methyl 2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl-(1->4)-2-acetamido-6-O-benzyl-3-O-((R)-1'-carboxyethyl)-2-deoxy-β-D-glucopyranoside

Base Information

Chemical Name:methyl 2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl-(1->4)-2-acetamido-6-O-benzyl-3-O-((R)-1'-carboxyethyl)-2-deoxy-β-D-glucopyranoside
CAS No.:666728-59-2
Molecular Formula:C₄₁H₅₀N₂O₁₃
Molecular Weight:778.854
Hs Code.:

methyl 2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl-(1->4)-2-acetamido-6-O-benzyl-3-O-((R)-1'-carboxyethyl)-2-deoxy-β-D-glucopyranoside

Synonyms:methyl 2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl-(1->4)-2-acetamido-6-O-benzyl-3-O-((R)-1'-carboxyethyl)-2-deoxy-β-D-glucopyranoside

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Chemical Property of methyl 2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl-(1->4)-2-acetamido-6-O-benzyl-3-O-((R)-1'-carboxyethyl)-2-deoxy-β-D-glucopyranoside

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Technology Process of methyl 2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl-(1->4)-2-acetamido-6-O-benzyl-3-O-((R)-1'-carboxyethyl)-2-deoxy-β-D-glucopyranoside

There total 14 articles about methyl 2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl-(1->4)-2-acetamido-6-O-benzyl-3-O-((R)-1'-carboxyethyl)-2-deoxy-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: 59.0%

: 29617-66-1
(S)-2-chloropropanoic acid

: N-[(2R,4aR,6S,7R,8R,8aS)-6-((2R,3S,4R,5R,6R)-5-Acetylamino-2-benzyloxymethyl-4-hydroxy-6-methoxy-tetrahydro-pyran-3-yloxy)-8-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide

: 666728-59-2
methyl 2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl-(1->4)-2-acetamido-6-O-benzyl-3-O-((R)-1'-carboxyethyl)-2-deoxy-β-D-glucopyranoside

Guidance literature:: With 4 Angstroem molecular seives; sodium hydride; In N,N-dimethyl-formamide; at 20 ℃;
DOI:10.1021/jo035397e

Reference yield:

: 81927-55-1
O-benzyl 2,2,2-trichloroacetimidate

: 666728-59-2
methyl 2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl-(1->4)-2-acetamido-6-O-benzyl-3-O-((R)-1'-carboxyethyl)-2-deoxy-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 8 steps

1: 67 percent / 4 Angstroem molecular sieves; CF₃SO₃H / CH₂Cl₂; hexane / 1 h / cooling

2: 72 percent / Bu₄NF / tetrahydrofuran / 4 h / -20 °C

3: DBU / CH₂Cl₂ / 2 h

4: 4 Angstroem molecular sieves; trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / -5 °C

5: NaOH / dioxane; H₂O / 4 h / 20 °C

6: pyridine / 20 °C

7: NaOMe / methanol / 0.5 h / 20 °C

8: 59 percent / 4 Angstroem molecular seives; NaH / dimethylformamide / 20 °C

With pyridine; sodium hydroxide; trifluorormethanesulfonic acid; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; 4 Angstroem molecular seives; tetrabutyl ammonium fluoride; sodium methylate; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/jo035397e

Reference yield:

: 87038-18-4
methyl 2-acetylamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside

: 666728-59-2
methyl 2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl-(1->4)-2-acetamido-6-O-benzyl-3-O-((R)-1'-carboxyethyl)-2-deoxy-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1: pyridine / CH₂Cl₂ / 20 °C

2: 4 Angstroem molecular sieves; trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / -5 °C

3: NaOH / dioxane; H₂O / 4 h / 20 °C

4: pyridine / 20 °C

5: NaOMe / methanol / 0.5 h / 20 °C

6: 59 percent / 4 Angstroem molecular seives; NaH / dimethylformamide / 20 °C

With pyridine; sodium hydroxide; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; 4 Angstroem molecular seives; sodium methylate; sodium hydride; In 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/jo035397e