(2S)-N-(adamant-1-yl)-3-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyloxy)-2-methylpropanamide

Base Information

Chemical Name:(2S)-N-(adamant-1-yl)-3-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyloxy)-2-methylpropanamide
CAS No.:1449303-93-8
Molecular Formula:C₄₈H₅₇NO₇
Molecular Weight:759.983
Hs Code.:

Synonyms:(2S)-N-(adamant-1-yl)-3-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyloxy)-2-methylpropanamide

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Chemical Property of (2S)-N-(adamant-1-yl)-3-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyloxy)-2-methylpropanamide

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Technology Process of (2S)-N-(adamant-1-yl)-3-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyloxy)-2-methylpropanamide

There total 3 articles about (2S)-N-(adamant-1-yl)-3-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyloxy)-2-methylpropanamide 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: 66.0%

: 1449303-89-2
(2S)-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyloxy)-2-methylpropionic acid

: 665-66-7,13878-11-0
amantadine hydrochloride

: 1449303-93-8
(2S)-N-(adamant-1-yl)-3-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyloxy)-2-methylpropanamide

Guidance literature:: (2S)-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyloxy)-2-methylpropionic acid; With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 0 ℃; for 0.5h;

amantadine hydrochloride; With benzotriazol-1-ol; In dichloromethane; water; at 0 - 20 ℃;
DOI:10.1016/j.tet.2013.06.097

Reference yield:

: C₃₆H₃₆Cl₃NO₆

: 1449303-93-8
(2S)-N-(adamant-1-yl)-3-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyloxy)-2-methylpropanamide

Guidance literature:: Multi-step reaction with 3 steps

1.1: boron trifluoride diethyl etherate / dichloromethane / 2.75 h / 0 °C / Inert atmosphere

2.1: sodium hydroxide / 1,4-dioxane / 24 h / 40 °C

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

3.2: 0 - 20 °C

With boron trifluoride diethyl etherate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; sodium hydroxide; In 1,4-dioxane; dichloromethane;
DOI:10.1016/j.tet.2013.06.097

Reference yield:

: 1449303-85-8
methyl (2S)-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyloxy)-2-methylpropionate

: 1449303-93-8
(2S)-N-(adamant-1-yl)-3-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyloxy)-2-methylpropanamide

Guidance literature:: Multi-step reaction with 2 steps

1.1: sodium hydroxide / 1,4-dioxane / 24 h / 40 °C

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

2.2: 0 - 20 °C

With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; sodium hydroxide; In 1,4-dioxane; dichloromethane;
DOI:10.1016/j.tet.2013.06.097