(1R,2S)-2-((N-benzyl-2,4,6-trimethylphenyl)sulfonamido)-1-phenylpropyl(2R,3S,4S)-4-(dibenzylamino)-3-hydroxy-2-methyl-5-(pyridin-3-yl)pentanoate

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Chemical Name:(1R,2S)-2-((N-benzyl-2,4,6-trimethylphenyl)sulfonamido)-1-phenylpropyl(2R,3S,4S)-4-(dibenzylamino)-3-hydroxy-2-methyl-5-(pyridin-3-yl)pentanoate
CAS No.:1416772-51-4
Molecular Formula:C₅₀H₅₅N₃O₅S
Molecular Weight:810.07
Hs Code.:

Synonyms:(1R,2S)-2-((N-benzyl-2,4,6-trimethylphenyl)sulfonamido)-1-phenylpropyl(2R,3S,4S)-4-(dibenzylamino)-3-hydroxy-2-methyl-5-(pyridin-3-yl)pentanoate

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Chemical Property of (1R,2S)-2-((N-benzyl-2,4,6-trimethylphenyl)sulfonamido)-1-phenylpropyl(2R,3S,4S)-4-(dibenzylamino)-3-hydroxy-2-methyl-5-(pyridin-3-yl)pentanoate

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Technology Process of (1R,2S)-2-((N-benzyl-2,4,6-trimethylphenyl)sulfonamido)-1-phenylpropyl(2R,3S,4S)-4-(dibenzylamino)-3-hydroxy-2-methyl-5-(pyridin-3-yl)pentanoate

There total 10 articles about (1R,2S)-2-((N-benzyl-2,4,6-trimethylphenyl)sulfonamido)-1-phenylpropyl(2R,3S,4S)-4-(dibenzylamino)-3-hydroxy-2-methyl-5-(pyridin-3-yl)pentanoate 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: 45.0%

: 1416772-48-9
C₂₂H₂₂N₂O

: 187324-66-9
(1R,2S)-2-(N-benzyl-N-mesitylenesulfonyl)amino-1-phenyl-1-propyl propionate

: 1416772-51-4
(1R,2S)-2-((N-benzyl-2,4,6-trimethylphenyl)sulfonamido)-1-phenylpropyl(2R,3S,4S)-4-(dibenzylamino)-3-hydroxy-2-methyl-5-(pyridin-3-yl)pentanoate

: (1R,2S)-2-((N-benzyl-2,4,6-trimethylphenyl)sulfonamido)-1-phenylpropyl(2S,3R,4S)-4-(dibenzylamino)-3-hydroxy-2-methyl-5-(pyridin-3-yl)pentanoate

Guidance literature:: (1R,2S)-2-(N-benzyl-N-mesitylenesulfonyl)amino-1-phenyl-1-propyl propionate; With triethylamine; dicyclohexyl(((trifluoromethyl)sulfonyl)oxy)borane; In hexane; dichloromethane; at -78 ℃; for 3.25h; Inert atmosphere; Schlenk technique;

C₂₂H₂₂N₂O; In hexane; dichloromethane; at -78 - 0 ℃; Inert atmosphere; Schlenk technique;
DOI:10.1021/acs.jmedchem.9b01457

Reference yield:

: 1416772-48-9
C₂₂H₂₂N₂O

: 187324-66-9
(1R,2S)-2-(N-benzyl-N-mesitylenesulfonyl)amino-1-phenyl-1-propyl propionate

: C₅₀H₅₅N₃O₅S

: 1416772-51-4
(1R,2S)-2-((N-benzyl-2,4,6-trimethylphenyl)sulfonamido)-1-phenylpropyl(2R,3S,4S)-4-(dibenzylamino)-3-hydroxy-2-methyl-5-(pyridin-3-yl)pentanoate

Guidance literature:: (1R,2S)-2-(N-benzyl-N-mesitylenesulfonyl)amino-1-phenyl-1-propyl propionate; With triethylamine; dicyclohexyl(((trifluoromethyl)sulfonyl)oxy)borane; In hexane; dichloromethane; at -78 ℃; for 3h; Inert atmosphere; Schlenk technique;

C₂₂H₂₂N₂O; In dichloromethane; at -78 - 0 ℃; for 4.3h; Overall yield = 73 %; Overall yield = 71.1 mg;
DOI:10.1021/ml300385q

Reference yield:

: 89890-92-6
N-acetyl-(β-3-pyridyl)-α,β-dehydroalanine

: 1416772-51-4
(1R,2S)-2-((N-benzyl-2,4,6-trimethylphenyl)sulfonamido)-1-phenylpropyl(2R,3S,4S)-4-(dibenzylamino)-3-hydroxy-2-methyl-5-(pyridin-3-yl)pentanoate

Guidance literature:: Multi-step reaction with 7 steps

1.1: sodium acetate / 72 h / 20 °C / Inert atmosphere; Schlenk technique

2.1: tetrafluoroboric acid; (R,R)-(-)-1,2-bis[(o-methoxyphenyl)(phenyl) phosphino]ethane(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; hydrogen / methanol / 18 h / 50 °C / 3750.38 Torr / Autoclave; Schlenk technique

3.1: thionyl chloride / methanol / 18 h / 0 - 80 °C / Inert atmosphere; Schlenk technique

4.1: sodium cyanoborohydride; acetic acid / methanol / 24 h / 20 °C / Molecular sieve; Inert atmosphere; Schlenk technique

5.1: lithium aluminium tetrahydride / diethyl ether / 0.5 h / 0 °C / Inert atmosphere; Schlenk technique

6.1: Dess-Martin periodane / dichloromethane / 0.5 h / 0 °C / Inert atmosphere; Schlenk technique

7.1: triethylamine; dicyclohexyl(((trifluoromethyl)sulfonyl)oxy)borane / dichloromethane; hexane / 3 h / -78 °C / Inert atmosphere; Schlenk technique

7.2: 4.3 h / -78 - 0 °C

With lithium aluminium tetrahydride; tetrafluoroboric acid; thionyl chloride; (R,R)-(-)-1,2-bis[(o-methoxyphenyl)(phenyl) phosphino]ethane(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; hydrogen; sodium acetate; sodium cyanoborohydride; Dess-Martin periodane; acetic acid; triethylamine; dicyclohexyl(((trifluoromethyl)sulfonyl)oxy)borane; In methanol; diethyl ether; hexane; dichloromethane;
DOI:10.1021/ml300385q