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

Base Information

• Chemical Name: benzyl (2S,3R)-3-((3R,4S)-4-(N-((S)-2-benzyloxy-3-methylbutanoyl)-N-methylamino)-3-tert-butyldimethylsilyloxy-5-phenylpentanoyloxy)-2-methyldecanoate
• CAS No.: 716371-65-2
• Molecular Formula: C₄₈H₇₁NO₇Si
• Molecular Weight: 802.18
• Mol file: 716371-65-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 11 articles about benzyl (2S,3R)-3-((3R,4S)-4-(N-((S)-2-benzyloxy-3-methylbutanoyl)-N-methylamino)-3-tert-butyldimethylsilyloxy-5-phenylpentanoyloxy)-2-methyldecanoate 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: 80.0%

benzyl (2S,3R)-3-hydroxy-2-methyldecanoate (178113-54-7) + (3R,4S)-4-[((S)-2-Benzyloxy-3-methyl-butyryl)-methyl-amino]-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentanoyl chloride → benzyl (2S,3R)-3-((3R,4S)-4-(N-((S)-2-benzyloxy-3-methylbutanoyl)-N-methylamino)-3-tert-butyldimethylsilyloxy-5-phenylpentanoyloxy)-2-methyldecanoate (716371-65-2)

Guidance literature:

With dmap; In dichloromethane; at 20 ℃; for 3h;

DOI:10.1021/jo0497499

Reference yield:

methyl (S)-2-(benzyloxycarbonyl-methyl-amino)-3-phenylpropionate (24164-73-6) → benzyl (2S,3R)-3-((3R,4S)-4-(N-((S)-2-benzyloxy-3-methylbutanoyl)-N-methylamino)-3-tert-butyldimethylsilyloxy-5-phenylpentanoyloxy)-2-methyldecanoate (716371-65-2)

Guidance literature:

Multi-step reaction with 9 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

8.1: oxalyl chloride / CH₂Cl₂ / 3 h / 0 - 20 °C

9.1: 80 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 3 h / 20 °C

With pyridine; dmap; n-butyllithium; oxalyl dichloride; 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) → benzyl (2S,3R)-3-((3R,4S)-4-(N-((S)-2-benzyloxy-3-methylbutanoyl)-N-methylamino)-3-tert-butyldimethylsilyloxy-5-phenylpentanoyloxy)-2-methyldecanoate (716371-65-2)

Guidance literature:

Multi-step reaction with 8 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

7.1: oxalyl chloride / CH₂Cl₂ / 3 h / 0 - 20 °C

8.1: 80 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 3 h / 20 °C

With pyridine; dmap; n-butyllithium; oxalyl dichloride; 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:

benzyl (2S,3R)-3-hydroxy-2-methyldecanoate

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

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

(2S)-2-(benzyloxy)-3-methylbutanoyl chloride

Downstream raw materials:

(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

(-)-hapalosin