methyl 2-acetamido-6-O-benzyl-2-N,3-O-carbonyl-2-deoxy-[2,3-O-carbonate-4-O-benzoyl-α-L-rhamnopyranosyl]-(1->4)-α-D-glucopyranoside

Base Information

Chemical Name:methyl 2-acetamido-6-O-benzyl-2-N,3-O-carbonyl-2-deoxy-[2,3-O-carbonate-4-O-benzoyl-α-L-rhamnopyranosyl]-(1->4)-α-D-glucopyranoside
CAS No.:526199-57-5
Molecular Formula:C₃₁H₃₃NO₁₃
Molecular Weight:627.602
Hs Code.:

Synonyms:methyl 2-acetamido-6-O-benzyl-2-N,3-O-carbonyl-2-deoxy-[2,3-O-carbonate-4-O-benzoyl-α-L-rhamnopyranosyl]-(1->4)-α-D-glucopyranoside

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Chemical Property of methyl 2-acetamido-6-O-benzyl-2-N,3-O-carbonyl-2-deoxy-[2,3-O-carbonate-4-O-benzoyl-α-L-rhamnopyranosyl]-(1->4)-α-D-glucopyranoside

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Technology Process of methyl 2-acetamido-6-O-benzyl-2-N,3-O-carbonyl-2-deoxy-[2,3-O-carbonate-4-O-benzoyl-α-L-rhamnopyranosyl]-(1->4)-α-D-glucopyranoside

There total 7 articles about methyl 2-acetamido-6-O-benzyl-2-N,3-O-carbonyl-2-deoxy-[2,3-O-carbonate-4-O-benzoyl-α-L-rhamnopyranosyl]-(1->4)-α-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:

: 128657-58-9
methyl 2-amino-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside

: 526199-57-5
methyl 2-acetamido-6-O-benzyl-2-N,3-O-carbonyl-2-deoxy-[2,3-O-carbonate-4-O-benzoyl-α-L-rhamnopyranosyl]-(1->4)-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1.1: NaHCO₃ / H₂O; acetonitrile / 3 h / 0 °C

1.2: 76 percent / Amberlite IR-120NA / dimethylformamide / 20 °C

2.1: 92 percent / diisopropylethylamine / CH₂Cl₂ / 6 h

3.1: 80 percent / HCl; sodium cyanoborohydride / diethyl ether; tetrahydrofuran / 1.5 h / 0 °C

4.1: 66 percent / 1-benzenesulfinyl piperidine; 2,4,6-tri-tert-butylpyrimidine; molecular sieves 3 Angstroem / trifluoromethanesulfonic anhydride / CH₂Cl₂ / -60 - 20 °C

With hydrogenchloride; 1-benzenesulfinyl piperidine; 3 A molecular sieve; sodium cyanoborohydride; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; 2,4,6-tri-tert-butylpyrimidine; trifluoromethanesulfonic acid anhydride; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetonitrile;
DOI:10.1021/jo0482559

Reference yield:

: 99679-74-0
Methyl-4,6-O-benzyliden-2-desoxy-2-<(methoxycarbonyl)amino>-α-D-glucopyranosid

: 526199-57-5
methyl 2-acetamido-6-O-benzyl-2-N,3-O-carbonyl-2-deoxy-[2,3-O-carbonate-4-O-benzoyl-α-L-rhamnopyranosyl]-(1->4)-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1.1: 83 percent / KOH / dioxane; 2-methoxy-ethanol / 18 h / 120 °C

2.1: NaHCO₃ / H₂O; acetonitrile / 3 h / 0 °C

2.2: 76 percent / Amberlite IR-120NA / dimethylformamide / 20 °C

3.1: 92 percent / diisopropylethylamine / CH₂Cl₂ / 6 h

4.1: 80 percent / HCl; sodium cyanoborohydride / diethyl ether; tetrahydrofuran / 1.5 h / 0 °C

5.1: 66 percent / 1-benzenesulfinyl piperidine; 2,4,6-tri-tert-butylpyrimidine; molecular sieves 3 Angstroem / trifluoromethanesulfonic anhydride / CH₂Cl₂ / -60 - 20 °C

With hydrogenchloride; potassium hydroxide; 1-benzenesulfinyl piperidine; 3 A molecular sieve; sodium cyanoborohydride; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; 2,4,6-tri-tert-butylpyrimidine; trifluoromethanesulfonic acid anhydride; In tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; 2-methoxy-ethanol; water; acetonitrile;
DOI:10.1021/jo0482559

Reference yield:

: 526199-42-8
methyl 2-amino-4,6-O-benzylidene-2-N,3-O-carbonyl-2-deoxy-α-D-glucopyranoside

: 526199-57-5
methyl 2-acetamido-6-O-benzyl-2-N,3-O-carbonyl-2-deoxy-[2,3-O-carbonate-4-O-benzoyl-α-L-rhamnopyranosyl]-(1->4)-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: 92 percent / diisopropylethylamine / CH₂Cl₂ / 6 h

2: 80 percent / HCl; sodium cyanoborohydride / diethyl ether; tetrahydrofuran / 1.5 h / 0 °C

3: 66 percent / 1-benzenesulfinyl piperidine; 2,4,6-tri-tert-butylpyrimidine; molecular sieves 3 Angstroem / trifluoromethanesulfonic anhydride / CH₂Cl₂ / -60 - 20 °C

With hydrogenchloride; 1-benzenesulfinyl piperidine; 3 A molecular sieve; sodium cyanoborohydride; N-ethyl-N,N-diisopropylamine; 2,4,6-tri-tert-butylpyrimidine; trifluoromethanesulfonic acid anhydride; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1021/jo0482559