(4S,5S,2'R)-5-<3'-azido-1'-<(tert-butyldimethylsilyl)oxy>-2'-propyl>-4-(cyclohexylmethyl)oxazolidin-2-one

Base Information

Chemical Name:(4S,5S,2'R)-5-<3'-azido-1'-<(tert-butyldimethylsilyl)oxy>-2'-propyl>-4-(cyclohexylmethyl)oxazolidin-2-one
CAS No.:120477-08-9
Molecular Formula:C₁₉H₃₆N₄O₃Si
Molecular Weight:396.605
Hs Code.:

Synonyms:(4S,5S,2'R)-5-<3'-azido-1'-<(tert-butyldimethylsilyl)oxy>-2'-propyl>-4-(cyclohexylmethyl)oxazolidin-2-one

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Chemical Property of (4S,5S,2'R)-5-<3'-azido-1'-<(tert-butyldimethylsilyl)oxy>-2'-propyl>-4-(cyclohexylmethyl)oxazolidin-2-one

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Technology Process of (4S,5S,2'R)-5-<3'-azido-1'-<(tert-butyldimethylsilyl)oxy>-2'-propyl>-4-(cyclohexylmethyl)oxazolidin-2-one

There total 8 articles about (4S,5S,2'R)-5-<3'-azido-1'-<(tert-butyldimethylsilyl)oxy>-2'-propyl>-4-(cyclohexylmethyl)oxazolidin-2-one 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%

: 120477-04-5
(4S,5S,2'S)-5-<1'-<(tert-butyldimethylsilyl)oxy>-3'-(methylsulfonoxy)-2'-propyl>-4-(cyclohexylmethyl)oxazolidin-2-one

: 120477-08-9
(4S,5S,2'R)-5-<3'-azido-1'-<(tert-butyldimethylsilyl)oxy>-2'-propyl>-4-(cyclohexylmethyl)oxazolidin-2-one

Guidance literature:: With sodium azide; In N,N-dimethyl-formamide; at 80 ℃; for 14h;
DOI:10.1021/jm00126a038

Reference yield:

: 98105-42-1
(S)-2-(t-butoxycarbonylamino)-3-cyclohexyl-1-propanal

: 120477-08-9
(4S,5S,2'R)-5-<3'-azido-1'-<(tert-butyldimethylsilyl)oxy>-2'-propyl>-4-(cyclohexylmethyl)oxazolidin-2-one

Guidance literature:: Multi-step reaction with 8 steps

1: 1) n-BuLi / 1) THF, hexane, -78 deg C, 1 h, 2) THF, -78 deg C, 1 h

2: 100 percent / NaH / dimethylformamide / Ambient temperature

3: 10percent aq. oxalic acid / CH₂Cl₂ / 1 h

4: NaBH₄ / CH₂Cl₂; methanol / 1 h / 0 °C

5: 91 percent / imidazole / dimethylformamide / 16 h / Ambient temperature

6: 1) BH₃, 2) 30percent H₂O₂, 3 M NaOH / 1) THF, r.t., 90 min, 2) H₂O, r.t., 90 min

7: 91 percent / diisopropylethylamine / CH₂Cl₂ / 1.5 h / 0 °C

8: 95 percent / NaN₃ / dimethylformamide / 14 h / 80 °C

With 1H-imidazole; sodium hydroxide; sodium tetrahydroborate; n-butyllithium; sodium azide; borane; dihydrogen peroxide; oxalic acid; sodium hydride; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jm00126a038

Reference yield:

: 120477-00-1
(4S,5S)-4-(cyclohexylmethyl)-5-(3'-hydroxy-2'-propenyl)oxazolidin-2-one

: 120477-08-9
(4S,5S,2'R)-5-<3'-azido-1'-<(tert-butyldimethylsilyl)oxy>-2'-propyl>-4-(cyclohexylmethyl)oxazolidin-2-one

Guidance literature:: Multi-step reaction with 4 steps

1: 91 percent / imidazole / dimethylformamide / 16 h / Ambient temperature

2: 1) BH₃, 2) 30percent H₂O₂, 3 M NaOH / 1) THF, r.t., 90 min, 2) H₂O, r.t., 90 min

3: 91 percent / diisopropylethylamine / CH₂Cl₂ / 1.5 h / 0 °C

4: 95 percent / NaN₃ / dimethylformamide / 14 h / 80 °C

With 1H-imidazole; sodium hydroxide; sodium azide; borane; dihydrogen peroxide; N-ethyl-N,N-diisopropylamine; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jm00126a038