5-amino-2,3,6-tri-O-benzyl-5-deoxy-4-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-1-thio-D-gluconolactam

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)-1-thio-D-gluconolactam
• CAS No.: 244036-97-3
• Molecular Formula: C₆₁H₆₃NO₉S
• Molecular Weight: 986.239
• Mol file: 244036-97-3.mol

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

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)-1-thio-D-gluconolactam

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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)-1-thio-D-gluconolactam

There total 4 articles about 5-amino-2,3,6-tri-O-benzyl-5-deoxy-4-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-1-thio-D-gluconolactam 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: 87.0%

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 (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)-1-thio-D-gluconolactam (244036-97-3)

Guidance literature:

With Lawessons reagent; In toluene; at 40 ℃; for 2h;

DOI:10.1002/(SICI)1522-2675(19990707)82:7<963::AID-HLCA963>3.0.CO;2-V

Reference yield:

2,3,6-tris-O-(phenylmethyl)-4-O-[2,3,4,6-tetrakis-O-(phenylmethyl)-β-D-glucopyranosyl]-D-glucopyranoside (148968-90-5) → 5-amino-2,3,6-tri-O-benzyl-5-deoxy-4-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-1-thio-D-gluconolactam (244036-97-3)

Guidance literature:

Multi-step reaction with 4 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

4.1: 87 percent / Lawesson's reagent / toluene / 2 h / 40 °C

With Lawessons reagent; ammonia; Dess-Martin periodane; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In dichloromethane; dimethyl sulfoxide; toluene; 1.1: Oxidation / 2.1: amidation / 3.1: Oxidation / 3.2: Reduction / 4.1: thionation;

DOI:10.1002/(SICI)1522-2675(19990707)82:7<963::AID-HLCA963>3.0.CO;2-V

Reference yield:

2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-D-glucono-1,5-lactone (88970-25-6) → 5-amino-2,3,6-tri-O-benzyl-5-deoxy-4-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-1-thio-D-gluconolactam (244036-97-3)

Guidance literature:

Multi-step reaction with 3 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

3.1: 87 percent / Lawesson's reagent / toluene / 2 h / 40 °C

With Lawessons reagent; ammonia; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In dichloromethane; dimethyl sulfoxide; toluene; 1.1: amidation / 2.1: Oxidation / 2.2: Reduction / 3.1: thionation;

DOI:10.1002/(SICI)1522-2675(19990707)82:7<963::AID-HLCA963>3.0.CO;2-V

upstream raw materials:

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

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

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

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

Downstream raw materials:

(5R,6R,7S,8S)-7,8-bis(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydro-6-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyloxy)imidazo[1,2-a]pyridine

(5R,6R,7S,8S)-7,8-bis(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydro-2,3-diiodo-6-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyloxy)imidazo[1,2-a]pyridine

(5R,6R,7S,8R)-7,8-bis(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydro-2,3-diiodo-6-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyloxy)imidazo[1,2-a]pyridine

(5R,6R,7S,8R)-7,8-bis(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydro-2-iodo-6-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyloxy)imidazo[1,2-a]pyridine