(2R,3R)-2-(tert-butoxycarbonylamino)-3-[(S)-1-(methylamino)-1-oxo-3-phenylpropan-2-ylcarbamoyl]-6-phenylhexanoic acid

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Chemical Name:(2R,3R)-2-(tert-butoxycarbonylamino)-3-[(S)-1-(methylamino)-1-oxo-3-phenylpropan-2-ylcarbamoyl]-6-phenylhexanoic acid
CAS No.:1374429-26-1
Molecular Formula:C₂₈H₃₇N₃O₆
Molecular Weight:511.618
Hs Code.:

Synonyms:(2R,3R)-2-(tert-butoxycarbonylamino)-3-[(S)-1-(methylamino)-1-oxo-3-phenylpropan-2-ylcarbamoyl]-6-phenylhexanoic acid

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Chemical Property of (2R,3R)-2-(tert-butoxycarbonylamino)-3-[(S)-1-(methylamino)-1-oxo-3-phenylpropan-2-ylcarbamoyl]-6-phenylhexanoic acid

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Technology Process of (2R,3R)-2-(tert-butoxycarbonylamino)-3-[(S)-1-(methylamino)-1-oxo-3-phenylpropan-2-ylcarbamoyl]-6-phenylhexanoic acid

There total 11 articles about (2R,3R)-2-(tert-butoxycarbonylamino)-3-[(S)-1-(methylamino)-1-oxo-3-phenylpropan-2-ylcarbamoyl]-6-phenylhexanoic acid 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%

: 1374429-36-3
N-methyl-(R)-2-[(R)-2-(benzyloxy)-1-(tert-butoxycarbonylamino)-2-oxoethyl]-5-phenylpentanoyl-(S)-phenylalanineamide

: 1374429-26-1
(2R,3R)-2-(tert-butoxycarbonylamino)-3-[(S)-1-(methylamino)-1-oxo-3-phenylpropan-2-ylcarbamoyl]-6-phenylhexanoic acid

Guidance literature:: With palladium 10% on activated carbon; hydrogen; In tetrahydrofuran; at 20 ℃; for 3h; Inert atmosphere;
DOI:10.1002/ejoc.201101318

Reference yield:

: (E)-7-phenylhept-3-en-2-ol

: 1374429-26-1
(2R,3R)-2-(tert-butoxycarbonylamino)-3-[(S)-1-(methylamino)-1-oxo-3-phenylpropan-2-ylcarbamoyl]-6-phenylhexanoic acid

Guidance literature:: Multi-step reaction with 9 steps

1.1: Novozym 435 / 18 h / 20 °C / Inert atmosphere; Enzymatic reaction

2.1: water; sodium hydroxide / methanol / 0 - 20 °C / Inert atmosphere

3.1: dmap; dicyclohexyl-carbodiimide / diethyl ether / 20 h / 0 - 20 °C / Inert atmosphere

4.1: n-butyllithium; diisopropylamine; zinc(II) chloride / tetrahydrofuran; hexane / -78 - 20 °C / Inert atmosphere

5.1: caesium carbonate / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere

6.1: ozone / dichloromethane / 0.08 h / -78 °C / Inert atmosphere

6.2: 0.5 h / -78 - 20 °C / Inert atmosphere

7.1: sodium chlorite; sodium dihydrogen phosphate monohydrate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 16 h / 20 °C / Inert atmosphere

8.1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine / dichloromethane / 18 h / 0 - 20 °C / Inert atmosphere

9.1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere

With dmap; sodium chlorite; n-butyllithium; sodium dihydrogen phosphate monohydrate; 2-methyl-but-2-ene; Novozym 435; palladium 10% on activated carbon; water; hydrogen; caesium carbonate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; ozone; triethylamine; diisopropylamine; dicyclohexyl-carbodiimide; sodium hydroxide; zinc(II) chloride; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 4.1: Claisen rearrangement;
DOI:10.1002/ejoc.201101318

Reference yield:

: 4530-20-5
BOC-glycine

: 1374429-26-1
(2R,3R)-2-(tert-butoxycarbonylamino)-3-[(S)-1-(methylamino)-1-oxo-3-phenylpropan-2-ylcarbamoyl]-6-phenylhexanoic acid

Guidance literature:: Multi-step reaction with 7 steps

1.1: dmap; dicyclohexyl-carbodiimide / diethyl ether / 20 h / 0 - 20 °C / Inert atmosphere

2.1: n-butyllithium; diisopropylamine; zinc(II) chloride / tetrahydrofuran; hexane / -78 - 20 °C / Inert atmosphere

3.1: caesium carbonate / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere

4.1: ozone / dichloromethane / 0.08 h / -78 °C / Inert atmosphere

4.2: 0.5 h / -78 - 20 °C / Inert atmosphere

5.1: sodium chlorite; sodium dihydrogen phosphate monohydrate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 16 h / 20 °C / Inert atmosphere

6.1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine / dichloromethane / 18 h / 0 - 20 °C / Inert atmosphere

7.1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere

With dmap; sodium chlorite; n-butyllithium; sodium dihydrogen phosphate monohydrate; 2-methyl-but-2-ene; palladium 10% on activated carbon; hydrogen; caesium carbonate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; ozone; triethylamine; diisopropylamine; dicyclohexyl-carbodiimide; zinc(II) chloride; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 2.1: Claisen rearrangement;
DOI:10.1002/ejoc.201101318