methyl [2-(2'-benzyloxy-2'-oxoethyl)-5-acetoxyacetamido-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-acetoxyacetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosid]onate
CAS No.:552831-45-5
Molecular Formula:C₃₁H₃₉NO₁₇
Molecular Weight:697.647
Hs Code.:

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

There total 5 articles about methyl [2-(2'-benzyloxy-2'-oxoethyl)-5-acetoxyacetamido-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: 96.0%

: 13831-31-7
Acetoxyacetyl chloride

: 552831-44-4
(2R,4S,5R,6R)-4-Acetoxy-5-amino-2-benzyloxycarbonylmethoxy-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester

: 552831-45-5
methyl [2-(2'-benzyloxy-2'-oxoethyl)-5-acetoxyacetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosid]onate

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃; for 2h;
DOI:10.1002/chem.200390101

Reference yield: 80.0%

: 13831-31-7
Acetoxyacetyl chloride

: 552831-43-3
(2R,4S,5R,6R)-4-Acetoxy-2-benzyloxycarbonylmethoxy-6-((1S,2R)-1,2,3-triacetoxy-propyl)-5-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-2-carboxylic acid methyl ester

: 552831-45-5
methyl [2-(2'-benzyloxy-2'-oxoethyl)-5-acetoxyacetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosid]onate

Guidance literature:: (2R,4S,5R,6R)-4-Acetoxy-2-benzyloxycarbonylmethoxy-6-((1S,2R)-1,2,3-triacetoxy-propyl)-5-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-2-carboxylic acid methyl ester; With acetic acid; zinc; at 20 ℃; for 1.5h;

Acetoxyacetyl chloride; With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃; for 2h; Further stages.;
DOI:10.1002/chem.200390101

Reference yield:

: 30379-58-9
benzyl glycolate

: 552831-45-5
methyl [2-(2'-benzyloxy-2'-oxoethyl)-5-acetoxyacetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosid]onate

Guidance literature:: Multi-step reaction with 2 steps

1.1: 67 percent / molecular sieves 4 Angstroem; NIS; TfOH / acetonitrile / 1 h / -25 °C

2.1: Zn; glacial AcOH / 1.5 h / 20 °C

2.2: 80 percent / iPr₂NEt / CH₂Cl₂ / 2 h / 0 °C

With N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; acetic acid; zinc; In acetonitrile;
DOI:10.1002/chem.200390101