N-Triphenylmethyl (3S)-3-[(2R,3S)-3-azido-4-phenyl-2-triethylsilyloxybutylamino]-4-(tert-butyldiphenylsilyloxy)butyramide

Base Information

Chemical Name:N-Triphenylmethyl (3S)-3-[(2R,3S)-3-azido-4-phenyl-2-triethylsilyloxybutylamino]-4-(tert-butyldiphenylsilyloxy)butyramide
CAS No.:245523-40-4
Molecular Formula:C₅₅H₆₇N₅O₃Si₂
Molecular Weight:902.34
Hs Code.:

Synonyms:N-Triphenylmethyl (3S)-3-[(2R,3S)-3-azido-4-phenyl-2-triethylsilyloxybutylamino]-4-(tert-butyldiphenylsilyloxy)butyramide

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of N-Triphenylmethyl (3S)-3-[(2R,3S)-3-azido-4-phenyl-2-triethylsilyloxybutylamino]-4-(tert-butyldiphenylsilyloxy)butyramide

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Technology Process of N-Triphenylmethyl (3S)-3-[(2R,3S)-3-azido-4-phenyl-2-triethylsilyloxybutylamino]-4-(tert-butyldiphenylsilyloxy)butyramide

There total 13 articles about N-Triphenylmethyl (3S)-3-[(2R,3S)-3-azido-4-phenyl-2-triethylsilyloxybutylamino]-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: 95.0%

: 994-30-9
triethylsilyl chloride

: 245523-39-1
N-Triphenylmethyl (3S)-3-[(2R,3S)-3-azido-2-hydroxy-4-phenylbutylamino]-4-(tert-butyldiphenylsilyloxy)butyramide

: 245523-40-4
N-Triphenylmethyl (3S)-3-[(2R,3S)-3-azido-4-phenyl-2-triethylsilyloxybutylamino]-4-(tert-butyldiphenylsilyloxy)butyramide

Guidance literature:: With 1H-imidazole; In dichloromethane; at 0 - 20 ℃; for 4h;
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

: 245523-40-4
N-Triphenylmethyl (3S)-3-[(2R,3S)-3-azido-4-phenyl-2-triethylsilyloxybutylamino]-4-(tert-butyldiphenylsilyloxy)butyramide

Guidance literature:: Multi-step reaction with 7 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

With pyridine; 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; diethyl (2S,3S)-tartrate; diisopropoxytitanium diazide; sodium hydride; diisobutylaluminium hydride; In ethanol; dichloromethane; N,N-dimethyl-formamide; benzene; 1: Reduction / 2: Epoxidation / 3: Ring cleavage / 4: Tosylation / 5: Epoxidation / 6: Alkylation / 7: Etherification;
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

: 245523-40-4
N-Triphenylmethyl (3S)-3-[(2R,3S)-3-azido-4-phenyl-2-triethylsilyloxybutylamino]-4-(tert-butyldiphenylsilyloxy)butyramide

Guidance literature:: Multi-step reaction with 6 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

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