methyl (2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-galactopyranosyl)(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Base Information

Chemical Name:methyl (2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-galactopyranosyl)(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
CAS No.:278784-86-4
Molecular Formula:C₄₃H₄₈N₂O₁₅
Molecular Weight:832.859
Hs Code.:

Synonyms:methyl (2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-galactopyranosyl)(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

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Chemical Property of methyl (2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-galactopyranosyl)(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

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Technology Process of methyl (2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-galactopyranosyl)(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

There total 9 articles about methyl (2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-galactopyranosyl)(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 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: 74.0%

: 108-24-7
acetic anhydride

: 278784-84-2
methyl (3,4,6-tri-O-acetyl-2-deoxy-2-(2',2',2'-trichloroethoxycarbonylamino)-β-D-galactopyranosyl)(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

: 278784-86-4
methyl (2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-galactopyranosyl)(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Guidance literature:: methyl (3,4,6-tri-O-acetyl-2-deoxy-2-(2',2',2'-trichloroethoxycarbonylamino)-β-D-galactopyranosyl)(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside; With cadmium; In acetic acid; N,N-dimethyl-formamide;

acetic anhydride; In methanol; for 1h; Further stages.;
DOI:10.1021/jo991812k

Reference yield:

: 76101-14-9
methyl-2-desoxy-2-phthalimido-β-D-glucopyranoside

: 278784-86-4
methyl (2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-galactopyranosyl)(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1.1: p-TsOH / acetonitrile / 0.33 h

2.1: NaH / dimethylformamide / 20 °C

3.1: methyl orange; NaCNBH₃; HCl / tetrahydrofuran; diethyl ether

4.1: 87 percent / 4 Angstroem MS; NIS; AgOTf / CH₂Cl₂ / 0.33 h / 20 °C

5.1: Cd / dimethylformamide; acetic acid

5.2: 74 percent / methanol / 1 h

With hydrogenchloride; N-iodo-succinimide; 4 Angstroem MS; silver trifluoromethanesulfonate; methyl orange; sodium hydride; sodium cyanoborohydride; toluene-4-sulfonic acid; cadmium; In tetrahydrofuran; diethyl ether; dichloromethane; acetic acid; N,N-dimethyl-formamide; acetonitrile; 1.1: Condensation / 2.1: Alkylation / 3.1: Reduction / 4.1: Condensation / 5.1: Reduction / 5.2: Acetylation;
DOI:10.1021/jo991812k

Reference yield:

: 70831-94-6
3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranosyl bromide

: 278784-86-4
methyl (2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-galactopyranosyl)(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1.1: lutidine; 4 Angstroem MS; AgOTf / CH₂Cl₂ / 3 h

2.1: NaOMe / methanol / 3 h

3.1: p-TsOH / acetonitrile / 0.33 h

4.1: NaH / dimethylformamide / 20 °C

5.1: methyl orange; NaCNBH₃; HCl / tetrahydrofuran; diethyl ether

6.1: 87 percent / 4 Angstroem MS; NIS; AgOTf / CH₂Cl₂ / 0.33 h / 20 °C

7.1: Cd / dimethylformamide; acetic acid

7.2: 74 percent / methanol / 1 h

With hydrogenchloride; N-iodo-succinimide; 4 Angstroem MS; lutidine; sodium methylate; silver trifluoromethanesulfonate; methyl orange; sodium hydride; sodium cyanoborohydride; toluene-4-sulfonic acid; cadmium; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetic acid; N,N-dimethyl-formamide; acetonitrile; 1.1: Substitution / 2.1: Deacetylation / 3.1: Condensation / 4.1: Alkylation / 5.1: Reduction / 6.1: Condensation / 7.1: Reduction / 7.2: Acetylation;
DOI:10.1021/jo991812k