- The total chemical synthesis of the monoglycosylated GM2 ganglioside activator using a novel cysteine surrogateBy Sato, Kohei et al, Chemical Communications (Cambridge, 2015, 51(49), 9946-9948
Cas no 170943-10-9 (L-Aspartic acid, N-[(1,1-dimethylethoxy)carbonyl]-, 1-methyl 4-(2-propen-1-yl) ester)
170943-10-9 structure
Product Name:L-Aspartic acid, N-[(1,1-dimethylethoxy)carbonyl]-, 1-methyl 4-(2-propen-1-yl) ester
CAS No:170943-10-9
MF:C13H21NO6
MW:287.30894446373
CID:5597179
Update Time:2023-08-23
L-Aspartic acid, N-[(1,1-dimethylethoxy)carbonyl]-, 1-methyl 4-(2-propen-1-yl) ester Chemical and Physical Properties
Names and Identifiers
-
- L-Aspartic acid, N-[(1,1-dimethylethoxy)carbonyl]-, 1-methyl 4-(2-propenyl) ester (9CI)
- 1-Methyl 4-(2-propen-1-yl) N-[(1,1-dimethylethoxy)carbonyl]-L-aspartate
- L-Aspartic acid, N-[(1,1-dimethylethoxy)carbonyl]-, 1-methyl 4-(2-propen-1-yl) ester
-
- Inchi: 1S/C13H21NO6/c1-6-7-19-10(15)8-9(11(16)18-5)14-12(17)20-13(2,3)4/h6,9H,1,7-8H2,2-5H3,(H,14,17)/t9-/m0/s1
- InChI Key: KYKNNIMLGUGDHF-VIFPVBQESA-N
- SMILES: O(C(=O)N[C@@H](CC(=O)OCC=C)C(OC)=O)C(C)(C)C
L-Aspartic acid, N-[(1,1-dimethylethoxy)carbonyl]-, 1-methyl 4-(2-propen-1-yl) ester Production Method
Production Method 1
Reaction Conditions
1.1R:AcCl, 15 min, rt
1.21 h, rt; 23 h, rt
2.1R:Et3N, S:H2O, S:Dioxane, 3 h, rt
2.2R:Citric acid, S:H2O, rt, pH 4-5
3.1R:K2CO3, S:DMF, 2 h, rt
3.212 h, rt
1.21 h, rt; 23 h, rt
2.1R:Et3N, S:H2O, S:Dioxane, 3 h, rt
2.2R:Citric acid, S:H2O, rt, pH 4-5
3.1R:K2CO3, S:DMF, 2 h, rt
3.212 h, rt
Reference
Production Method 2
Reaction Conditions
1.1R:AcCl, S:CH2=CHCH2OH, 0°C; 15 min, 0°C; 1 h, rt
1.218 h, rt; rt → 0°C
1.3S:Et2O, 1 h, 0°C
2.1R:Et3N, S:H2O, S:Dioxane, rt; 22 h, rt
2.2R:Citric acid, S:H2O, 0°C, pH 3
3.1R:K2CO3, S:DMF, 30 s, 0°C; 24 h, 0°C
3.2S:H2O, 0°C
1.218 h, rt; rt → 0°C
1.3S:Et2O, 1 h, 0°C
2.1R:Et3N, S:H2O, S:Dioxane, rt; 22 h, rt
2.2R:Citric acid, S:H2O, 0°C, pH 3
3.1R:K2CO3, S:DMF, 30 s, 0°C; 24 h, 0°C
3.2S:H2O, 0°C
Reference
- Thiazolidine-Protected β-Thiol Asparagine: Applications in One-Pot Ligation-Desulfurization ChemistryBy Sayers, Jessica et al, Organic Letters, 2015, 17(19), 4902-4905
L-Aspartic acid, N-[(1,1-dimethylethoxy)carbonyl]-, 1-methyl 4-(2-propen-1-yl) ester Raw materials
L-Aspartic acid, N-[(1,1-dimethylethoxy)carbonyl]-, 1-methyl 4-(2-propen-1-yl) ester Preparation Products
L-Aspartic acid, N-[(1,1-dimethylethoxy)carbonyl]-, 1-methyl 4-(2-propen-1-yl) ester Related Literature
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Huiying Xu,Lu Zheng,Yu Zhou,Bang-Ce Ye Analyst, 2021,146, 5542-5549
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Hamid Heydari,Mohammad B. Gholivand New J. Chem., 2017,41, 237-244
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Kanjun Sun,Fengting Hua,Shuzhen Cui,Yanrong Zhu,Hui Peng,Guofu Ma RSC Adv., 2021,11, 37631-37642
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Muniyandi Sankaralingam,So Hyun Jeon,Yong-Min Lee,Mi Sook Seo,Wonwoo Nam Dalton Trans., 2016,45, 376-383
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