octyl 2,3,4-tri-O-benzyl-6-O-diphenoxyphosphono-β-D-galactopyranosyl-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside

Base Information

• Chemical Name: octyl 2,3,4-tri-O-benzyl-6-O-diphenoxyphosphono-β-D-galactopyranosyl-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside
• CAS No.: 503602-49-1
• Molecular Formula: C₆₉H₈₀NO₁₄P
• Molecular Weight: 1178.37

Synonyms:octyl 2,3,4-tri-O-benzyl-6-O-diphenoxyphosphono-β-D-galactopyranosyl-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside

Chemical Property of octyl 2,3,4-tri-O-benzyl-6-O-diphenoxyphosphono-β-D-galactopyranosyl-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of octyl 2,3,4-tri-O-benzyl-6-O-diphenoxyphosphono-β-D-galactopyranosyl-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside

There total 11 articles about octyl 2,3,4-tri-O-benzyl-6-O-diphenoxyphosphono-β-D-galactopyranosyl-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-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: 72.0%

chlorophosphoric acid diphenyl ester (2524-64-3) + octyl 2,3,4-tri-O-benzyl-β-D-galactopyranosyl-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside (503602-30-0) → octyl 2,3,4-tri-O-benzyl-6-O-diphenoxyphosphono-β-D-galactopyranosyl-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside (503602-49-1)

Guidance literature:

With dmap; In pyridine; at 20 ℃; for 24h;

DOI:10.1016/S0008-6215(02)00178-7

Reference yield:

ethyl 2,3-di-O-acetyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside (20701-62-6,56119-29-0,147332-52-3) → octyl 2,3,4-tri-O-benzyl-6-O-diphenoxyphosphono-β-D-galactopyranosyl-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside (503602-49-1)

Guidance literature:

Multi-step reaction with 10 steps

1: 61 percent / N-iodosuccinimide; silver triflate; 4A molecular sieves / CH₂Cl₂

2: 70 percent / sodium / methanol / 48 h / 20 °C

3: 66 percent / NaH; tetrabutyl ammonium iodide / dimethylformamide

4: 92 percent / AcOH / 4 h / 80 °C

5: 100 percent / diisopropylethylamine / CH₂Cl₂ / 8 h / 20 °C

6: 84 percent / NaH; tetrabutylammonium iodide / dimethylformamide

7: 97 percent / trifluoroacetic acid; triisopropylsilane / CH₂Cl₂ / 2 h / 20 °C

8: ethylenediamine / 2-methyl-propan-2-ol / 30 h / 90 °C

9: 255 mg / triethylamine / methanol / 2 h / 20 °C

10: 72 percent / 4-dimethyalminopyridine / pyridine / 24 h / 20 °C

With dmap; N-iodo-succinimide; chlorotriisopropylsilane; 4 A molecular sieve; silver trifluoromethanesulfonate; sodium; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; ethylenediamine; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In pyridine; methanol; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1016/S0008-6215(02)00178-7

Reference yield:

octyl 4,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (145064-88-6) → octyl 2,3,4-tri-O-benzyl-6-O-diphenoxyphosphono-β-D-galactopyranosyl-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside (503602-49-1)

Guidance literature:

Multi-step reaction with 10 steps

1: 61 percent / N-iodosuccinimide; silver triflate; 4A molecular sieves / CH₂Cl₂

2: 70 percent / sodium / methanol / 48 h / 20 °C

3: 66 percent / NaH; tetrabutyl ammonium iodide / dimethylformamide

4: 92 percent / AcOH / 4 h / 80 °C

5: 100 percent / diisopropylethylamine / CH₂Cl₂ / 8 h / 20 °C

6: 84 percent / NaH; tetrabutylammonium iodide / dimethylformamide

7: 97 percent / trifluoroacetic acid; triisopropylsilane / CH₂Cl₂ / 2 h / 20 °C

8: ethylenediamine / 2-methyl-propan-2-ol / 30 h / 90 °C

9: 255 mg / triethylamine / methanol / 2 h / 20 °C

10: 72 percent / 4-dimethyalminopyridine / pyridine / 24 h / 20 °C

With dmap; N-iodo-succinimide; chlorotriisopropylsilane; 4 A molecular sieve; silver trifluoromethanesulfonate; sodium; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; ethylenediamine; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In pyridine; methanol; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1016/S0008-6215(02)00178-7

upstream raw materials:

chlorophosphoric acid diphenyl ester

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

ethyl 2,3-di-O-acetyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside

octyl 4,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

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