948-40-7
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

: O_glycolyl-(5-acetamido-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopuranosylonic acid)-(2-5)-2-benzyl-5-glycolylamido-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosonic acid

Guidance literature:: Multi-step reaction with 4 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

3: 95 percent / LiCl; pyridine / 16 h / 120 °C

4: 94 percent / aq. NaOH / 3 h / 20 °C

With pyridine; sodium hydroxide; hydrogen; sodium hydrogencarbonate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; lithium chloride; 10percent Pd/C; In ethyl acetate; acetonitrile;
DOI:10.1021/jo015930v