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

Base Information

• Chemical Name: (2S,3R)-3-((3R,4S)-3-tert-butyldimethylsilyloxy-4-(N-((S)-2-hydroxy-3-methylbutanoyl)-N-methylamino)-5-phenylpentanoyloxy)-2-methyldecanoate
• CAS No.: 716371-66-3
• Molecular Formula: C₃₄H₅₉NO₇Si
• Molecular Weight: 621.93
• Mol file: 716371-66-3.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 12 articles about (2S,3R)-3-((3R,4S)-3-tert-butyldimethylsilyloxy-4-(N-((S)-2-hydroxy-3-methylbutanoyl)-N-methylamino)-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:

methyl (S)-2-(benzyloxy)-3-methylbutanoate (110298-78-7) → (2S,3R)-3-((3R,4S)-3-tert-butyldimethylsilyloxy-4-(N-((S)-2-hydroxy-3-methylbutanoyl)-N-methylamino)-5-phenylpentanoyloxy)-2-methyldecanoate (716371-66-3)

Guidance literature:

Multi-step reaction with 9 steps

1: 91 percent / LiOH*H₂O / H₂O; methanol / 3 h / Heating

2: oxalyl chloride / CH₂Cl₂ / 0 - 20 °C

3: 80 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 0 - 20 °C

4: 95 percent / tetra-n-butyammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C

5: 92 percent / pyridine / CH₂Cl₂ / 15 h / 20 °C

6: 86 percent / cerium(IV) ammonium nitrate / H₂O; acetonitrile / 0.5 h / 0 °C

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

8: 80 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 3 h / 20 °C

9: 98 percent / H₂ / Pd/C / ethyl acetate / 1 h / 25 °C / balloon

With pyridine; dmap; lithium hydroxide; oxalyl dichloride; ammonium cerium(IV) nitrate; tetrabutyl ammonium fluoride; hydrogen; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; acetonitrile;

DOI:10.1021/jo0497499

Reference yield:

(S)-2-(benzyloxy)-3-methylbutanoic acid (391871-69-5) → (2S,3R)-3-((3R,4S)-3-tert-butyldimethylsilyloxy-4-(N-((S)-2-hydroxy-3-methylbutanoyl)-N-methylamino)-5-phenylpentanoyloxy)-2-methyldecanoate (716371-66-3)

Guidance literature:

Multi-step reaction with 8 steps

1: oxalyl chloride / CH₂Cl₂ / 0 - 20 °C

2: 80 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 0 - 20 °C

3: 95 percent / tetra-n-butyammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C

4: 92 percent / pyridine / CH₂Cl₂ / 15 h / 20 °C

5: 86 percent / cerium(IV) ammonium nitrate / H₂O; acetonitrile / 0.5 h / 0 °C

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

7: 80 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 3 h / 20 °C

8: 98 percent / H₂ / Pd/C / ethyl acetate / 1 h / 25 °C / balloon

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

DOI:10.1021/jo0497499

Reference yield:

methyl (S)-2-(benzyloxycarbonyl-methyl-amino)-3-phenylpropionate (24164-73-6) → (2S,3R)-3-((3R,4S)-3-tert-butyldimethylsilyloxy-4-(N-((S)-2-hydroxy-3-methylbutanoyl)-N-methylamino)-5-phenylpentanoyloxy)-2-methyldecanoate (716371-66-3)

Guidance literature:

Multi-step reaction with 10 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

10.1: 98 percent / H₂ / Pd/C / ethyl acetate / 1 h / 25 °C / balloon

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

upstream raw materials:

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

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

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

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

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