2,3,4,6-tetra-O-benzyl-N-(O-benzyl-N-benzyloxycarbonyl-L-β-aspartyl)-α-D-glucopyranosylamine

Base Information

Chemical Name:2,3,4,6-tetra-O-benzyl-N-(O-benzyl-N-benzyloxycarbonyl-L-β-aspartyl)-α-D-glucopyranosylamine
CAS No.:85917-85-7
Molecular Formula:C₅₃H₅₄N₂O₁₀
Molecular Weight:879.019
Hs Code.:

Synonyms:2,3,4,6-tetra-O-benzyl-N-(O-benzyl-N-benzyloxycarbonyl-L-β-aspartyl)-α-D-glucopyranosylamine

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Chemical Property of 2,3,4,6-tetra-O-benzyl-N-(O-benzyl-N-benzyloxycarbonyl-L-β-aspartyl)-α-D-glucopyranosylamine

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Technology Process of 2,3,4,6-tetra-O-benzyl-N-(O-benzyl-N-benzyloxycarbonyl-L-β-aspartyl)-α-D-glucopyranosylamine

There total 10 articles about 2,3,4,6-tetra-O-benzyl-N-(O-benzyl-N-benzyloxycarbonyl-L-β-aspartyl)-α-D-glucopyranosylamine 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: 71.0%

: 136755-16-3,150446-96-1
N-acetyl-2,3,4,6-tetra-O-benzyl-N-(benzyl-N-benzyloxycarbonyl-L-β-aspartyl)-α-D-glucopyranosylamine

: 136755-17-4
N-acetyl-2,3,4,6-tetra-O-benzyl-α-D-glucopyranosylamine

: 85917-85-7
2,3,4,6-tetra-O-benzyl-N-(O-benzyl-N-benzyloxycarbonyl-L-β-aspartyl)-α-D-glucopyranosylamine

Guidance literature:: With piperidine; In N,N-dimethyl-formamide; for 5.75h;
DOI:10.1016/0008-6215(92)84171-N

Reference yield:

: 4451-36-9
2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl chloride

: 85917-85-7
2,3,4,6-tetra-O-benzyl-N-(O-benzyl-N-benzyloxycarbonyl-L-β-aspartyl)-α-D-glucopyranosylamine

Guidance literature:: Multi-step reaction with 5 steps

1.1: 78 percent / NaN₃ / hexamethylphosphoric acid triamide / 4 h / 20 °C

2.1: 86 percent / NaOMe / methanol / 2 h / 20 °C

3.1: NaH / dimethylsulfoxide / 1 h / 20 °C

3.2: 73 percent / dimethylsulfoxide / 3 h / 20 °C

4.1: H₂; Et₃N / Lindlar's catalyst / tetrahydrofuran; methanol / 16 h / 1520 Torr

5.1: HOBt; DCC / CH₂Cl₂; dimethylformamide / 13 h / 0 - 20 °C

With sodium azide; hydrogen; sodium methylate; sodium hydride; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; Lindlar's catalyst; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; 1.1: Substitution / 2.1: Substitution / 3.1: Metallation / 3.2: Etherification / 4.1: Catalytic hydrogenation / 5.1: Acylation;
DOI:10.1515/znb-1999-0519

Reference yield:

: 20379-60-6
α-D-Glucopyranosyl azide

: 85917-85-7
2,3,4,6-tetra-O-benzyl-N-(O-benzyl-N-benzyloxycarbonyl-L-β-aspartyl)-α-D-glucopyranosylamine

Guidance literature:: Multi-step reaction with 3 steps

1.1: NaH / dimethylsulfoxide / 1 h / 20 °C

1.2: 73 percent / dimethylsulfoxide / 3 h / 20 °C

2.1: H₂; Et₃N / Lindlar's catalyst / tetrahydrofuran; methanol / 16 h / 1520 Torr

3.1: HOBt; DCC / CH₂Cl₂; dimethylformamide / 13 h / 0 - 20 °C

With hydrogen; sodium hydride; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; Lindlar's catalyst; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; 1.1: Metallation / 1.2: Etherification / 2.1: Catalytic hydrogenation / 3.1: Acylation;
DOI:10.1515/znb-1999-0519