2-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-L-(N-carbobenzyloxy)tryptophan

Base Information

Chemical Name:2-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-L-(N-carbobenzyloxy)tryptophan
CAS No.:849359-37-1
Molecular Formula:C₅₃H₅₂N₂O₉
Molecular Weight:861.004
Hs Code.:

Synonyms:2-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-L-(N-carbobenzyloxy)tryptophan

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Chemical Property of 2-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-L-(N-carbobenzyloxy)tryptophan

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Technology Process of 2-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-L-(N-carbobenzyloxy)tryptophan

There total 7 articles about 2-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-L-(N-carbobenzyloxy)tryptophan 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: 85.0%

: 849359-35-9
2-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-L-(N-carbobenzyloxy)tryptophan methyl ester

: 849359-37-1
2-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-L-(N-carbobenzyloxy)tryptophan

Guidance literature:: With lithium hydroxide; In isopropyl alcohol; at 20 ℃; for 25h;
DOI:10.1039/b414905j

Reference yield:

: 3866-62-4,3964-13-4,56822-48-1,56822-49-2,78136-22-8,80300-30-7,80300-97-6,83462-68-4,83462-69-5,94943-10-9
1-O-acetyl-2,3,4,6-tetra-O-benzyl-β-D-galactopyranoside

: 849359-37-1
2-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-L-(N-carbobenzyloxy)tryptophan

Guidance literature:: Multi-step reaction with 6 steps

1: TMSOTf / CH₂Cl₂ / 16.5 h / 5 °C

2: 289 mg / aq. n-Bu₄NF / tetrahydrofuran / 2.33 h / 20 °C

3: 46 percent / Ph₃P; CuI; n-BuNH₂ / Pd₂[dba]3*CHCl₃ / tetrahydrofuran / 60 °C

4: 90 percent / n-Bu₄NF / tetrahydrofuran / 0.83 h / 20 °C

5: 43 percent / Sc(ClO₄)3; 5 Angstroem molecular sieves / CH₂Cl₂ / 2 h / 0 °C

6: 85 percent / aq. LiOH / propan-2-ol / 25 h / 20 °C

With lithium hydroxide; copper(l) iodide; scandium(III) perchlorate; trimethylsilyl trifluoromethanesulfonate; 5A molecular sieve; tetrabutyl ammonium fluoride; N-butylamine; triphenylphosphine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; In tetrahydrofuran; dichloromethane; isopropyl alcohol; 3: Sonogashira coupling;
DOI:10.1039/b414905j

Reference yield:

: 287962-77-0
(2R,3S,4R,5S,6R)-3,4,5-tribenzyloxy-2-(benzyloxymethyl)-6-ethynyl-tetrahydropyran

: 849359-37-1
2-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-L-(N-carbobenzyloxy)tryptophan

Guidance literature:: Multi-step reaction with 4 steps

1: 46 percent / Ph₃P; CuI; n-BuNH₂ / Pd₂[dba]3*CHCl₃ / tetrahydrofuran / 60 °C

2: 90 percent / n-Bu₄NF / tetrahydrofuran / 0.83 h / 20 °C

3: 43 percent / Sc(ClO₄)3; 5 Angstroem molecular sieves / CH₂Cl₂ / 2 h / 0 °C

4: 85 percent / aq. LiOH / propan-2-ol / 25 h / 20 °C

With lithium hydroxide; copper(l) iodide; scandium(III) perchlorate; 5A molecular sieve; tetrabutyl ammonium fluoride; N-butylamine; triphenylphosphine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; In tetrahydrofuran; dichloromethane; isopropyl alcohol; 1: Sonogashira coupling;
DOI:10.1039/b414905j