(2S,3S,4S,5S)-N-<(Benzyloxy)carbonyl>-5-butyl-3,4-dihydroxy-2-(4-pentenyl)pyrrolidine

Base Information

Chemical Name:(2S,3S,4S,5S)-N-<(Benzyloxy)carbonyl>-5-butyl-3,4-dihydroxy-2-(4-pentenyl)pyrrolidine
CAS No.:118014-70-3
Molecular Formula:C₂₁H₃₁NO₄
Molecular Weight:361.481
Hs Code.:

Synonyms:(2S,3S,4S,5S)-N-<(Benzyloxy)carbonyl>-5-butyl-3,4-dihydroxy-2-(4-pentenyl)pyrrolidine

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Chemical Property of (2S,3S,4S,5S)-N-<(Benzyloxy)carbonyl>-5-butyl-3,4-dihydroxy-2-(4-pentenyl)pyrrolidine

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Technology Process of (2S,3S,4S,5S)-N-<(Benzyloxy)carbonyl>-5-butyl-3,4-dihydroxy-2-(4-pentenyl)pyrrolidine

There total 13 articles about (2S,3S,4S,5S)-N-<(Benzyloxy)carbonyl>-5-butyl-3,4-dihydroxy-2-(4-pentenyl)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: 84.0%

: 117941-16-9
(2S,3S,4S,5S)-N-<(Benzyloxy)carbonyl>-5-butyl-3,4-bis<(methoxymethyl)oxy>-2-(4-pentenyl)pyrrolidine

: 118014-70-3
(2S,3S,4S,5S)-N-<(Benzyloxy)carbonyl>-5-butyl-3,4-dihydroxy-2-(4-pentenyl)pyrrolidine

Guidance literature:: With hydrogenchloride; In methanol; for 0.5h; Heating;
DOI:10.1021/ja00186a038

Reference yield:

: 117941-00-1
(2S,3R)-1-(Benzyloxy)-2,3-bis<(methoxymethyl)oxy>octan-4-one

: 118014-70-3
(2S,3S,4S,5S)-N-<(Benzyloxy)carbonyl>-5-butyl-3,4-dihydroxy-2-(4-pentenyl)pyrrolidine

Guidance literature:: Multi-step reaction with 12 steps

1: 75 percent / 1 M LiBH(sec-Bu)3 / tetrahydrofuran / 1 h / -78 °C

2: 51 percent / triphenyl phosphine, diethyl azodicarboxylate / tetrahydrofuran / 14 h / Ambient temperature

3: 76 percent / H₂ / 10percent Pd/C / methanol / 3 h

4: 86 percent / oxalyl chloride, dimethyl sulfoxide / CH₂Cl₂ / 1 h / -78 °C

5: 1.) Mg / 1.) THF, 2.) THF, -78 deg C, 30 min

6: hydrazine hydrate / ethanol / 2 h / Heating

7: aq. Na₂CO₃ / CH₂Cl₂ / 0.08 h / 0 °C

8: 80 percent / oxalyl chloride, dimethyl sulfoxide / CH₂Cl₂ / 1 h / -78 °C

9: 0.14 M Zn(BH₄)2 / diethyl ether / 0.75 h / 0 °C

10: triethylamine / CH₂Cl₂ / 0.17 h / 0 °C

11: t-BuOK / tetrahydrofuran / 1.) 0 deg C, 10 min, 2.) room temp., 10 min

12: 84 percent / concentrated HCl / methanol / 0.5 h / Heating

With hydrogenchloride; zinc(II) tetrahydroborate; oxalyl dichloride; potassium tert-butylate; hydrogen; L-Selectride; sodium carbonate; hydrazine hydrate; magnesium; dimethyl sulfoxide; triethylamine; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane;
DOI:10.1021/ja00186a038

Reference yield:

: 117941-01-2,118014-58-7
(2S,3S)-1-Benzyloxy-2,3-bis-methoxymethoxy-octan-4-ol

: 118014-70-3
(2S,3S,4S,5S)-N-<(Benzyloxy)carbonyl>-5-butyl-3,4-dihydroxy-2-(4-pentenyl)pyrrolidine

Guidance literature:: Multi-step reaction with 13 steps

1: 95 percent / oxalyl chloride, dimethyl sulfoxide / CH₂Cl₂ / 1 h / -78 °C

2: 75 percent / 1 M LiBH(sec-Bu)3 / tetrahydrofuran / 1 h / -78 °C

3: 51 percent / triphenyl phosphine, diethyl azodicarboxylate / tetrahydrofuran / 14 h / Ambient temperature

4: 76 percent / H₂ / 10percent Pd/C / methanol / 3 h

5: 86 percent / oxalyl chloride, dimethyl sulfoxide / CH₂Cl₂ / 1 h / -78 °C

6: 1.) Mg / 1.) THF, 2.) THF, -78 deg C, 30 min

7: hydrazine hydrate / ethanol / 2 h / Heating

8: aq. Na₂CO₃ / CH₂Cl₂ / 0.08 h / 0 °C

9: 80 percent / oxalyl chloride, dimethyl sulfoxide / CH₂Cl₂ / 1 h / -78 °C

10: 0.14 M Zn(BH₄)2 / diethyl ether / 0.75 h / 0 °C

11: triethylamine / CH₂Cl₂ / 0.17 h / 0 °C

12: t-BuOK / tetrahydrofuran / 1.) 0 deg C, 10 min, 2.) room temp., 10 min

13: 84 percent / concentrated HCl / methanol / 0.5 h / Heating

With hydrogenchloride; zinc(II) tetrahydroborate; oxalyl dichloride; potassium tert-butylate; hydrogen; L-Selectride; sodium carbonate; hydrazine hydrate; magnesium; dimethyl sulfoxide; triethylamine; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane;
DOI:10.1021/ja00186a038