(2R,3R,4S,7S)-7-(3-Benzyloxy-phenyl)-3-hydroxy-7-methoxy-2,4-dimethyl-heptanoic acid methoxy-methyl-amide

Base Information

• Chemical Name: (2R,3R,4S,7S)-7-(3-Benzyloxy-phenyl)-3-hydroxy-7-methoxy-2,4-dimethyl-heptanoic acid methoxy-methyl-amide
• CAS No.: 909119-59-1
• Molecular Formula: C₂₅H₃₅NO₅
• Molecular Weight: 429.557
• Mol file: 909119-59-1.mol

Synonyms:(2R,3R,4S,7S)-7-(3-Benzyloxy-phenyl)-3-hydroxy-7-methoxy-2,4-dimethyl-heptanoic acid methoxy-methyl-amide

Chemical Property of (2R,3R,4S,7S)-7-(3-Benzyloxy-phenyl)-3-hydroxy-7-methoxy-2,4-dimethyl-heptanoic acid methoxy-methyl-amide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4S,7S)-7-(3-Benzyloxy-phenyl)-3-hydroxy-7-methoxy-2,4-dimethyl-heptanoic acid methoxy-methyl-amide

There total 13 articles about (2R,3R,4S,7S)-7-(3-Benzyloxy-phenyl)-3-hydroxy-7-methoxy-2,4-dimethyl-heptanoic acid methoxy-methyl-amide 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:

(2R,3R,4S,7S)-3-Benzyloxy-7-(3-benzyloxy-phenyl)-7-methoxy-2,4-dimethyl-heptanoic acid methoxy-methyl-amide (909119-53-5) → (2R,3R,4S,7S)-7-(3-Benzyloxy-phenyl)-3-hydroxy-7-methoxy-2,4-dimethyl-heptanoic acid methoxy-methyl-amide (909119-59-1)

Guidance literature:

With hydrogen; palladium on activated charcoal; In toluene; at 20 ℃; for 3h; under 760 Torr;

DOI:10.1016/j.tetlet.2006.05.109

Reference yield:

(S)-3-(3-Benzyloxy-phenyl)-1-((S)-4-isopropyl-2-thioxo-thiazolidin-3-yl)-3-methoxy-propan-1-one (909391-19-1) → (2R,3R,4S,7S)-7-(3-Benzyloxy-phenyl)-3-hydroxy-7-methoxy-2,4-dimethyl-heptanoic acid methoxy-methyl-amide (909119-59-1)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 87 percent / NaBH₄ / tetrahydrofuran / 4 h / 20 °C

2.1: 97 percent / I₂; Ph₃P; imidazole / CH₂Cl₂ / 1.5 h / 20 °C

3.1: 100 percent / LDA / tetrahydrofuran; various solvent(s) / 2 h / -78 °C

4.1: 91 percent / TMSOTf; 2,6-lutidine / CH₂Cl₂ / 2 h / 0 °C

5.1: t-BuOCOCl; Et₃N / tetrahydrofuran / 2 h / 0 °C

5.2: 93 percent / BuLi / tetrahydrofuran / 0.5 h / -78 °C

6.1: NaHMDS / tetrahydrofuran / 2 h / -78 °C

6.2: 78 percent / tetrahydrofuran / 3 h / -78 °C

7.1: 91 percent / LiBH₄ / methanol; tetrahydrofuran / 17 h / -20 °C

8.1: 96 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

9.1: 78 percent / TMSOTf / CH₂Cl₂ / -50 °C

10.1: TiCln

10.2: 74 percent / SnCl₄ / CH₂Cl₂ / 2 h / -20 °C

11.1: 90 percent / Et₃N / DMAP / CH₂Cl₂ / 16 h / 20 °C

12.1: H₂ / Pd/C / toluene / 3 h / 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; sodium tetrahydroborate; lithium borohydride; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; hydrogen; iodine; sodium hexamethyldisilazane; dimethyl sulfoxide; tert-butyl chloroformate; triethylamine; triphenylphosphine; lithium diisopropyl amide; dmap; palladium on activated charcoal; trimethylsilyl trifluoromethanesulfonate; In tetrahydrofuran; methanol; dichloromethane; toluene; 8.1: Swern oxidation;

DOI:10.1016/j.tetlet.2006.05.187

Reference yield:

1-Benzyloxy-3-((S)-3-iodo-1-methoxy-propyl)-benzene (909391-20-4) → (2R,3R,4S,7S)-7-(3-Benzyloxy-phenyl)-3-hydroxy-7-methoxy-2,4-dimethyl-heptanoic acid methoxy-methyl-amide (909119-59-1)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 100 percent / LDA / tetrahydrofuran; various solvent(s) / 2 h / -78 °C

2.1: 91 percent / TMSOTf; 2,6-lutidine / CH₂Cl₂ / 2 h / 0 °C

3.1: t-BuOCOCl; Et₃N / tetrahydrofuran / 2 h / 0 °C

3.2: 93 percent / BuLi / tetrahydrofuran / 0.5 h / -78 °C

4.1: NaHMDS / tetrahydrofuran / 2 h / -78 °C

4.2: 78 percent / tetrahydrofuran / 3 h / -78 °C

5.1: 91 percent / LiBH₄ / methanol; tetrahydrofuran / 17 h / -20 °C

6.1: 96 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

7.1: 78 percent / TMSOTf / CH₂Cl₂ / -50 °C

8.1: TiCln

8.2: 74 percent / SnCl₄ / CH₂Cl₂ / 2 h / -20 °C

9.1: 90 percent / Et₃N / DMAP / CH₂Cl₂ / 16 h / 20 °C

10.1: H₂ / Pd/C / toluene / 3 h / 20 °C

With 2,6-dimethylpyridine; lithium borohydride; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; hydrogen; sodium hexamethyldisilazane; dimethyl sulfoxide; tert-butyl chloroformate; triethylamine; lithium diisopropyl amide; dmap; palladium on activated charcoal; trimethylsilyl trifluoromethanesulfonate; In tetrahydrofuran; methanol; dichloromethane; toluene; 6.1: Swern oxidation;

DOI:10.1016/j.tetlet.2006.05.187

upstream raw materials:

(2R,3R,4S,7S)-3-Benzyloxy-7-(3-benzyloxy-phenyl)-7-methoxy-2,4-dimethyl-heptanoic acid methoxy-methyl-amide

1-Benzyloxy-3-((S)-3-iodo-1-methoxy-propyl)-benzene

(2S,5S)-5-(3-Benzyloxy-phenyl)-5-methoxy-2-methyl-pentanal

(2S,5S)-5-(3-Benzyloxy-phenyl)-5-methoxy-2-methyl-pentan-1-ol

Downstream raw materials:

(Z)-(4S,5R,6S,9S)-5-(tert-Butyl-dimethyl-silanyloxy)-9-[3-(tert-butyl-dimethyl-silanyloxy)-phenyl]-9-methoxy-4,6-dimethyl-non-2-enoic acid methyl ester

3-(tert-butyl-dimethyl-silanyloxy)-7-[3-(tert-butyl-dimethyl-silanyloxy)-phenyl]-7-methoxy-2,4-dimethyl-heptanoic acid methoxy-methyl-amide

3-(tert-butyl-dimethyl-silanyloxy)-7-[3-(tert-butyl-dimethyl-silanyloxy)-phenyl]-7-methoxy-2,4-dimethyl-heptanal

(2R,3R,4S,7S)-3-Hydroxy-7-(3-hydroxy-phenyl)-7-methoxy-2,4-dimethyl-heptanoic acid methoxy-methyl-amide