(2''S)-1-(2''-tert-butoxycarbonylamino-2''-carboxy-ethyl)-4-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)-1H-[1,2,3]triazole

Base Information

Chemical Name:(2''S)-1-(2''-tert-butoxycarbonylamino-2''-carboxy-ethyl)-4-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)-1H-[1,2,3]triazole
CAS No.:763139-37-3
Molecular Formula:C₄₄H₅₀N₄O₉
Molecular Weight:778.902
Hs Code.:

Synonyms:(2''S)-1-(2''-tert-butoxycarbonylamino-2''-carboxy-ethyl)-4-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)-1H-[1,2,3]triazole

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Chemical Property of (2''S)-1-(2''-tert-butoxycarbonylamino-2''-carboxy-ethyl)-4-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)-1H-[1,2,3]triazole

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Technology Process of (2''S)-1-(2''-tert-butoxycarbonylamino-2''-carboxy-ethyl)-4-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)-1H-[1,2,3]triazole

There total 5 articles about (2''S)-1-(2''-tert-butoxycarbonylamino-2''-carboxy-ethyl)-4-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)-1H-[1,2,3]triazole 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: 70.0%

: 122225-54-1,108283-49-4
(S)-3-azido-2-((tert-butoxycarbonyl)amino)propanoic acid

: 168253-07-4
(2R,3R,4R,5S,6S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-ethynyl-tetrahydro-pyran

: 763139-37-3
(2''S)-1-(2''-tert-butoxycarbonylamino-2''-carboxy-ethyl)-4-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)-1H-[1,2,3]triazole

Guidance literature:: With copper diacetate; sodium L-ascorbate; In water; tert-butyl alcohol; at 20 ℃; for 16h;
DOI:10.1021/ol048841o

Reference yield:

: 763122-86-7
(2''S)-1-(2''-tert-butoxycarbonylamino-3''-hydroxy-propyl)-4-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)-1H-[1,2,3]triazole

: 763139-37-3
(2''S)-1-(2''-tert-butoxycarbonylamino-2''-carboxy-ethyl)-4-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)-1H-[1,2,3]triazole

Guidance literature:: With jones' reagent; In acetone; at 0 - 20 ℃; for 3.5h;
DOI:10.1021/ol048963g

Reference yield:

: 108149-63-9,108149-65-1
tert-butyl (4S)-4-(hydroxymethyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

: 763139-37-3
(2''S)-1-(2''-tert-butoxycarbonylamino-2''-carboxy-ethyl)-4-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)-1H-[1,2,3]triazole

Guidance literature:: Multi-step reaction with 4 steps

1.1: diphenylphosphoryl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene / dimethylformamide / 12 h / 100 °C

1.2: 70 percent / NaN₃ / dimethylformamide / 2 h / 100 °C

2.1: 32 percent / 14 h / 120 °C

3.1: 67 percent / p-TsOH*H₂O / methanol / 72 h / 20 °C

4.1: Jones' reagent / acetone / 3.5 h / 0 - 20 °C

With jones' reagent; diphenylphosphoranyl azide; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; N,N-dimethyl-formamide; acetone;
DOI:10.1021/ol048963g