2-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannopyranosyl)-1-(p-toluenesulfonyl)indole

Base Information

Chemical Name:2-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannopyranosyl)-1-(p-toluenesulfonyl)indole
CAS No.:220339-91-3
Molecular Formula:C₄₄H₄₃NO₈S
Molecular Weight:745.893
Hs Code.:

Synonyms:2-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannopyranosyl)-1-(p-toluenesulfonyl)indole

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Chemical Property of 2-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannopyranosyl)-1-(p-toluenesulfonyl)indole

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Technology Process of 2-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannopyranosyl)-1-(p-toluenesulfonyl)indole

There total 4 articles about 2-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannopyranosyl)-1-(p-toluenesulfonyl)indole 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: 88.0%

: 220339-89-9
1-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannopyranosyl)-2-o-(p-toluenesulfoamidyl)phenylethyne

: 220339-91-3
2-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannopyranosyl)-1-(p-toluenesulfonyl)indole

Guidance literature:: With copper(l) iodide; triethylamine; In N,N-dimethyl-formamide; at 80 ℃; for 0.5h;
DOI:10.1039/b414905j

Reference yield:

: 65556-30-1
1,6-di-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannopyranoside

: 220339-91-3
2-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannopyranosyl)-1-(p-toluenesulfonyl)indole

Guidance literature:: Multi-step reaction with 4 steps

1: TMSOTf / CH₂Cl₂ / 15 h / 20 °C

2: 2.32 g / aq. n-Bu₄NF / tetrahydrofuran / 1.5 h / 20 °C

3: 96 percent / Ph₃P; CuI; n-BuNH₂ / Pd₂[dba]3*CHCl₃ / tetrahydrofuran / 3 h / 20 °C

4: 88 percent / CuI; Et₃N / dimethylformamide / 0.5 h / 80 °C

With copper(l) iodide; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; N-butylamine; triethylamine; triphenylphosphine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 3: Sonogashira coupling;
DOI:10.1039/b414905j

Reference yield:

: Acetic acid (2R,3R,4R,5R,6R)-3,4,5-tris-benzyloxy-6-trimethylsilanylethynyl-tetrahydro-pyran-2-ylmethyl ester

: 220339-91-3
2-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannopyranosyl)-1-(p-toluenesulfonyl)indole

Guidance literature:: Multi-step reaction with 3 steps

1: 2.32 g / aq. n-Bu₄NF / tetrahydrofuran / 1.5 h / 20 °C

2: 96 percent / Ph₃P; CuI; n-BuNH₂ / Pd₂[dba]3*CHCl₃ / tetrahydrofuran / 3 h / 20 °C

3: 88 percent / CuI; Et₃N / dimethylformamide / 0.5 h / 80 °C

With copper(l) iodide; tetrabutyl ammonium fluoride; N-butylamine; triethylamine; triphenylphosphine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; In tetrahydrofuran; N,N-dimethyl-formamide; 2: Sonogashira coupling;
DOI:10.1039/b414905j