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

Base Information

Chemical Name:(1R)-2-endo-[(3R,4S)-3-hydroxy-4-(N-methylamino)-5-phenylpentanoyl]-2-exo-trimethylsilyloxy-1,7,7-trimethylbicyclo[2.2.1]heptane
CAS No.:716371-55-0
Molecular Formula:C₂₅H₄₁NO₃Si
Molecular Weight:431.691
Hs Code.:

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

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Chemical Property of (1R)-2-endo-[(3R,4S)-3-hydroxy-4-(N-methylamino)-5-phenylpentanoyl]-2-exo-trimethylsilyloxy-1,7,7-trimethylbicyclo[2.2.1]heptane

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Technology Process of (1R)-2-endo-[(3R,4S)-3-hydroxy-4-(N-methylamino)-5-phenylpentanoyl]-2-exo-trimethylsilyloxy-1,7,7-trimethylbicyclo[2.2.1]heptane

There total 3 articles about (1R)-2-endo-[(3R,4S)-3-hydroxy-4-(N-methylamino)-5-phenylpentanoyl]-2-exo-trimethylsilyloxy-1,7,7-trimethylbicyclo[2.2.1]heptane 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: 98.0%

: 716371-47-0
(1R)-2-endo-[(3R,4S)-4-(N-benzyloxycarbonyl-N-methylamino)-3-hydroxy-5-phenylpentanoyl]-2-exo-trimethylsilyloxy-1,7,7-trimethylbicyclo[2.2.1]heptane

: 716371-55-0
(1R)-2-endo-[(3R,4S)-3-hydroxy-4-(N-methylamino)-5-phenylpentanoyl]-2-exo-trimethylsilyloxy-1,7,7-trimethylbicyclo[2.2.1]heptane

Guidance literature:: With hydrogen; palladium on activated charcoal; In ethyl acetate; at 25 ℃; for 3h; balloon;
DOI:10.1021/jo0497499

Reference yield:

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

: 716371-55-0
(1R)-2-endo-[(3R,4S)-3-hydroxy-4-(N-methylamino)-5-phenylpentanoyl]-2-exo-trimethylsilyloxy-1,7,7-trimethylbicyclo[2.2.1]heptane

Guidance literature:: Multi-step reaction with 3 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

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

Reference yield:

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

: 716371-55-0
(1R)-2-endo-[(3R,4S)-3-hydroxy-4-(N-methylamino)-5-phenylpentanoyl]-2-exo-trimethylsilyloxy-1,7,7-trimethylbicyclo[2.2.1]heptane

Guidance literature:: Multi-step reaction with 2 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

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