(2S,3S)-N-(benzyloxycarbonyl)-2-<(tert-butyldimethylsiloxy)methyl>-3-(tert-butyldiphenylsiloxy)pyrrolidine

Base Information

Chemical Name:(2S,3S)-N-(benzyloxycarbonyl)-2-<(tert-butyldimethylsiloxy)methyl>-3-(tert-butyldiphenylsiloxy)pyrrolidine
CAS No.:174221-97-7
Molecular Formula:C₃₅H₄₉NO₄Si₂
Molecular Weight:603.949
Hs Code.:

Synonyms:(2S,3S)-N-(benzyloxycarbonyl)-2-<(tert-butyldimethylsiloxy)methyl>-3-(tert-butyldiphenylsiloxy)pyrrolidine

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Chemical Property of (2S,3S)-N-(benzyloxycarbonyl)-2-<(tert-butyldimethylsiloxy)methyl>-3-(tert-butyldiphenylsiloxy)pyrrolidine

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Technology Process of (2S,3S)-N-(benzyloxycarbonyl)-2-<(tert-butyldimethylsiloxy)methyl>-3-(tert-butyldiphenylsiloxy)pyrrolidine

There total 9 articles about (2S,3S)-N-(benzyloxycarbonyl)-2-<(tert-butyldimethylsiloxy)methyl>-3-(tert-butyldiphenylsiloxy)pyrrolidine 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%

: 501-53-1,94274-21-2
benzyl chloroformate

: 174222-02-7
(2S,3S)-2-<(tert-butyldimethylsiloxy)methyl>-3-(tert-butyldiphenylsiloxy)pyrrolidine

: 174221-97-7
(2S,3S)-N-(benzyloxycarbonyl)-2-<(tert-butyldimethylsiloxy)methyl>-3-(tert-butyldiphenylsiloxy)pyrrolidine

Guidance literature:: With potassium carbonate; In tetrahydrofuran; water; at 0 ℃; for 2h;
DOI:10.1021/jo951444u

Reference yield:

: 125827-92-1
(2R,3S)-3-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidenepentane-1,2,3,5-tetrol

: 174221-97-7
(2S,3S)-N-(benzyloxycarbonyl)-2-<(tert-butyldimethylsiloxy)methyl>-3-(tert-butyldiphenylsiloxy)pyrrolidine

Guidance literature:: Multi-step reaction with 7 steps

1: pyridine / 9 h / Ambient temperature

2: NaN₃ / dimethylformamide / 12 h / 65 °C

3: 96 percent / aq. HOAc / 24 h / Ambient temperature

4: 89 percent / imidazole, DMAP / tetrahydrofuran / 24 h / Ambient temperature

5: 98 percent / pyridine / 9 h / Ambient temperature

6: 1.) PPh₃, 2.) aq. NaOH / 1.) THF, room temperature, 7 h, 2.) reflux, 36 h

7: 95 percent / K₂CO₃ / tetrahydrofuran; H₂O / 2 h / 0 °C

With pyridine; 1H-imidazole; dmap; sodium hydroxide; sodium azide; potassium carbonate; acetic acid; triphenylphosphine; In tetrahydrofuran; water; N,N-dimethyl-formamide;
DOI:10.1021/jo951444u

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 174221-97-7
(2S,3S)-N-(benzyloxycarbonyl)-2-<(tert-butyldimethylsiloxy)methyl>-3-(tert-butyldiphenylsiloxy)pyrrolidine

Guidance literature:: Multi-step reaction with 9 steps

1: 98 percent / imidazole, DMAP / dimethylformamide / 24 h / Ambient temperature

2: 1.) O₃, 2.) NaBH₄ / 1.) MeOH, -78 deg C, 2.) room temperature

3: pyridine / 9 h / Ambient temperature

4: NaN₃ / dimethylformamide / 12 h / 65 °C

5: 96 percent / aq. HOAc / 24 h / Ambient temperature

6: 89 percent / imidazole, DMAP / tetrahydrofuran / 24 h / Ambient temperature

7: 98 percent / pyridine / 9 h / Ambient temperature

8: 1.) PPh₃, 2.) aq. NaOH / 1.) THF, room temperature, 7 h, 2.) reflux, 36 h

9: 95 percent / K₂CO₃ / tetrahydrofuran; H₂O / 2 h / 0 °C

With pyridine; 1H-imidazole; dmap; sodium hydroxide; sodium tetrahydroborate; sodium azide; potassium carbonate; ozone; acetic acid; triphenylphosphine; In tetrahydrofuran; water; N,N-dimethyl-formamide;
DOI:10.1021/jo951444u