N-Triphenylmethyl (3S)-3-{(2S,6R)-6-[(1S)-1-azido-2-phenylethyl]-2-methylmorpholin-3-one-4-yl}-4-(tert-butyldiphenylsilyloxy)butyramide

Base Information

Chemical Name:N-Triphenylmethyl (3S)-3-{(2S,6R)-6-[(1S)-1-azido-2-phenylethyl]-2-methylmorpholin-3-one-4-yl}-4-(tert-butyldiphenylsilyloxy)butyramide
CAS No.:245523-42-6
Molecular Formula:C₅₂H₅₅N₅O₄Si
Molecular Weight:842.125
Hs Code.:

Synonyms:N-Triphenylmethyl (3S)-3-{(2S,6R)-6-[(1S)-1-azido-2-phenylethyl]-2-methylmorpholin-3-one-4-yl}-4-(tert-butyldiphenylsilyloxy)butyramide

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Chemical Property of N-Triphenylmethyl (3S)-3-{(2S,6R)-6-[(1S)-1-azido-2-phenylethyl]-2-methylmorpholin-3-one-4-yl}-4-(tert-butyldiphenylsilyloxy)butyramide

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Technology Process of N-Triphenylmethyl (3S)-3-{(2S,6R)-6-[(1S)-1-azido-2-phenylethyl]-2-methylmorpholin-3-one-4-yl}-4-(tert-butyldiphenylsilyloxy)butyramide

There total 16 articles about N-Triphenylmethyl (3S)-3-{(2S,6R)-6-[(1S)-1-azido-2-phenylethyl]-2-methylmorpholin-3-one-4-yl}-4-(tert-butyldiphenylsilyloxy)butyramide 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: 84.0%

: 245523-41-5
N-Triphenylmethyl (3S)-3-{N'-[(2R,3S)-3-azido-2-hydroxy-4-phenylbutyl]-N'-[(1R)-1-bromoethylcarbonyl]amino}-4-(tert-butyldiphenylsilyloxy)butyramide

: 245523-42-6
N-Triphenylmethyl (3S)-3-{(2S,6R)-6-[(1S)-1-azido-2-phenylethyl]-2-methylmorpholin-3-one-4-yl}-4-(tert-butyldiphenylsilyloxy)butyramide

Guidance literature:: With potassium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; at 0 ℃; for 0.916667h;
DOI:10.1002/(SICI)1521-3765(19990802)5:8<2241::AID-CHEM2241>3.0.CO;2-L

Reference yield:

: 54966-42-6,1466-22-4
ethyl 3-benzylacrylate

: 245523-42-6
N-Triphenylmethyl (3S)-3-{(2S,6R)-6-[(1S)-1-azido-2-phenylethyl]-2-methylmorpholin-3-one-4-yl}-4-(tert-butyldiphenylsilyloxy)butyramide

Guidance literature:: Multi-step reaction with 10 steps

1: 81 percent / DIBAL-H / CH₂Cl₂ / 1 h / -78 °C

2: 87 percent / Ti(OiPr)4; tBuOOH; D-(-)-diethyl tartrate / CH₂Cl₂ / 24 h / -20 °C

3: 95 percent / Ti(OiPr)2(N₃)2 / benzene / 0.5 h / Heating

4: 92 percent / DMAP; pyridine / 2 h / 0 °C

5: 76 percent / NaH / dimethylformamide / 1 h / 0 °C

6: 72 percent / ethanol / 96 h / Heating

7: 95 percent / imidazole / CH₂Cl₂ / 4 h / 0 - 20 °C

8: DIC / CH₂Cl₂ / 4 h / 0 °C

9: HCl; H₂O / tetrahydrofuran / 96 h / 20 °C

10: 84 percent / KH / tetrahydrofuran; dimethylformamide / 0.92 h / 0 °C

With pyridine; 1H-imidazole; titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; dmap; diethyl (2S,3S)-tartrate; diisopropoxytitanium diazide; water; potassium hydride; sodium hydride; diisobutylaluminium hydride; dacarbazine; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; benzene; 1: Reduction / 2: Epoxidation / 3: Ring cleavage / 4: Tosylation / 5: Epoxidation / 6: Alkylation / 7: Etherification / 8: Acylation / 9: Hydrolysis / 10: Cyclization;
DOI:10.1002/(SICI)1521-3765(19990802)5:8<2241::AID-CHEM2241>3.0.CO;2-L

Reference yield:

: 42238-15-3,22910-59-4,49676-93-9
(2E)-4-phenylbut-2-en-1-ol

: 245523-42-6
N-Triphenylmethyl (3S)-3-{(2S,6R)-6-[(1S)-1-azido-2-phenylethyl]-2-methylmorpholin-3-one-4-yl}-4-(tert-butyldiphenylsilyloxy)butyramide

Guidance literature:: Multi-step reaction with 9 steps

1: 87 percent / Ti(OiPr)4; tBuOOH; D-(-)-diethyl tartrate / CH₂Cl₂ / 24 h / -20 °C

2: 95 percent / Ti(OiPr)2(N₃)2 / benzene / 0.5 h / Heating

3: 92 percent / DMAP; pyridine / 2 h / 0 °C

4: 76 percent / NaH / dimethylformamide / 1 h / 0 °C

5: 72 percent / ethanol / 96 h / Heating

6: 95 percent / imidazole / CH₂Cl₂ / 4 h / 0 - 20 °C

7: DIC / CH₂Cl₂ / 4 h / 0 °C

8: HCl; H₂O / tetrahydrofuran / 96 h / 20 °C

9: 84 percent / KH / tetrahydrofuran; dimethylformamide / 0.92 h / 0 °C

With pyridine; 1H-imidazole; titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; dmap; diethyl (2S,3S)-tartrate; diisopropoxytitanium diazide; water; potassium hydride; sodium hydride; dacarbazine; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; benzene; 1: Epoxidation / 2: Ring cleavage / 3: Tosylation / 4: Epoxidation / 5: Alkylation / 6: Etherification / 7: Acylation / 8: Hydrolysis / 9: Cyclization;
DOI:10.1002/(SICI)1521-3765(19990802)5:8<2241::AID-CHEM2241>3.0.CO;2-L