Technology Process of (2S,3S,4R)-3,4-O-isopropylidene-1-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-2-tetracosanoylamino-1,3,4-nonanetriol
There total 11 articles about (2S,3S,4R)-3,4-O-isopropylidene-1-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-2-tetracosanoylamino-1,3,4-nonanetriol 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:
- Guidance literature:
-
n-tetracosanoic acid;
With
benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride;
In
dichloromethane; N,N-dimethyl-formamide;
at 20 ℃;
for 0.5h;
(2S,3S,4R)-2-amino-3,4-O-isopropylidene-1-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-1,3,4-nonanetriol;
With
N-ethyl-N,N-diisopropylamine;
In
dichloromethane; N,N-dimethyl-formamide;
at 30 ℃;
for 16h;
DOI:10.1021/jo048151y
- Guidance literature:
-
Multi-step reaction with 11 steps
1.1: 91 percent / HCl / 18 h / 20 °C
2.1: 100 percent / Et3N; Bu2SnO / CH2Cl2 / 21 h / 20 °C
3.1: 91 percent / t-BuOK / tetrahydrofuran / 38 h / 20 °C
4.1: CuI / tetrahydrofuran; hexane / 0.5 h / -30 °C
4.2: 98 percent / tetrahydrofuran; hexane / 3 h / -20 °C
5.1: 93 percent / pyridine / 21 h / -40 - 20 °C
6.1: 100 percent / H2 / Pd(OH)2 / ethanol / 16 h / 20 °C / atmospheric pressure
7.1: 66 percent / NaN3 / dimethylformamide / 3 h / 95 °C
8.1: p-TsOH*H2O / 2 h / 20 °C
8.2: 75 percent / methanol / 1 h / 20 °C
9.1: 68 percent / Bu4NBr / toluene; dimethylformamide / 120 h / 20 °C
10.1: 100 percent / H2 / Pd/CaCO3 / ethanol / 16 h / 20 °C / atmospheric pressure
11.1: EDCI; HOBt / dimethylformamide; CH2Cl2 / 0.5 h / 20 °C
11.2: 89 percent / i-Pr2NEt / dimethylformamide; CH2Cl2 / 16 h / 30 °C
With
pyridine; hydrogenchloride; copper(l) iodide; sodium azide; potassium tert-butylate; tetrabutylammomium bromide; hydrogen; di(n-butyl)tin oxide; benzotriazol-1-ol; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine;
palladium dihydroxide; Lindlar's catalyst;
In
tetrahydrofuran; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo048151y
- Guidance literature:
-
Multi-step reaction with 9 steps
1.1: 91 percent / t-BuOK / tetrahydrofuran / 38 h / 20 °C
2.1: CuI / tetrahydrofuran; hexane / 0.5 h / -30 °C
2.2: 98 percent / tetrahydrofuran; hexane / 3 h / -20 °C
3.1: 93 percent / pyridine / 21 h / -40 - 20 °C
4.1: 100 percent / H2 / Pd(OH)2 / ethanol / 16 h / 20 °C / atmospheric pressure
5.1: 66 percent / NaN3 / dimethylformamide / 3 h / 95 °C
6.1: p-TsOH*H2O / 2 h / 20 °C
6.2: 75 percent / methanol / 1 h / 20 °C
7.1: 68 percent / Bu4NBr / toluene; dimethylformamide / 120 h / 20 °C
8.1: 100 percent / H2 / Pd/CaCO3 / ethanol / 16 h / 20 °C / atmospheric pressure
9.1: EDCI; HOBt / dimethylformamide; CH2Cl2 / 0.5 h / 20 °C
9.2: 89 percent / i-Pr2NEt / dimethylformamide; CH2Cl2 / 16 h / 30 °C
With
pyridine; copper(l) iodide; sodium azide; potassium tert-butylate; tetrabutylammomium bromide; hydrogen; benzotriazol-1-ol; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride;
palladium dihydroxide; Lindlar's catalyst;
In
tetrahydrofuran; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo048151y
