N-[(R)-3-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyloxy)-2-methylpropanoyl]-(adamant-1-yl)glycyl-L-alanyl-D-isoglutamine

Base Information

Chemical Name:N-[(R)-3-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyloxy)-2-methylpropanoyl]-(adamant-1-yl)glycyl-L-alanyl-D-isoglutamine
CAS No.:1354546-17-0
Molecular Formula:C₅₈H₇₂N₄O₁₂
Molecular Weight:1017.23
Hs Code.:

Synonyms:N-[(R)-3-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyloxy)-2-methylpropanoyl]-(adamant-1-yl)glycyl-L-alanyl-D-isoglutamine

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Chemical Property of N-[(R)-3-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyloxy)-2-methylpropanoyl]-(adamant-1-yl)glycyl-L-alanyl-D-isoglutamine

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Technology Process of N-[(R)-3-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyloxy)-2-methylpropanoyl]-(adamant-1-yl)glycyl-L-alanyl-D-isoglutamine

There total 4 articles about N-[(R)-3-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyloxy)-2-methylpropanoyl]-(adamant-1-yl)glycyl-L-alanyl-D-isoglutamine 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: 65.0%

: 1354546-13-6
N-[(R)-3-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyloxy)-2-methylpropanoyl]-(adamant-1-yl)glycyl-L-alanyl-D-isoglutamine tert-butyl ester

: 1354546-17-0
N-[(R)-3-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyloxy)-2-methylpropanoyl]-(adamant-1-yl)glycyl-L-alanyl-D-isoglutamine

Guidance literature:: With trifluoroacetic acid; In water; at 20 ℃; for 2h;
DOI:10.5562/cca1827

Reference yield:

: 1354546-07-8
9-fluorenylmethyloxycarbonyl-(adamant-1-yl)glycine

: 1354546-17-0
N-[(R)-3-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyloxy)-2-methylpropanoyl]-(adamant-1-yl)glycyl-L-alanyl-D-isoglutamine

Guidance literature:: Multi-step reaction with 4 steps

1.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.5 h / 0 °C

1.2: 49 h / 0 - 20 °C

2.1: Octanethiol; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 16 h / 20 °C / Inert atmosphere

3.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.5 h / 0 °C

3.2: 49 h / 0 - 20 °C

4.1: trifluoroacetic acid / water / 2 h / 20 °C

With Octanethiol; benzotriazol-1-ol; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water;
DOI:10.5562/cca1827

Reference yield:

: 1354546-09-0
9-fluorenylmethyloxycarbonyl-(adamant-1-yl)glycyl-L-alanyl-D-isoglutamine tert-butyl ester

: 1354546-17-0
N-[(R)-3-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyloxy)-2-methylpropanoyl]-(adamant-1-yl)glycyl-L-alanyl-D-isoglutamine

Guidance literature:: Multi-step reaction with 3 steps

1.1: Octanethiol; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 16 h / 20 °C / Inert atmosphere

2.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.5 h / 0 °C

2.2: 49 h / 0 - 20 °C

3.1: trifluoroacetic acid / water / 2 h / 20 °C

With Octanethiol; benzotriazol-1-ol; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water;
DOI:10.5562/cca1827