(2S,3R)-N-methoxy-N-methyl-3-hydroxy-5-(4-methoxybenzyloxy)-2-methylpentamide

Base Information

• Chemical Name: (2S,3R)-N-methoxy-N-methyl-3-hydroxy-5-(4-methoxybenzyloxy)-2-methylpentamide
• CAS No.: 866530-02-1
• Molecular Formula: C₁₆H₂₅NO₅
• Molecular Weight: 311.378
• Mol file: 866530-02-1.mol

Synonyms:(2S,3R)-N-methoxy-N-methyl-3-hydroxy-5-(4-methoxybenzyloxy)-2-methylpentamide

Chemical Property of (2S,3R)-N-methoxy-N-methyl-3-hydroxy-5-(4-methoxybenzyloxy)-2-methylpentamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-N-methoxy-N-methyl-3-hydroxy-5-(4-methoxybenzyloxy)-2-methylpentamide

There total 5 articles about (2S,3R)-N-methoxy-N-methyl-3-hydroxy-5-(4-methoxybenzyloxy)-2-methylpentamide 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:

(3S,4R)-4-[2-(4-methoxybenzyloxy)ethyl]-3-methyloxetan-2-one (900171-30-4) + N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) → (2S,3R)-N-methoxy-N-methyl-3-hydroxy-5-(4-methoxybenzyloxy)-2-methylpentamide (866530-02-1)

Guidance literature:

With dimethylaluminum chloride; In hexane; dichloromethane; at -25 ℃; for 2h;

DOI:10.1021/ja061938g

Reference yield:

N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) + (S)-4-Benzyl-3-[3-hydroxy-5-(4-methoxy-benzyloxy)-2-methyl-pentanoyl]-oxazolidin-2-one → (2S,3R)-N-methoxy-N-methyl-3-hydroxy-5-(4-methoxybenzyloxy)-2-methylpentamide (866530-02-1)

Guidance literature:

With trimethylaluminum; In tetrahydrofuran; at 0 ℃;

DOI:10.1021/ol027211o

Reference yield:

2-(4-methoxy-phenyl)-[1,3]dioxane (5689-71-4) → (2S,3R)-N-methoxy-N-methyl-3-hydroxy-5-(4-methoxybenzyloxy)-2-methylpentamide (866530-02-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: diisobutylaluminum hydride / CH₂Cl₂ / 0 °C

2.1: pyridinium chlorochromate / CH₂Cl₂

3.1: n-Bu₂BOTf; triethylamine / CH₂Cl₂ / -5 °C

3.2: 87 percent / CH₂Cl₂ / -78 °C

4.1: Me₃Al / tetrahydrofuran / 0 °C

With di-n-butylboryl trifluoromethanesulfonate; trimethylaluminum; diisobutylaluminium hydride; triethylamine; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; 3.2: Evans asymmetric aldol condensation;

DOI:10.1021/ol027211o

upstream raw materials:

N,O-dimethylhydroxylamine*hydrochloride

(3S,4R)-4-[2-(4-methoxybenzyloxy)ethyl]-3-methyloxetan-2-one

2-(4-methoxy-phenyl)-[1,3]dioxane

4-methoxy-benzaldehyde

Downstream raw materials:

(2R,3S,4S,5R)-3,5-Dihydroxy-7-(4-methoxy-benzyloxy)-2,4-dimethyl-heptanoic acid

(2S,3R,4S,5R)-5-(tert-butyldimethylsilanyloxy)-3-hydroxy-7-(4-methoxybenzyloxy)-2,4-dimethylheptyl 4-methylbenzenesulfonate

(2S,3R,4S,5R)-5-(tert-butyldimethylsilanyloxy)-3-methoxy-7-(4-methoxybenzyloxy)-2,4-dimethylheptyl 4-methylbenzenesulfonate

(2S,3R,4S,5R)-5-(tert-butyldimethylsilanyloxy)-7-(4-methoxybenzyloxy)-2,4-dimethylheptane-1,3-diol