(2S,4S)-2-Butyl-4-pent-4-enyl-6-oxa-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid benzyl ester

Base Information

Chemical Name:(2S,4S)-2-Butyl-4-pent-4-enyl-6-oxa-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid benzyl ester
CAS No.:119814-57-2
Molecular Formula:C₂₁H₂₉NO₃
Molecular Weight:343.466
Hs Code.:

Synonyms:(2S,4S)-2-Butyl-4-pent-4-enyl-6-oxa-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid benzyl ester

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Chemical Property of (2S,4S)-2-Butyl-4-pent-4-enyl-6-oxa-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid benzyl ester

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Technology Process of (2S,4S)-2-Butyl-4-pent-4-enyl-6-oxa-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid benzyl ester

There total 43 articles about (2S,4S)-2-Butyl-4-pent-4-enyl-6-oxa-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid benzyl ester 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:

: 117941-01-2
(2S,3S,4S)-1-(Benzyloxy)-2,3-bis<(methoxymethyl)oxy>octan-4-ol

: 119814-57-2
(2R,4R)-2-Butyl-4-pent-4-enyl-6-oxa-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 12 steps

1: 61 percent / triphenylphosphine, diethyl azodicarboxylate / tetrahydrofuran / 14 h / Ambient temperature

2: 71 percent / H₂ / 10percent Pd/C / methanol / 3 h

3: 94 percent / oxalyl chloride, dimethyl sulfoxide / CH₂Cl₂ / 1 h / -78 °C

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

5: 85 percent / oxalyl chloride, dimethyl sulfoxide / CH₂Cl₂ / 1 h / -78 °C

6: 68 percent / 0.14 M Zn(BH₄)2 / diethyl ether / 0.75 h / 0 °C

7: hydrazine hydrate / ethanol / 2 h / Heating

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

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

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

11: 95 percent / concentrated HCl / methanol / 0.5 h / Heating

12: triphenylphosphine, imidazole, 2,4,5-triiodoimidazole, zinc dust / toluene / 0.5 h / Heating

With 1H-imidazole; hydrogenchloride; 2,4,5-triiodoimidazole; zinc(II) tetrahydroborate; oxalyl dichloride; potassium tert-butylate; hydrogen; sodium carbonate; hydrazine hydrate; magnesium; dimethyl sulfoxide; triethylamine; triphenylphosphine; zinc; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; toluene;
DOI:10.1021/ja00186a038

Reference yield:

: 117941-07-8
(2S,3S,4R)-1-(Benzyloxy)-4-(1,3-dioxo-2-azaindan-2-yl)-2,3-bis<(methoxymethyl)oxy>octane

: 119814-57-2
(2R,4R)-2-Butyl-4-pent-4-enyl-6-oxa-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 11 steps

1: 71 percent / H₂ / 10percent Pd/C / methanol / 3 h

2: 94 percent / oxalyl chloride, dimethyl sulfoxide / CH₂Cl₂ / 1 h / -78 °C

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

4: 85 percent / oxalyl chloride, dimethyl sulfoxide / CH₂Cl₂ / 1 h / -78 °C

5: 68 percent / 0.14 M Zn(BH₄)2 / diethyl ether / 0.75 h / 0 °C

6: hydrazine hydrate / ethanol / 2 h / Heating

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

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

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

10: 95 percent / concentrated HCl / methanol / 0.5 h / Heating

11: triphenylphosphine, imidazole, 2,4,5-triiodoimidazole, zinc dust / toluene / 0.5 h / Heating

With 1H-imidazole; hydrogenchloride; 2,4,5-triiodoimidazole; zinc(II) tetrahydroborate; oxalyl dichloride; potassium tert-butylate; hydrogen; sodium carbonate; hydrazine hydrate; magnesium; dimethyl sulfoxide; triethylamine; triphenylphosphine; zinc; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; toluene;
DOI:10.1021/ja00186a038

Reference yield:

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

: 119814-57-2
(2R,4R)-2-Butyl-4-pent-4-enyl-6-oxa-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 13 steps

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

2: 61 percent / triphenylphosphine, diethyl azodicarboxylate / tetrahydrofuran / 14 h / Ambient temperature

3: 71 percent / H₂ / 10percent Pd/C / methanol / 3 h

4: 94 percent / oxalyl chloride, dimethyl sulfoxide / CH₂Cl₂ / 1 h / -78 °C

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

6: 85 percent / oxalyl chloride, dimethyl sulfoxide / CH₂Cl₂ / 1 h / -78 °C

7: 68 percent / 0.14 M Zn(BH₄)2 / diethyl ether / 0.75 h / 0 °C

8: hydrazine hydrate / ethanol / 2 h / Heating

9: aq. Na₂CO₃ / CH₂Cl₂ / 0.08 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: 95 percent / concentrated HCl / methanol / 0.5 h / Heating

13: triphenylphosphine, imidazole, 2,4,5-triiodoimidazole, zinc dust / toluene / 0.5 h / Heating

With 1H-imidazole; hydrogenchloride; 2,4,5-triiodoimidazole; zinc(II) tetrahydroborate; oxalyl dichloride; potassium tert-butylate; hydrogen; L-Selectride; sodium carbonate; hydrazine hydrate; magnesium; dimethyl sulfoxide; triethylamine; triphenylphosphine; zinc; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; toluene;
DOI:10.1021/ja00186a038