(1R)-2-endo-[(3R,4S)-4-(N-((2S)-benzyloxy-3-methylbutanoyl)-N-methylamino)-3-hydroxy-5-phenylpentanoyl]-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol

Base Information

Chemical Name:(1R)-2-endo-[(3R,4S)-4-(N-((2S)-benzyloxy-3-methylbutanoyl)-N-methylamino)-3-hydroxy-5-phenylpentanoyl]-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol
CAS No.:716371-57-2
Molecular Formula:C₃₄H₄₇NO₅
Molecular Weight:549.751
Hs Code.:

Synonyms:(1R)-2-endo-[(3R,4S)-4-(N-((2S)-benzyloxy-3-methylbutanoyl)-N-methylamino)-3-hydroxy-5-phenylpentanoyl]-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol

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Chemical Property of (1R)-2-endo-[(3R,4S)-4-(N-((2S)-benzyloxy-3-methylbutanoyl)-N-methylamino)-3-hydroxy-5-phenylpentanoyl]-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol

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Technology Process of (1R)-2-endo-[(3R,4S)-4-(N-((2S)-benzyloxy-3-methylbutanoyl)-N-methylamino)-3-hydroxy-5-phenylpentanoyl]-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol

There total 8 articles about (1R)-2-endo-[(3R,4S)-4-(N-((2S)-benzyloxy-3-methylbutanoyl)-N-methylamino)-3-hydroxy-5-phenylpentanoyl]-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol 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: 95.0%

: 716371-56-1
(1R)-2-endo-[(3R,4S)-4-(N-((S)-2-benzyloxy-3-methylbutanoyl)-N-methylamino)-3-hydroxy-5-phenylpentanoyl]-2-exo-trimethylsilyloxy-1,7,7-trimethylbicyclo[2.2.1]heptane

: 716371-57-2
(1R)-2-endo-[(3R,4S)-4-(N-((2S)-benzyloxy-3-methylbutanoyl)-N-methylamino)-3-hydroxy-5-phenylpentanoyl]-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 0.5h;
DOI:10.1021/jo0497499

Reference yield:

: 24164-73-6
methyl (S)-2-(benzyloxycarbonyl-methyl-amino)-3-phenylpropionate

: 716371-57-2
(1R)-2-endo-[(3R,4S)-4-(N-((2S)-benzyloxy-3-methylbutanoyl)-N-methylamino)-3-hydroxy-5-phenylpentanoyl]-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol

Guidance literature:: Multi-step reaction with 5 steps

1.1: DIBAL / hexane; tetrahydrofuran / -78 - -65 °C

2.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -78 °C

2.2: 78 percent / hexane; tetrahydrofuran / 2 h / -78 °C

3.1: 98 percent / H₂ / Pd/C / ethyl acetate / 3 h / 25 °C / balloon

4.1: 80 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 0 - 20 °C

5.1: 95 percent / tetra-n-butyammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C

With dmap; n-butyllithium; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; palladium on activated charcoal; In tetrahydrofuran; hexane; dichloromethane; ethyl acetate;
DOI:10.1021/jo0497499

Reference yield:

: 202134-44-9
(S)-benzyl methyl(1-oxo-3-phenylpropan-2-yl)carbamate

: 716371-57-2
(1R)-2-endo-[(3R,4S)-4-(N-((2S)-benzyloxy-3-methylbutanoyl)-N-methylamino)-3-hydroxy-5-phenylpentanoyl]-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol

Guidance literature:: Multi-step reaction with 4 steps

1.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -78 °C

1.2: 78 percent / hexane; tetrahydrofuran / 2 h / -78 °C

2.1: 98 percent / H₂ / Pd/C / ethyl acetate / 3 h / 25 °C / balloon

3.1: 80 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 0 - 20 °C

4.1: 95 percent / tetra-n-butyammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C

With dmap; n-butyllithium; tetrabutyl ammonium fluoride; hydrogen; palladium on activated charcoal; In tetrahydrofuran; hexane; dichloromethane; ethyl acetate;
DOI:10.1021/jo0497499