5-amino-2,3,6-tri-O-benzyl-5-deoxy-4-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-L-glucono-1,5-lactam

Base Information

Chemical Name:5-amino-2,3,6-tri-O-benzyl-5-deoxy-4-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-L-glucono-1,5-lactam
CAS No.:221681-65-8
Molecular Formula:C₆₁H₆₃NO₁₀
Molecular Weight:970.172
Hs Code.:

Synonyms:5-amino-2,3,6-tri-O-benzyl-5-deoxy-4-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-L-glucono-1,5-lactam

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Chemical Property of 5-amino-2,3,6-tri-O-benzyl-5-deoxy-4-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-L-glucono-1,5-lactam

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Technology Process of 5-amino-2,3,6-tri-O-benzyl-5-deoxy-4-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-L-glucono-1,5-lactam

There total 3 articles about 5-amino-2,3,6-tri-O-benzyl-5-deoxy-4-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-L-glucono-1,5-lactam 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:

: 244036-92-8
2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-D-gluconamide

: 221681-65-8
5-amino-2,3,6-tri-O-benzyl-5-deoxy-4-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-L-glucono-1,5-lactam

: 5-amino-2,3,6-tri-O-benzyl-5-deoxy-4-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-L-idono-1,5-lactam

Guidance literature:: 2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-D-gluconamide; With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In dimethyl sulfoxide; at 23 ℃; for 5h;

With sodium cyanoborohydride; In formic acid; acetonitrile; at 35 ℃; for 5h;
DOI:10.1002/(SICI)1522-2675(19990707)82:7<963::AID-HLCA963>3.0.CO;2-V

Reference yield:

: 148968-90-5
2,3,6-tris-O-(phenylmethyl)-4-O-[2,3,4,6-tetrakis-O-(phenylmethyl)-β-D-glucopyranosyl]-D-glucopyranoside

: 221681-65-8
5-amino-2,3,6-tri-O-benzyl-5-deoxy-4-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-L-glucono-1,5-lactam

Guidance literature:: Multi-step reaction with 3 steps

1.1: 21.7 g / Dess-Martin periodinane / CH₂Cl₂ / 5 h / 23 °C

2.1: 21.8 g / NH₃ / CH₂Cl₂ / 2 h / Heating

3.1: 1-hydroxy-1,2-benzodioxol-3(1H)-one 1-oxide / dimethylsulfoxide / 5 h / 23 °C

3.2: sodium cyanoborohydride / acetonitrile; formic acid / 5 h / 35 °C

With ammonia; Dess-Martin periodane; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In dichloromethane; dimethyl sulfoxide; 1.1: Oxidation / 2.1: amidation / 3.1: Oxidation / 3.2: Reduction;
DOI:10.1002/(SICI)1522-2675(19990707)82:7<963::AID-HLCA963>3.0.CO;2-V

Reference yield:

: 88970-25-6
2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-D-glucono-1,5-lactone

: 221681-65-8
5-amino-2,3,6-tri-O-benzyl-5-deoxy-4-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-L-glucono-1,5-lactam

Guidance literature:: Multi-step reaction with 2 steps

1.1: 21.8 g / NH₃ / CH₂Cl₂ / 2 h / Heating

2.1: 1-hydroxy-1,2-benzodioxol-3(1H)-one 1-oxide / dimethylsulfoxide / 5 h / 23 °C

2.2: sodium cyanoborohydride / acetonitrile; formic acid / 5 h / 35 °C

With ammonia; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In dichloromethane; dimethyl sulfoxide; 1.1: amidation / 2.1: Oxidation / 2.2: Reduction;
DOI:10.1002/(SICI)1522-2675(19990707)82:7<963::AID-HLCA963>3.0.CO;2-V