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

Base Information

Chemical Name:N-[(R)-3-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyloxy)-2-methylpropanoyl]-(adamant-2-yl)glycyl-L-alanyl-D-isoglutamine tert-butyl ester
CAS No.:1354546-15-8
Molecular Formula:C₆₂H₈₀N₄O₁₂
Molecular Weight:1073.34
Hs Code.:

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

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

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

There total 2 articles about N-[(R)-3-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyloxy)-2-methylpropanoyl]-(adamant-2-yl)glycyl-L-alanyl-D-isoglutamine tert-butyl 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: 76.0%

: 1190373-32-0
(R)-3-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyloxy)-2-methylpropanoic acid

: 1354546-12-5
(adamant-2-yl)glycyl-L-alanyl-D-isoglutamine tert-butyl ester

: 1354546-15-8
N-[(R)-3-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyloxy)-2-methylpropanoyl]-(adamant-2-yl)glycyl-L-alanyl-D-isoglutamine tert-butyl ester

Guidance literature:: (R)-3-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyloxy)-2-methylpropanoic acid; With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 0 ℃; for 0.5h;

(adamant-2-yl)glycyl-L-alanyl-D-isoglutamine tert-butyl ester; With triethylamine; In 1,4-dioxane; dichloromethane; at 0 - 20 ℃; for 49h;
DOI:10.5562/cca1827

Reference yield:

: 1354546-08-9
9-fluorenylmethyloxycarbonyl-(adamant-2-yl)glycine

: 1354546-15-8
N-[(R)-3-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyloxy)-2-methylpropanoyl]-(adamant-2-yl)glycyl-L-alanyl-D-isoglutamine tert-butyl ester

Guidance literature:: Multi-step reaction with 3 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

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