2-(N-(phenylsulfonyl)indol-3-yl)ethyl 2,3,6-tri-O-benzoyl-4-deoxy-β-D-glucopyranoside

Base Information

• Chemical Name: 2-(N-(phenylsulfonyl)indol-3-yl)ethyl 2,3,6-tri-O-benzoyl-4-deoxy-β-D-glucopyranoside
• CAS No.: 149831-87-8
• Molecular Formula: C₄₃H₃₇NO₁₀S
• Molecular Weight: 759.833
• Mol file: 149831-87-8.mol

Synonyms:2-(N-(phenylsulfonyl)indol-3-yl)ethyl 2,3,6-tri-O-benzoyl-4-deoxy-β-D-glucopyranoside

Chemical Property of 2-(N-(phenylsulfonyl)indol-3-yl)ethyl 2,3,6-tri-O-benzoyl-4-deoxy-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 2,3,6-tri-O-benzoyl-4-deoxy-β-D-glucopyranoside

There total 9 articles about 2-(N-(phenylsulfonyl)indol-3-yl)ethyl 2,3,6-tri-O-benzoyl-4-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: 81.0%

3-(2-hydroxyethyl)-1-(benzenesulfonyl)indole (99655-69-3) + C27H23BrO7 (149850-28-2) → 2-(N-(phenylsulfonyl)indol-3-yl)ethyl 2,3,6-tri-O-benzoyl-4-deoxy-β-D-glucopyranoside (149831-87-8)

Guidance literature:

With 4 A molecular sieve; silver(l) oxide; In hexane; benzene; for 2h; Ambient temperature;

Reference yield: 81.0%

→ 2-(N-(phenylsulfonyl)indol-3-yl)ethyl 2,3,6-tri-O-benzoyl-4-deoxy-β-D-glucopyranoside (149831-87-8)

Guidance literature:

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 2,3,6-tri-O-benzoyl-4-deoxy-β-D-glucopyranoside (149831-87-8)

Guidance literature:

Multi-step reaction with 5 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

With 2,2'-azobis(isobutyronitrile); 4 A molecular sieve; boron trifluoride diethyl etherate; hydrogen bromide; tri-n-butyl-tin hydride; sodium hexamethyldisilazane; acetic acid; silver(l) oxide; In hexane; dichloromethane; toluene; benzene;

upstream raw materials:

3-(2-hydroxyethyl)-1-(benzenesulfonyl)indole

C₂₇H₂₃BrO₇

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

2-(3-indole)-ethanol

Downstream raw materials:

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

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

2-(N-(phenylsulfonyl)indol-3-yl)ethyl 4-deoxy-6-(O-tert-butyldimethylsilyl)-β-D-glucopyranoside

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