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

Base Information

Chemical Name:N-Triphenylmethyl (3S)-3-[(2R,3S)-3-azido-2-hydroxy-4-phenylbutylamino]-4-(tert-butyldiphenylsilyloxy)butyramide
CAS No.:245523-39-1
Molecular Formula:C₄₉H₅₃N₅O₃Si
Molecular Weight:788.077
Hs Code.:

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

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

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

There total 11 articles about N-Triphenylmethyl (3S)-3-[(2R,3S)-3-azido-2-hydroxy-4-phenylbutylamino]-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: 72.0%

: 136465-89-9
(2S)-2-[1'(S)-1-azido-2-phenylethyl]oxirane

: 245523-23-3
N-Triphenylmethyl (3S)-3-amino-4-(tert-butyldiphenylsilyloxy)butyramide

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

Guidance literature:: In ethanol; for 96h; Heating;
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

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

Guidance literature:: Multi-step reaction with 6 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

With pyridine; 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;
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

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

Guidance literature:: Multi-step reaction with 5 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

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