2-(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl)-L-(N-carbobenzyloxyl)-tryptophan methyl ester

Base Information

Chemical Name:2-(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl)-L-(N-carbobenzyloxyl)-tryptophan methyl ester
CAS No.:887644-54-4
Molecular Formula:C₅₄H₅₄N₂O₉
Molecular Weight:875.031
Hs Code.:

Synonyms:2-(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl)-L-(N-carbobenzyloxyl)-tryptophan methyl ester

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Chemical Property of 2-(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl)-L-(N-carbobenzyloxyl)-tryptophan methyl ester

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Technology Process of 2-(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl)-L-(N-carbobenzyloxyl)-tryptophan methyl ester

There total 9 articles about 2-(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl)-L-(N-carbobenzyloxyl)-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: 49.0%

: 887644-51-1
2-(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl)-1H-indole

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

: 887644-54-4
2-(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl)-L-(N-carbobenzyloxyl)-tryptophan methyl ester

Guidance literature:: With scandium(III) perchlorate; 5A molecular sieve; In dichloromethane; at 0 ℃;
DOI:10.1039/b516282c

Reference yield:

: 4132-28-9,4291-69-4,6386-24-9,6564-72-3,59531-24-7,69257-52-9,78184-89-1,78609-16-2,78609-17-3,78609-18-4,96553-53-6,104111-61-7,131347-08-5
2,3,4,6-tetra-O-benzyl-D-mannopyranose

: 887644-54-4
2-(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl)-L-(N-carbobenzyloxyl)-tryptophan methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: Ac₂O / dimethylsulfoxide / 7 h / 20 °C

2.1: n-BuLi / tetrahydrofuran; hexane / -78 - 0 °C

2.2: 5.52 g / tetrahydrofuran; hexane / 3.5 h

3.1: Et₃SiH; BF₃*Et₂O / acetonitrile; CH₂Cl₂ / -40 °C

4.1: TBAF

5.1: PPh₃; Et₃N / Pd(OAc)2 / 60 °C

5.2: 74 percent / TBAF / tetrahydrofuran / 6 h / Heating

6.1: 49 percent / Sc(ClO₄)3; 5 Angstroem molecular sieves / CH₂Cl₂ / 0 °C

With triethylsilane; n-butyllithium; scandium(III) perchlorate; 5A molecular sieve; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; acetic anhydride; triethylamine; triphenylphosphine; palladium diacetate; In tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide; acetonitrile;
DOI:10.1039/b516282c

Reference yield:

: 82598-88-7
2,3,4,6-tetra-O-benzyl-D-mannono-1,5-lactone

: 887644-54-4
2-(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl)-L-(N-carbobenzyloxyl)-tryptophan methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: n-BuLi / tetrahydrofuran; hexane / -78 - 0 °C

1.2: 5.52 g / tetrahydrofuran; hexane / 3.5 h

2.1: Et₃SiH; BF₃*Et₂O / acetonitrile; CH₂Cl₂ / -40 °C

3.1: TBAF

4.1: PPh₃; Et₃N / Pd(OAc)2 / 60 °C

4.2: 74 percent / TBAF / tetrahydrofuran / 6 h / Heating

5.1: 49 percent / Sc(ClO₄)3; 5 Angstroem molecular sieves / CH₂Cl₂ / 0 °C

With triethylsilane; n-butyllithium; scandium(III) perchlorate; 5A molecular sieve; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; triethylamine; triphenylphosphine; palladium diacetate; In tetrahydrofuran; hexane; dichloromethane; acetonitrile;
DOI:10.1039/b516282c