2-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannopyranosyl)-L-(N-carbobenzyloxy)tryptophan methyl ester

Base Information

Chemical Name:2-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannopyranosyl)-L-(N-carbobenzyloxy)tryptophan methyl ester
CAS No.:358620-69-6
Molecular Formula:C₄₉H₅₀N₂O₁₀
Molecular Weight:826.943
Hs Code.:

Synonyms:2-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannopyranosyl)-L-(N-carbobenzyloxy)tryptophan methyl ester

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of 2-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannopyranosyl)-L-(N-carbobenzyloxy)tryptophan methyl ester

Chemical Property:

Purity/Quality:: 95% ^*data from raw suppliers

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Technology Process of 2-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannopyranosyl)-L-(N-carbobenzyloxy)tryptophan methyl ester

There total 7 articles about 2-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannopyranosyl)-L-(N-carbobenzyloxy)tryptophan methyl ester 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: 83.0%

: 104597-98-0
(S)-2-methoxycarbonyl-1-benzyloxycarbonylaziridine

: 358620-68-5
2-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannopyranosyl)-1H-indole

: 358620-69-6
2-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannopyranosyl)-L-(N-carbobenzyloxy)tryptophan methyl ester

Guidance literature:: With scandium(III) perchlorate; In dichloromethane; at 0 ℃; for 5h;
DOI:10.1039/b414905j

Reference yield:

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

: 358620-69-6
2-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannopyranosyl)-L-(N-carbobenzyloxy)tryptophan methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: TMSOTf / CH₂Cl₂ / 15 h / 20 °C

2.1: 2.32 g / aq. n-Bu₄NF / tetrahydrofuran / 1.5 h / 20 °C

3.1: 96 percent / Ph₃P; CuI; n-BuNH₂ / Pd₂[dba]3*CHCl₃ / tetrahydrofuran / 3 h / 20 °C

4.1: 88 percent / CuI; Et₃N / dimethylformamide / 0.5 h / 80 °C

5.1: n-Bu₄NF / tetrahydrofuran / 0.83 h / 20 °C

5.2: 90 percent / pyridine / 0.5 h / 20 °C

6.1: Sc(OTf)3 / CH₂Cl₂ / 3 h / 0 °C

With copper(l) iodide; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; N-butylamine; triethylamine; triphenylphosphine; scandium tris(trifluoromethanesulfonate); tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 3.1: Sonogashira coupling;
DOI:10.1039/b414905j

Reference yield:

: 220339-86-6
8-O-acetyl-3,7-anhydro-4,5,6-tri-O-benzyl-1,2-dideoxy-D-glycero-D-talo-oct-1-ynitol

: 358620-69-6
2-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannopyranosyl)-L-(N-carbobenzyloxy)tryptophan methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 96 percent / Ph₃P; CuI; n-BuNH₂ / Pd₂[dba]3*CHCl₃ / tetrahydrofuran / 3 h / 20 °C

2.1: 88 percent / CuI; Et₃N / dimethylformamide / 0.5 h / 80 °C

3.1: n-Bu₄NF / tetrahydrofuran / 0.83 h / 20 °C

3.2: 90 percent / pyridine / 0.5 h / 20 °C

4.1: Sc(OTf)3 / CH₂Cl₂ / 3 h / 0 °C

With copper(l) iodide; tetrabutyl ammonium fluoride; N-butylamine; triethylamine; triphenylphosphine; scandium tris(trifluoromethanesulfonate); tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 1.1: Sonogashira coupling;
DOI:10.1039/b414905j