methyl 2-acetamido-2-N,3-O-carbonyl-2-deoxy-6-O-[dimethyl(1,1,2-trimethylpropyl)silyl]-4-O-[2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl]-β-D-glucopyranoside

Base Information

Chemical Name:methyl 2-acetamido-2-N,3-O-carbonyl-2-deoxy-6-O-[dimethyl(1,1,2-trimethylpropyl)silyl]-4-O-[2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl]-β-D-glucopyranoside
CAS No.:847701-09-1
Molecular Formula:C₅₂H₆₇NO₁₂Si
Molecular Weight:926.189
Hs Code.:

methyl 2-acetamido-2-N,3-O-carbonyl-2-deoxy-6-O-[dimethyl(1,1,2-trimethylpropyl)silyl]-4-O-[2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl]-β-D-glucopyranoside

Synonyms:methyl 2-acetamido-2-N,3-O-carbonyl-2-deoxy-6-O-[dimethyl(1,1,2-trimethylpropyl)silyl]-4-O-[2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl]-β-D-glucopyranoside

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Chemical Property of methyl 2-acetamido-2-N,3-O-carbonyl-2-deoxy-6-O-[dimethyl(1,1,2-trimethylpropyl)silyl]-4-O-[2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl]-β-D-glucopyranoside

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Technology Process of methyl 2-acetamido-2-N,3-O-carbonyl-2-deoxy-6-O-[dimethyl(1,1,2-trimethylpropyl)silyl]-4-O-[2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl]-β-D-glucopyranoside

There total 5 articles about methyl 2-acetamido-2-N,3-O-carbonyl-2-deoxy-6-O-[dimethyl(1,1,2-trimethylpropyl)silyl]-4-O-[2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl]-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: 78.0%

: 847700-99-6
methyl 2-acetamido-2-N,3-O-carbonyl-2-deoxy-6-O-[dimethyl(1,1,2-trimethylpropyl)silyl]-β-D-glucopyranoside

: 38184-10-0
phenyl 2,3,4,5-tetra-O-benzyl-1-thio-β-D-glucopyranoside

: 847701-09-1
methyl 2-acetamido-2-N,3-O-carbonyl-2-deoxy-6-O-[dimethyl(1,1,2-trimethylpropyl)silyl]-4-O-[2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl]-β-D-glucopyranoside

Guidance literature:: With 1-benzenesulfinyl piperidine; 3 A molecular sieve; 2,4,6-tri-tert-butylpyrimidine; trifluoromethanesulfonic acid anhydride; In dichloromethane; at -60 - 20 ℃;
DOI:10.1021/jo0482559

Reference yield:

: 847700-97-4
methyl 2-acetamido-2-N,3-O-carbonyl-2-deoxy-β-D-glucopyranoside

: 847701-09-1
methyl 2-acetamido-2-N,3-O-carbonyl-2-deoxy-6-O-[dimethyl(1,1,2-trimethylpropyl)silyl]-4-O-[2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl]-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1: 92 percent / imidazole / dimethylformamide / 5 h / 20 °C

2: 78 percent / 1-benzenesulfinyl piperidine; 2,4,6-tri-tert-butylpyrimidine; molecular sieves 3 Angstroem / trifluoromethanesulfonic anhydride / CH₂Cl₂ / -60 - 20 °C

With 1H-imidazole; 1-benzenesulfinyl piperidine; 3 A molecular sieve; 2,4,6-tri-tert-butylpyrimidine; trifluoromethanesulfonic acid anhydride; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo0482559

Reference yield:

: 847700-93-0
methyl 2-amino-4,6-O-benzylidene-2-N,3-O-carbonyl-2-deoxy-β-D-glucopyranoside

: 847701-09-1
methyl 2-acetamido-2-N,3-O-carbonyl-2-deoxy-6-O-[dimethyl(1,1,2-trimethylpropyl)silyl]-4-O-[2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl]-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 89 percent / diisopropylethylamine / CH₂Cl₂ / 0 - 20 °C

2: 82 percent / H₂ / Pd/C / tetrahydrofuran / 30 h / 5171.48 Torr

3: 92 percent / imidazole / dimethylformamide / 5 h / 20 °C

4: 78 percent / 1-benzenesulfinyl piperidine; 2,4,6-tri-tert-butylpyrimidine; molecular sieves 3 Angstroem / trifluoromethanesulfonic anhydride / CH₂Cl₂ / -60 - 20 °C

With 1H-imidazole; 1-benzenesulfinyl piperidine; 3 A molecular sieve; hydrogen; N-ethyl-N,N-diisopropylamine; 2,4,6-tri-tert-butylpyrimidine; palladium on activated charcoal; trifluoromethanesulfonic acid anhydride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo0482559