2-azidoethyl [methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosyl)oate]-(2-> 3)-(2,6-di-O-benzyl-β-D-galactopyranosyl-(1-> 4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

Base Information

• Chemical Name: 2-azidoethyl [methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosyl)oate]-(2-> 3)-(2,6-di-O-benzyl-β-D-galactopyranosyl-(1-> 4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
• CAS No.: 702686-19-9
• Molecular Formula: C₆₉H₈₂N₄O₂₃
• Molecular Weight: 1335.42

Synonyms:

Chemical Property of 2-azidoethyl [methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosyl)oate]-(2-> 3)-(2,6-di-O-benzyl-β-D-galactopyranosyl-(1-> 4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-azidoethyl [methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosyl)oate]-(2-> 3)-(2,6-di-O-benzyl-β-D-galactopyranosyl-(1-> 4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

There total 7 articles about 2-azidoethyl [methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosyl)oate]-(2-> 3)-(2,6-di-O-benzyl-β-D-galactopyranosyl-(1-> 4)-2,3,6-tri-O-benzyl-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:

(4S,5R,6R)-4-Acetoxy-5-acetylamino-2-ethylsulfanyl-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester + 2-azidoethyl (2,6-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside (316820-50-5) → 2-azidoethyl [methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosyl)oate]-(2-> 3)-(2,6-di-O-benzyl-β-D-galactopyranosyl-(1-> 4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside (702686-19-9)

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid; In acetonitrile; at -40 - -30 ℃; for 2h;

DOI:10.1023/B:RUBI.0000015775.24385.a0

Reference yield:

2,3,6,2',3',4',6'-hepta-O-acetyl-lactosyl bromide (4753-07-5) → 2-azidoethyl [methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosyl)oate]-(2-> 3)-(2,6-di-O-benzyl-β-D-galactopyranosyl-(1-> 4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside (702686-19-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 74 percent / mercury(II) cyanide; mercury(II) bromide / 4 h

2: 97 percent / NaN₃; 18-crown-6 / dimethylformamide / 18 h / 65 °C

3: sodium methylate / methanol / 24 h

4: 2.73 g / p-toluenesulfonic acid / 0.08 h / 60 °C

5: sodium hydride / dimethylformamide / 4 h

6: 900 mg / acetic acid / methanol; dimethylformamide / 5 h / 80 °C

7: 313 mg / N-iodosuccinimide; trifluoromethanesulfonic acid / acetonitrile / 2 h / -40 - -30 °C

With N-iodo-succinimide; sodium azide; 18-crown-6 ether; trifluorormethanesulfonic acid; sodium methylate; mercury(II) cyanide; sodium hydride; toluene-4-sulfonic acid; acetic acid; mercury dibromide; In methanol; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1023/B:RUBI.0000015775.24385.a0

Reference yield:

2-chloroethyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside (120232-83-9) → 2-azidoethyl [methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosyl)oate]-(2-> 3)-(2,6-di-O-benzyl-β-D-galactopyranosyl-(1-> 4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside (702686-19-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 97 percent / NaN₃; 18-crown-6 / dimethylformamide / 18 h / 65 °C

2: sodium methylate / methanol / 24 h

3: 2.73 g / p-toluenesulfonic acid / 0.08 h / 60 °C

4: sodium hydride / dimethylformamide / 4 h

5: 900 mg / acetic acid / methanol; dimethylformamide / 5 h / 80 °C

6: 313 mg / N-iodosuccinimide; trifluoromethanesulfonic acid / acetonitrile / 2 h / -40 - -30 °C

With N-iodo-succinimide; sodium azide; 18-crown-6 ether; trifluorormethanesulfonic acid; sodium methylate; sodium hydride; toluene-4-sulfonic acid; acetic acid; In methanol; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1023/B:RUBI.0000015775.24385.a0

upstream raw materials:

2-azidoethyl (2,6-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

2,3,6,2',3',4',6'-hepta-O-acetyl-lactosyl bromide

2-chloroethyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside

2-azidoethyl β-D-galactopyranosyl-(1->4)-β-D-glucopyranoside

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