(3R,4S)-4-(N-((S)-2-benzyloxy-3-methylbutanoyl)-N-methylamino)-3-tert-butyldimethylsilyloxy-5-phenylpentanoic acid

Base Information

• Chemical Name: (3R,4S)-4-(N-((S)-2-benzyloxy-3-methylbutanoyl)-N-methylamino)-3-tert-butyldimethylsilyloxy-5-phenylpentanoic acid
• CAS No.: 716371-59-4
• Molecular Formula: C₃₀H₄₅NO₅Si
• Molecular Weight: 527.777

Synonyms:(3R,4S)-4-(N-((S)-2-benzyloxy-3-methylbutanoyl)-N-methylamino)-3-tert-butyldimethylsilyloxy-5-phenylpentanoic acid

Chemical Property of (3R,4S)-4-(N-((S)-2-benzyloxy-3-methylbutanoyl)-N-methylamino)-3-tert-butyldimethylsilyloxy-5-phenylpentanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of (3R,4S)-4-(N-((S)-2-benzyloxy-3-methylbutanoyl)-N-methylamino)-3-tert-butyldimethylsilyloxy-5-phenylpentanoic acid

There total 10 articles about (3R,4S)-4-(N-((S)-2-benzyloxy-3-methylbutanoyl)-N-methylamino)-3-tert-butyldimethylsilyloxy-5-phenylpentanoic 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: 86.0%

(1R)-2-endo-[(3R,4S)-4-(N-((2S)-benzyloxy-3-methylbutanoyl)-N-methylamino)-3-tert-butyldimethylsilyloxy-5-phenylpentanoyl]-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol (716371-58-3) → (3R,4S)-4-(N-((S)-2-benzyloxy-3-methylbutanoyl)-N-methylamino)-3-tert-butyldimethylsilyloxy-5-phenylpentanoic acid (716371-59-4)

Guidance literature:

With ammonium cerium(IV) nitrate; In water; acetonitrile; at 0 ℃; for 0.5h;

DOI:10.1021/jo0497499

Reference yield:

methyl (S)-2-(benzyloxycarbonyl-methyl-amino)-3-phenylpropionate (24164-73-6) → (3R,4S)-4-(N-((S)-2-benzyloxy-3-methylbutanoyl)-N-methylamino)-3-tert-butyldimethylsilyloxy-5-phenylpentanoic acid (716371-59-4)

Guidance literature:

Multi-step reaction with 7 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

6.1: 92 percent / pyridine / CH₂Cl₂ / 15 h / 20 °C

7.1: 86 percent / cerium(IV) ammonium nitrate / H₂O; acetonitrile / 0.5 h / 0 °C

With pyridine; dmap; n-butyllithium; ammonium cerium(IV) nitrate; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; palladium on activated charcoal; In tetrahydrofuran; hexane; dichloromethane; water; ethyl acetate; acetonitrile;

DOI:10.1021/jo0497499

Reference yield:

(S)-benzyl methyl(1-oxo-3-phenylpropan-2-yl)carbamate (202134-44-9) → (3R,4S)-4-(N-((S)-2-benzyloxy-3-methylbutanoyl)-N-methylamino)-3-tert-butyldimethylsilyloxy-5-phenylpentanoic acid (716371-59-4)

Guidance literature:

Multi-step reaction with 6 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

5.1: 92 percent / pyridine / CH₂Cl₂ / 15 h / 20 °C

6.1: 86 percent / cerium(IV) ammonium nitrate / H₂O; acetonitrile / 0.5 h / 0 °C

With pyridine; dmap; n-butyllithium; ammonium cerium(IV) nitrate; tetrabutyl ammonium fluoride; hydrogen; palladium on activated charcoal; In tetrahydrofuran; hexane; dichloromethane; water; ethyl acetate; acetonitrile;

DOI:10.1021/jo0497499

upstream raw materials:

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

methyl (S)-2-(benzyloxy)-3-methylbutanoate

(S)-2-(benzyloxy)-3-methylbutanoic acid

methyl (S)-2-(benzyloxycarbonyl-methyl-amino)-3-phenylpropionate

Downstream raw materials:

(-)-hapalosin

(2S,5S,6R,10R,11S)-5-Benzyl-6-(tert-butyl-dimethyl-silanyloxy)-10-heptyl-2-isopropyl-4,11-dimethyl-1,9-dioxa-4-aza-cyclododecane-3,8,12-trione

(2S,3R)-3-((3R,4S)-3-tert-butyldimethylsilyloxy-4-(N-((S)-2-hydroxy-3-methylbutanoyl)-N-methylamino)-5-phenylpentanoyloxy)-2-methyldecanoate

benzyl (2S,3R)-3-((3R,4S)-4-(N-((S)-2-benzyloxy-3-methylbutanoyl)-N-methylamino)-3-tert-butyldimethylsilyloxy-5-phenylpentanoyloxy)-2-methyldecanoate

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