(2S,4S)-6-(tert-butyldiphenylsilanyloxy)-2,4-dimethylhexanoic acid N-[(1R,2R)-2-hydroxy-1-methyl-2-phenylethyl]-N-methylamide

Base Information

• Chemical Name: (2S,4S)-6-(tert-butyldiphenylsilanyloxy)-2,4-dimethylhexanoic acid N-[(1R,2R)-2-hydroxy-1-methyl-2-phenylethyl]-N-methylamide
• CAS No.: 866923-95-7
• Molecular Formula: C₃₄H₄₇NO₃Si
• Molecular Weight: 545.838
• Mol file: 866923-95-7.mol

Synonyms:(2S,4S)-6-(tert-butyldiphenylsilanyloxy)-2,4-dimethylhexanoic acid N-[(1R,2R)-2-hydroxy-1-methyl-2-phenylethyl]-N-methylamide

Chemical Property of (2S,4S)-6-(tert-butyldiphenylsilanyloxy)-2,4-dimethylhexanoic acid N-[(1R,2R)-2-hydroxy-1-methyl-2-phenylethyl]-N-methylamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4S)-6-(tert-butyldiphenylsilanyloxy)-2,4-dimethylhexanoic acid N-[(1R,2R)-2-hydroxy-1-methyl-2-phenylethyl]-N-methylamide

There total 1 articles about (2S,4S)-6-(tert-butyldiphenylsilanyloxy)-2,4-dimethylhexanoic acid N-[(1R,2R)-2-hydroxy-1-methyl-2-phenylethyl]-N-methylamide 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: 76.0%

(1R,2R)-(-)-pseudoephedrinepropionamide (192060-67-6) + (3R)-4-iodo-3-methyl-1-butyl tert-butyldiphenylsilyl ether (275804-95-0) → (2S,4S)-6-(tert-butyldiphenylsilanyloxy)-2,4-dimethylhexanoic acid N-[(1R,2R)-2-hydroxy-1-methyl-2-phenylethyl]-N-methylamide (866923-95-7)

Guidance literature:

With n-butyllithium; diisopropylamine; lithium chloride; In tetrahydrofuran; hexane; at 0 - 23 ℃;

DOI:10.1021/ol051785m

Reference yield: 90.0%

(2S,4S)-6-(tert-butyldiphenylsilanyloxy)-2,4-dimethylhexanoic acid N-[(1R,2R)-2-hydroxy-1-methyl-2-phenylethyl]-N-methylamide (866923-95-7) → (2S,4S)-6-(tert-butyldiphenylsilanyloxy)-2,4-dimethylhexan-1-ol (866923-96-8)

Guidance literature:

With n-butyllithium; borane-ammonia complex; diisopropylamine; In tetrahydrofuran; hexane; at 0 - 23 ℃;

DOI:10.1021/ol051785m

Reference yield:

(2S,4S)-6-(tert-butyldiphenylsilanyloxy)-2,4-dimethylhexanoic acid N-[(1R,2R)-2-hydroxy-1-methyl-2-phenylethyl]-N-methylamide (866923-95-7) → (2S,4S)-6-(tert-butyldiphenylsilanyloxy)-2,4-dimethylhexanal (866923-88-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / n-BuLi; BH₃*NH₃; N,N-diisopropylamine / tetrahydrofuran; hexane / 0 - 23 °C

2: 80 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 0.5 h / 23 °C

With n-butyllithium; borane-ammonia complex; sodium hydrogencarbonate; Dess-Martin periodane; diisopropylamine; In tetrahydrofuran; hexane; dichloromethane; 2: Dess-Martin oxidation;

DOI:10.1021/ol051785m

upstream raw materials:

(1R,2R)-(-)-pseudoephedrinepropionamide

(3R)-4-iodo-3-methyl-1-butyl tert-butyldiphenylsilyl ether

Downstream raw materials:

(2S,4S)-6-(tert-butyldiphenylsilanyloxy)-2,4-dimethylhexan-1-ol

(2S,4S)-6-(tert-butyldiphenylsilanyloxy)-2,4-dimethylhexanal