3-azidopropyl 2,6-di-O-benzyl-3,4-di-O-isopropylidene-α-D-galactopyranosyl-(1->4)-6-O-benzoyl-2,3-di-O-benzyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

Base Information

• Chemical Name: 3-azidopropyl 2,6-di-O-benzyl-3,4-di-O-isopropylidene-α-D-galactopyranosyl-(1->4)-6-O-benzoyl-2,3-di-O-benzyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
• CAS No.: 229954-84-1
• Molecular Formula: C₈₀H₈₇N₃O₁₇
• Molecular Weight: 1362.58
• Mol file: 229954-84-1.mol

Synonyms:3-azidopropyl 2,6-di-O-benzyl-3,4-di-O-isopropylidene-α-D-galactopyranosyl-(1->4)-6-O-benzoyl-2,3-di-O-benzyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

Chemical Property of 3-azidopropyl 2,6-di-O-benzyl-3,4-di-O-isopropylidene-α-D-galactopyranosyl-(1->4)-6-O-benzoyl-2,3-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 3-azidopropyl 2,6-di-O-benzyl-3,4-di-O-isopropylidene-α-D-galactopyranosyl-(1->4)-6-O-benzoyl-2,3-di-O-benzyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

There total 6 articles about 3-azidopropyl 2,6-di-O-benzyl-3,4-di-O-isopropylidene-α-D-galactopyranosyl-(1->4)-6-O-benzoyl-2,3-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: 47.0%

ethyl 2,6-di-O-benzyl-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside (213459-71-3) + 3-azidopropyl 6-O-benzoyl-2,3-di-O-benzyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside (229954-83-0) → 3-azidopropyl 2,6-di-O-benzyl-3,4-di-O-isopropylidene-α-D-galactopyranosyl-(1->4)-6-O-benzoyl-2,3-di-O-benzyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside (229954-84-1)

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; In dichloromethane; at -40 ℃; for 1.5h;

DOI:10.1016/S0008-6215(99)00018-X

Reference yield:

benzoyl chloride (98-88-4) → 3-azidopropyl 2,6-di-O-benzyl-3,4-di-O-isopropylidene-α-D-galactopyranosyl-(1->4)-6-O-benzoyl-2,3-di-O-benzyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside (229954-84-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 76 percent / 2,6-lutidine / CH₂Cl₂ / 6 h / 0 °C

2: 47 percent / powdered 4 Angstroem molecular sieves; NIS; TfOH / CH₂Cl₂ / 1.5 h / -40 °C

With 2,6-dimethylpyridine; N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; In dichloromethane; 1: Acylation / 2: Alkylation;

DOI:10.1016/S0008-6215(99)00018-X

Reference yield:

3-azidopropyl (β-O-D-galactopyranosyl)-(1→4)-O-β-D-glucopyranoside (229954-81-8) → 3-azidopropyl 2,6-di-O-benzyl-3,4-di-O-isopropylidene-α-D-galactopyranosyl-(1->4)-6-O-benzoyl-2,3-di-O-benzyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside (229954-84-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 2.2 g / p-toluenesulfonic acid / acetonitrile / 6 h / 20 °C

2: 87 percent / NaH / dimethylformamide / 3 h / 20 °C

3: aq. HOAc / 1 h / 60 °C

4: 76 percent / 2,6-lutidine / CH₂Cl₂ / 6 h / 0 °C

5: 47 percent / powdered 4 Angstroem molecular sieves; NIS; TfOH / CH₂Cl₂ / 1.5 h / -40 °C

With 2,6-dimethylpyridine; N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; sodium hydride; toluene-4-sulfonic acid; acetic acid; In dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1: Condensation / 2: Alkylation / 3: Hydrolysis / 4: Acylation / 5: Alkylation;

DOI:10.1016/S0008-6215(99)00018-X

upstream raw materials:

ethyl 2,6-di-O-benzyl-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside

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

benzoyl chloride

3-azidopropyl (β-O-D-galactopyranosyl)-(1→4)-O-β-D-glucopyranoside

Downstream raw materials:

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