N-(5-{(2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-[2-(1H-indol-3-yl)-ethoxy]-tetrahydro-pyran-2-ylmethoxy}-pentyl)-acetamide

Base Information

• Chemical Name: N-(5-{(2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-[2-(1H-indol-3-yl)-ethoxy]-tetrahydro-pyran-2-ylmethoxy}-pentyl)-acetamide
• CAS No.: 144191-86-6
• Molecular Formula: C₄₄H₅₂N₂O₇
• Molecular Weight: 720.906
• Mol file: 144191-86-6.mol

Synonyms:N-(5-{(2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-[2-(1H-indol-3-yl)-ethoxy]-tetrahydro-pyran-2-ylmethoxy}-pentyl)-acetamide

Chemical Property of N-(5-{(2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-[2-(1H-indol-3-yl)-ethoxy]-tetrahydro-pyran-2-ylmethoxy}-pentyl)-acetamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(5-{(2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-[2-(1H-indol-3-yl)-ethoxy]-tetrahydro-pyran-2-ylmethoxy}-pentyl)-acetamide

There total 12 articles about N-(5-{(2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-[2-(1H-indol-3-yl)-ethoxy]-tetrahydro-pyran-2-ylmethoxy}-pentyl)-acetamide 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:

N-(4-{(2R,3R,4S,5R,6R)-6-[2-(1-Benzenesulfonyl-1H-indol-3-yl)-ethoxy]-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-ylmethoxy}-butyl)-acetamide → N-(5-{(2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-[2-(1H-indol-3-yl)-ethoxy]-tetrahydro-pyran-2-ylmethoxy}-pentyl)-acetamide (144191-86-6)

Guidance literature:

With sodium hydroxide; In ethanol; Yield given;

DOI:10.1021/ja00049a081

Reference yield:

2-(3-indole)-ethanol (526-55-6,930395-07-6) → N-(5-{(2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-[2-(1H-indol-3-yl)-ethoxy]-tetrahydro-pyran-2-ylmethoxy}-pentyl)-acetamide (144191-86-6)

Guidance literature:

Multi-step reaction with 10 steps

1: 99 percent / imidazole / dimethylformamide / 16 h / Ambient temperature

2: 1.) NaH / 1.) DMF, RT, 30 min, 2.) DMF, RT, 16 h

3: 84 percent / tetrabutylammonium fluoride / tetrahydrofuran / 16 h / Ambient temperature

4: 64 percent / Ag₂O, 4A molecular sieves / benzene; hexane / 96 h / Ambient temperature

5: 88 percent / NaOMe / methanol / 0.33 h / Ambient temperature

6: 85 percent / imidazole / dimethylformamide / 24 h / 50 °C

7: 1.) NaH, 2.) tetrabutylammonium iodide / 1.) THF, RT, 1 h, 2.) THF, RT, 3 d

8: 94 percent / tetrabutylammonium fluoride / tetrahydrofuran / 7 h / Ambient temperature

9: 2,6-di-tert-butyl-4-methylpyridine / CH₂Cl₂ / 0.17 h

10: 1.) NaH, 3.) 5 M aq. NaOH

With 1H-imidazole; sodium hydroxide; 2,6-di-tert-butyl-4-methylpyridine; 4 A molecular sieve; tetrabutyl ammonium fluoride; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; silver(l) oxide; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; benzene;

Reference yield:

3-(2-((tert-butyldimethylsilyl)oxy)ethyl)-1H-indole (101079-48-5) → N-(5-{(2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-[2-(1H-indol-3-yl)-ethoxy]-tetrahydro-pyran-2-ylmethoxy}-pentyl)-acetamide (144191-86-6)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) NaH / 1.) DMF, RT, 30 min, 2.) DMF, RT, 16 h

2: 84 percent / tetrabutylammonium fluoride / tetrahydrofuran / 16 h / Ambient temperature

3: 64 percent / Ag₂O, 4A molecular sieves / benzene; hexane / 96 h / Ambient temperature

4: 88 percent / NaOMe / methanol / 0.33 h / Ambient temperature

5: 85 percent / imidazole / dimethylformamide / 24 h / 50 °C

6: 1.) NaH, 2.) tetrabutylammonium iodide / 1.) THF, RT, 1 h, 2.) THF, RT, 3 d

7: 94 percent / tetrabutylammonium fluoride / tetrahydrofuran / 7 h / Ambient temperature

8: 2,6-di-tert-butyl-4-methylpyridine / CH₂Cl₂ / 0.17 h

9: 1.) NaH, 3.) 5 M aq. NaOH

With 1H-imidazole; sodium hydroxide; 2,6-di-tert-butyl-4-methylpyridine; 4 A molecular sieve; tetrabutyl ammonium fluoride; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; silver(l) oxide; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; benzene;

upstream raw materials:

N‐(5‐hydroxypentyl)acetamide

2-(1phenylsulfonyl-indol-3yl)ethyl-2,3,4-tri-O-benzyl-6-O-trifluoromethylsulfonyl-β-D-glucopyranoside

2-(3-indole)-ethanol

3-(2-((tert-butyldimethylsilyl)oxy)ethyl)-1H-indole