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

Base Information

• Chemical Name: N-Triphenylmethyl (3S)-3-{N'-[(2S,3S)-3-azido-2-hydroxy-4-phenylbutyl]-N'-[(1R)-1-bromoethylcarbonyl]amino}-4-(tert-butyldiphenylsilyloxy)butyramide
• CAS No.: 245523-27-7
• Molecular Formula: C₅₂H₅₆BrN₅O₄Si
• Molecular Weight: 923.037
• Mol file: 245523-27-7.mol

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

Chemical Property of N-Triphenylmethyl (3S)-3-{N'-[(2S,3S)-3-azido-2-hydroxy-4-phenylbutyl]-N'-[(1R)-1-bromoethylcarbonyl]amino}-4-(tert-butyldiphenylsilyloxy)butyramide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-Triphenylmethyl (3S)-3-{N'-[(2S,3S)-3-azido-2-hydroxy-4-phenylbutyl]-N'-[(1R)-1-bromoethylcarbonyl]amino}-4-(tert-butyldiphenylsilyloxy)butyramide

There total 16 articles about N-Triphenylmethyl (3S)-3-{N'-[(2S,3S)-3-azido-2-hydroxy-4-phenylbutyl]-N'-[(1R)-1-bromoethylcarbonyl]amino}-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:

(S)-3-[((2S,3S)-3-Azido-4-phenyl-2-triethylsilanyloxy-butyl)-((R)-2-bromo-propionyl)-amino]-4-(tert-butyl-diphenyl-silanyloxy)-N-trityl-butyramide → N-Triphenylmethyl (3S)-3-{N'-[(2S,3S)-3-azido-2-hydroxy-4-phenylbutyl]-N'-[(1R)-1-bromoethylcarbonyl]amino}-4-(tert-butyldiphenylsilyloxy)butyramide (245523-27-7)

Guidance literature:

With hydrogenchloride; water; In tetrahydrofuran; at 20 ℃; for 96h;

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-{N'-[(2S,3S)-3-azido-2-hydroxy-4-phenylbutyl]-N'-[(1R)-1-bromoethylcarbonyl]amino}-4-(tert-butyldiphenylsilyloxy)butyramide (245523-27-7)

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: 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

With 1H-imidazole; titanium(IV) isopropylate; 2,3,5-trimethyl-pyridine; hydrogenchloride; tert.-butylhydroperoxide; diethyl (2S,3S)-tartrate; diisopropoxytitanium diazide; water; sodium methylate; diisobutylaluminium hydride; dacarbazine; In tetrahydrofuran; ethanol; dichloromethane; benzene; 1: Reduction / 2: Epoxidation / 3: Ring cleavage / 4: Acylation / 5: Substitution / 6: Epoxidation / 7: Alkylation / 8: Etherification / 9: Acylation / 10: 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-{N'-[(2S,3S)-3-azido-2-hydroxy-4-phenylbutyl]-N'-[(1R)-1-bromoethylcarbonyl]amino}-4-(tert-butyldiphenylsilyloxy)butyramide (245523-27-7)

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: 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

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

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

upstream raw materials:

ethyl 3-benzylacrylate

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

L-Asn(Trt)

(2S,3S)-2-azido-1-phenyl-butane-3,4-diol

Downstream raw materials:

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

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