2-(N-(phenylsulfonyl)indol-3-yl)ethyl 2,3-di-O-benzyl-4-deoxy-6-O-(5-phthalimidopentyl)-β-D-glucopyranoside

Base Information

• Chemical Name: 2-(N-(phenylsulfonyl)indol-3-yl)ethyl 2,3-di-O-benzyl-4-deoxy-6-O-(5-phthalimidopentyl)-β-D-glucopyranoside
• CAS No.: 149831-92-5
• Molecular Formula: C₄₉H₅₀N₂O₉S
• Molecular Weight: 843.01
• Mol file: 149831-92-5.mol

Synonyms:2-(N-(phenylsulfonyl)indol-3-yl)ethyl 2,3-di-O-benzyl-4-deoxy-6-O-(5-phthalimidopentyl)-β-D-glucopyranoside

Chemical Property of 2-(N-(phenylsulfonyl)indol-3-yl)ethyl 2,3-di-O-benzyl-4-deoxy-6-O-(5-phthalimidopentyl)-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(N-(phenylsulfonyl)indol-3-yl)ethyl 2,3-di-O-benzyl-4-deoxy-6-O-(5-phthalimidopentyl)-β-D-glucopyranoside

There total 18 articles about 2-(N-(phenylsulfonyl)indol-3-yl)ethyl 2,3-di-O-benzyl-4-deoxy-6-O-(5-phthalimidopentyl)-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: 78.0%

2,6-di-tert-butyl-4-methylpyridine (38222-83-2) + 5-phthalimido-1-pentanol (63273-48-3) + 5-phthalimidopentyl triflate (149831-83-4) + 2-(N-Phenylsulfonylindol-3-yl)-ethyl 2,3-Di-O-benzyl-4-deoxy-β-D-glucopyranoside (149831-91-4) → 2-(N-(phenylsulfonyl)indol-3-yl)ethyl 2,3-di-O-benzyl-4-deoxy-6-O-(5-phthalimidopentyl)-β-D-glucopyranoside (149831-92-5)

Guidance literature:

With trifluoromethylsulfonic anhydride; In dichloromethane;

Reference yield:

methyl 2,3,6-tri-O-benzoyl-α-D-glucopyranoside (57784-06-2,6344-46-3) → 2-(N-(phenylsulfonyl)indol-3-yl)ethyl 2,3-di-O-benzyl-4-deoxy-6-O-(5-phthalimidopentyl)-β-D-glucopyranoside (149831-92-5)

Guidance literature:

Multi-step reaction with 10 steps

1: 1.) sodium bis(trimethylsilyl)amide / 1.) THF, -78 deg C, 20 min, 2.) THF, from -78 deg C to RT, 50 min

2: tributyltin hydride, AIBN / toluene / 4 h / Heating

3: 85 percent / BF₃*OEt₂ / 4 h / Ambient temperature

4: 100 percent / 30percent aq. HBr, acetic acid / CH₂Cl₂ / 4 h / Ambient temperature

5: 81 percent / Ag₂O, 4A molecular sieves / hexane; benzene / 2 h / Ambient temperature

6: 91 percent / CH₃ONa / methanol / 16 h

7: 97 percent / imidazole / dimethylformamide / 48 h / 70 °C

8: 1.) NaH / 1.) THF, RT, 30 min, 2.) THF, RT, 3 d

9: 85 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / Ambient temperature

10: NaH, 2,6-di-tert-butyl-4-methylpyridine / CH₂Cl₂ / 48 h / Ambient temperature

With 1H-imidazole; 2,6-di-tert-butyl-4-methylpyridine; 2,2'-azobis(isobutyronitrile); 4 A molecular sieve; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen bromide; tri-n-butyl-tin hydride; sodium methylate; sodium hexamethyldisilazane; sodium hydride; acetic acid; silver(l) oxide; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; benzene;

Reference yield:

Methyl-2,3,6-tri-O-benzoyl-4-desoxy-α-D-xylo-hexopyranosid (19488-41-6) → 2-(N-(phenylsulfonyl)indol-3-yl)ethyl 2,3-di-O-benzyl-4-deoxy-6-O-(5-phthalimidopentyl)-β-D-glucopyranoside (149831-92-5)

Guidance literature:

Multi-step reaction with 8 steps

1: 85 percent / BF₃*OEt₂ / 4 h / Ambient temperature

2: 100 percent / 30percent aq. HBr, acetic acid / CH₂Cl₂ / 4 h / Ambient temperature

3: 81 percent / Ag₂O, 4A molecular sieves / hexane; benzene / 2 h / Ambient temperature

4: 91 percent / CH₃ONa / methanol / 16 h

5: 97 percent / imidazole / dimethylformamide / 48 h / 70 °C

6: 1.) NaH / 1.) THF, RT, 30 min, 2.) THF, RT, 3 d

7: 85 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / Ambient temperature

8: NaH, 2,6-di-tert-butyl-4-methylpyridine / CH₂Cl₂ / 48 h / Ambient temperature

With 1H-imidazole; 2,6-di-tert-butyl-4-methylpyridine; 4 A molecular sieve; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen bromide; sodium methylate; sodium hydride; acetic acid; silver(l) oxide; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; benzene;

upstream raw materials:

5-phthalimidopentyl triflate

2-(N-Phenylsulfonylindol-3-yl)-ethyl 2,3-Di-O-benzyl-4-deoxy-β-D-glucopyranoside

methyl 2,3,6-tri-O-benzoyl-α-D-glucopyranoside

2-(3-indole)-ethanol