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

Base Information

• Chemical Name: N-Triphenylmethyl (3S)-3-{(2S,6S)-6-[(1S)-1-azido-2-phenylethyl]-2-methylmorpholin-3-one-4-yl}-4-hydroxybutyramide
• CAS No.: 245523-33-5
• Molecular Formula: C₃₆H₃₇N₅O₄
• Molecular Weight: 603.721
• Mol file: 245523-33-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 17 articles about N-Triphenylmethyl (3S)-3-{(2S,6S)-6-[(1S)-1-azido-2-phenylethyl]-2-methylmorpholin-3-one-4-yl}-4-hydroxybutyramide 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: 98.0%

N-Triphenylmethyl (3S)-3-{(2S,6S)-6-[(1S)-1-azido-2-phenylethyl]-2-methylmorpholin-3-one-4-yl}-4-(tert-butyldiphenylsilyloxy)butyramide (245523-30-2) → N-Triphenylmethyl (3S)-3-{(2S,6S)-6-[(1S)-1-azido-2-phenylethyl]-2-methylmorpholin-3-one-4-yl}-4-hydroxybutyramide (245523-33-5)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1002/(SICI)1521-3765(19990802)5:8<2241::AID-CHEM2241>3.0.CO;2-L

Reference yield:

ethyl 3-benzylacrylate (54966-42-6,1466-22-4) → N-Triphenylmethyl (3S)-3-{(2S,6S)-6-[(1S)-1-azido-2-phenylethyl]-2-methylmorpholin-3-one-4-yl}-4-hydroxybutyramide (245523-33-5)

Guidance literature:

Multi-step reaction with 12 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: collidine / CH₂Cl₂ / 18 h / -78 - 20 °C

5: CH₂Cl₂ / 24 h / 0 - 20 °C

6: 80 percent / NaOMe / tetrahydrofuran / 0.25 h / 20 °C

7: 66 percent / ethanol / 96 h / Heating

8: 91 percent / imidazole / CH₂Cl₂ / 4 h / 0 - 20 °C

9: DIC / CH₂Cl₂ / 4 h / 0 °C

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

11: 84 percent / KH / tetrahydrofuran; dimethylformamide / 0.92 h / 0 °C

12: 98 percent / TBAF hydrate / tetrahydrofuran / 2 h / 20 °C

With 1H-imidazole; titanium(IV) isopropylate; 2,3,5-trimethyl-pyridine; hydrogenchloride; tert.-butylhydroperoxide; diethyl (2S,3S)-tartrate; diisopropoxytitanium diazide; tetrabutyl ammonium fluoride; water; sodium methylate; potassium hydride; diisobutylaluminium hydride; dacarbazine; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; benzene; 1: Reduction / 2: Epoxidation / 3: Ring cleavage / 4: Acylation / 5: Substitution / 6: Epoxidation / 7: Alkylation / 8: Etherification / 9: Acylation / 10: Hydrolysis / 11: Cyclization / 12: Hydrolysis;

DOI:10.1002/(SICI)1521-3765(19990802)5:8<2241::AID-CHEM2241>3.0.CO;2-L

Reference yield:

(2E)-4-phenylbut-2-en-1-ol (42238-15-3,22910-59-4,49676-93-9) → N-Triphenylmethyl (3S)-3-{(2S,6S)-6-[(1S)-1-azido-2-phenylethyl]-2-methylmorpholin-3-one-4-yl}-4-hydroxybutyramide (245523-33-5)

Guidance literature:

Multi-step reaction with 11 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: collidine / CH₂Cl₂ / 18 h / -78 - 20 °C

4: CH₂Cl₂ / 24 h / 0 - 20 °C

5: 80 percent / NaOMe / tetrahydrofuran / 0.25 h / 20 °C

6: 66 percent / ethanol / 96 h / Heating

7: 91 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

11: 98 percent / TBAF hydrate / tetrahydrofuran / 2 h / 20 °C

With 1H-imidazole; titanium(IV) isopropylate; 2,3,5-trimethyl-pyridine; hydrogenchloride; tert.-butylhydroperoxide; diethyl (2S,3S)-tartrate; diisopropoxytitanium diazide; tetrabutyl ammonium fluoride; water; sodium methylate; potassium hydride; dacarbazine; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; benzene; 1: Epoxidation / 2: Ring cleavage / 3: Acylation / 4: Substitution / 5: Epoxidation / 6: Alkylation / 7: Etherification / 8: Acylation / 9: Hydrolysis / 10: Cyclization / 11: Hydrolysis;

DOI:10.1002/(SICI)1521-3765(19990802)5:8<2241::AID-CHEM2241>3.0.CO;2-L

upstream raw materials:

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

ethyl 3-benzylacrylate

(2E)-4-phenylbut-2-en-1-ol

L-Asn(Trt)