D-1-[6-(N,N-dibenzylamino)-6-(benzyloxycarbonyl)]-transhex-2-enoyl-3-amino-1,1,1-trifluorobutan-2-one

Base Information

• Chemical Name: D-1-[6-(N,N-dibenzylamino)-6-(benzyloxycarbonyl)]-transhex-2-enoyl-3-amino-1,1,1-trifluorobutan-2-one
• CAS No.: 1427207-10-0
• Molecular Formula: C₃₂H₃₃F₃N₂O₄
• Molecular Weight: 566.62

Synonyms:D-1-[6-(N,N-dibenzylamino)-6-(benzyloxycarbonyl)]-transhex-2-enoyl-3-amino-1,1,1-trifluorobutan-2-one

Chemical Property of D-1-[6-(N,N-dibenzylamino)-6-(benzyloxycarbonyl)]-transhex-2-enoyl-3-amino-1,1,1-trifluorobutan-2-one

Chemical Property:

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Technology Process of D-1-[6-(N,N-dibenzylamino)-6-(benzyloxycarbonyl)]-transhex-2-enoyl-3-amino-1,1,1-trifluorobutan-2-one

There total 6 articles about D-1-[6-(N,N-dibenzylamino)-6-(benzyloxycarbonyl)]-transhex-2-enoyl-3-amino-1,1,1-trifluorobutan-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: 90.0%

D-1-[6-(N,N-dibenzylamino)-6-(benzyloxycarbonyl)]-transhex-2-enoyl-3-amino-1,1,1-trifluoro-2-butanol (1427207-09-7) → D-1-[6-(N,N-dibenzylamino)-6-(benzyloxycarbonyl)]-transhex-2-enoyl-3-amino-1,1,1-trifluorobutan-2-one (1427207-10-0)

Guidance literature:

With Dess-Martin periodane; trifluoroacetic acid; In dichloromethane; at 25 ℃; for 3h;

DOI:10.1021/bi400048s

Reference yield:

D-Glutamic acid (6893-26-1,21675-62-7,23009-64-5,25104-13-6,84960-48-5,25513-46-6) → D-1-[6-(N,N-dibenzylamino)-6-(benzyloxycarbonyl)]-transhex-2-enoyl-3-amino-1,1,1-trifluorobutan-2-one (1427207-10-0)

Guidance literature:

Multi-step reaction with 6 steps

1: sodium hydroxide; potassium carbonate / water / Reflux

2: diisobutylaluminium hydride; water / diethyl ether; hexane / 0.5 h / -78 - 25 °C / Inert atmosphere

3: tetrahydrofuran / 1.5 h / 25 °C

4: trifluoroacetic acid / dichloromethane / 1 h / 25 °C

5: triethylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / N,N-dimethyl-formamide / 24 h / 0 - 25 °C

6: trifluoroacetic acid; Dess-Martin periodane / dichloromethane / 3 h / 25 °C

With water; diisobutylaluminium hydride; potassium carbonate; Dess-Martin periodane; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; trifluoroacetic acid; sodium hydroxide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/bi400048s

Reference yield:

N,N-dibenzyl-D-glutamic acid dibenzyl ester (1237769-99-1) → D-1-[6-(N,N-dibenzylamino)-6-(benzyloxycarbonyl)]-transhex-2-enoyl-3-amino-1,1,1-trifluorobutan-2-one (1427207-10-0)

Guidance literature:

Multi-step reaction with 5 steps

1: diisobutylaluminium hydride; water / diethyl ether; hexane / 0.5 h / -78 - 25 °C / Inert atmosphere

2: tetrahydrofuran / 1.5 h / 25 °C

3: trifluoroacetic acid / dichloromethane / 1 h / 25 °C

4: triethylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / N,N-dimethyl-formamide / 24 h / 0 - 25 °C

5: trifluoroacetic acid; Dess-Martin periodane / dichloromethane / 3 h / 25 °C

With water; diisobutylaluminium hydride; Dess-Martin periodane; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; trifluoroacetic acid; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/bi400048s

upstream raw materials:

D-Glutamic acid

N,N-dibenzyl-D-glutamic acid dibenzyl ester

D-4-(N,N-dibenzylamino)-4-(benzyloxycarbonyl)butanal

D-6-(N,N-dibenzylamino)-6-(benzyloxycarbonyl)-trans-hex-2-enoic acid tert-butyl ester

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