(2R,3S,4R)-N-benzyl-3-acetoxy-2-(4-methoxybenzyl)-4-<(tert-butyldimethylsilyl)oxy>pyrrolidine

Base Information

Chemical Name:(2R,3S,4R)-N-benzyl-3-acetoxy-2-(4-methoxybenzyl)-4-<(tert-butyldimethylsilyl)oxy>pyrrolidine
CAS No.:163592-88-9
Molecular Formula:C₂₇H₃₉NO₄Si
Molecular Weight:469.696
Hs Code.:

Synonyms:(2R,3S,4R)-N-benzyl-3-acetoxy-2-(4-methoxybenzyl)-4-<(tert-butyldimethylsilyl)oxy>pyrrolidine

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Chemical Property of (2R,3S,4R)-N-benzyl-3-acetoxy-2-(4-methoxybenzyl)-4-<(tert-butyldimethylsilyl)oxy>pyrrolidine

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Technology Process of (2R,3S,4R)-N-benzyl-3-acetoxy-2-(4-methoxybenzyl)-4-<(tert-butyldimethylsilyl)oxy>pyrrolidine

There total 13 articles about (2R,3S,4R)-N-benzyl-3-acetoxy-2-(4-methoxybenzyl)-4-<(tert-butyldimethylsilyl)oxy>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: 92.0%

: 108-24-7
acetic anhydride

: 163592-87-8
(2R,3S,4R)-N-benzyl-3-hydroxy-2-(4-methoxybenzyl)-4-<(tert-butyldimethylsilyl)oxy>pyrrolidine

: 163592-88-9
(2R,3S,4R)-N-benzyl-3-acetoxy-2-(4-methoxybenzyl)-4-<(tert-butyldimethylsilyl)oxy>pyrrolidine

Guidance literature:: With pyridine; for 48h; Ambient temperature;

Reference yield:

: 922-65-6
divinylcarbinol

: 163592-88-9
(2R,3S,4R)-N-benzyl-3-acetoxy-2-(4-methoxybenzyl)-4-<(tert-butyldimethylsilyl)oxy>pyrrolidine

Guidance literature:: Multi-step reaction with 12 steps

1: 1.) 4A molecular sieves, L-(+)-DIPT, TBHP, Ti(O-i-Pr)4, 2.) P(OEt)3, 3.) Ti(O-i-Pr)4

2: aq. NaHCO₃ / acetone / 3 h / Ambient temperature

3: 91.1 percent / PTS, NaHCO₃ / CH₂Cl₂

4: 74.9 percent / water, K₃Fe(CN)6, K₂CO₃, OsO₄ / 2-methyl-propan-2-ol / Ambient temperature

5: Et₃N / CH₂Cl₂ / 0 °C

6: K₂CO₃ / methanol / 0.33 h

7: 85.2 percent / CuI / tetrahydrofuran / -10 °C

8: DIBAL / toluene / 3 h / -78 °C

9: PPh₃, DEAD / CH₂Cl₂ / Ambient temperature

10: 80 percent / 2N aq. HCl / tetrahydrofuran

11: 89 percent / imidazole / dimethylformamide / 0.83 h / Ambient temperature

12: 92 percent / pyridine / 48 h / Ambient temperature

With pyridine; 1H-imidazole; titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; copper(l) iodide; osmium(VIII) oxide; L-(+)-diisopropyl tartrate; 4 A molecular sieve; water; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; triethylamine; triphenylphosphine; potassium hexacyanoferrate(III); diethylazodicarboxylate; triethyl phosphite; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol;

Reference yield:

: 123533-17-5
(2R,3S)-1-(benzylamino)pent-4-ene-2,3-diol

: 163592-88-9
(2R,3S,4R)-N-benzyl-3-acetoxy-2-(4-methoxybenzyl)-4-<(tert-butyldimethylsilyl)oxy>pyrrolidine

Guidance literature:: Multi-step reaction with 11 steps

1: aq. NaHCO₃ / acetone / 3 h / Ambient temperature

2: 91.1 percent / PTS, NaHCO₃ / CH₂Cl₂

3: 74.9 percent / water, K₃Fe(CN)6, K₂CO₃, OsO₄ / 2-methyl-propan-2-ol / Ambient temperature

4: Et₃N / CH₂Cl₂ / 0 °C

5: K₂CO₃ / methanol / 0.33 h

6: 85.2 percent / CuI / tetrahydrofuran / -10 °C

7: DIBAL / toluene / 3 h / -78 °C

8: PPh₃, DEAD / CH₂Cl₂ / Ambient temperature

9: 80 percent / 2N aq. HCl / tetrahydrofuran

10: 89 percent / imidazole / dimethylformamide / 0.83 h / Ambient temperature

11: 92 percent / pyridine / 48 h / Ambient temperature

With pyridine; 1H-imidazole; hydrogenchloride; copper(l) iodide; osmium(VIII) oxide; water; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; triethylamine; triphenylphosphine; potassium hexacyanoferrate(III); diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol;