(2R,3S)-5-Benzyloxy-3-methoxy-2-methyl-pentanoic acid methoxy-methyl-amide

Base Information

• Chemical Name: (2R,3S)-5-Benzyloxy-3-methoxy-2-methyl-pentanoic acid methoxy-methyl-amide
• CAS No.: 245039-84-3
• Molecular Formula: C₁₆H₂₅NO₄
• Molecular Weight: 295.379
• Mol file: 245039-84-3.mol

Synonyms:(2R,3S)-5-Benzyloxy-3-methoxy-2-methyl-pentanoic acid methoxy-methyl-amide

Chemical Property of (2R,3S)-5-Benzyloxy-3-methoxy-2-methyl-pentanoic acid methoxy-methyl-amide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S)-5-Benzyloxy-3-methoxy-2-methyl-pentanoic acid methoxy-methyl-amide

There total 1 articles about (2R,3S)-5-Benzyloxy-3-methoxy-2-methyl-pentanoic 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: 92.0%

(2R,3S)-5-(benzyloxy)-3-hydroxy-N-methoxy-N,2-dimethylpentanamide (179945-11-0) + methyl iodide (74-88-4) → (2R,3S)-5-Benzyloxy-3-methoxy-2-methyl-pentanoic acid methoxy-methyl-amide (245039-84-3)

Guidance literature:

With sodium hydride;

DOI:10.1016/S0040-4039(99)00868-0

Reference yield: 92.0%

methylmagnesium bromide (75-16-1) + (2R,3S)-5-Benzyloxy-3-methoxy-2-methyl-pentanoic acid methoxy-methyl-amide (245039-84-3) → (3R,4S)-6-Benzyloxy-4-methoxy-3-methyl-hexan-2-one (245039-82-1)

Guidance literature:

In tetrahydrofuran; at 0 ℃;

DOI:10.1016/S0040-4039(99)00868-0

Reference yield:

(2R,3S)-5-Benzyloxy-3-methoxy-2-methyl-pentanoic acid methoxy-methyl-amide (245039-84-3) → (E)-6-Benzyloxy-1-{(4R,5S,6S)-6-[(1R,2S,3S)-2-(tert-butyl-dimethyl-silanyloxy)-4-(tert-butyl-diphenyl-silanyloxy)-1,3-dimethyl-butyl]-5-methyl-[1,3]dioxan-4-yl}-3-methyl-hex-3-en-2-one

Guidance literature:

Multi-step reaction with 3 steps

1: 92 percent / tetrahydrofuran / 0 °C

2: LHMDS / tetrahydrofuran / -78 °C

3: 50 percent / Me₂BBrz; DTBMP / CH₂Cl₂ / -78 °C

With 2,6-di-tert-butyl-4-methylpyridine; Me₂BBrz; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; 1: Grignard reaction / 2: Addition / 3: Etherification;

DOI:10.1016/S0040-4039(99)00868-0

upstream raw materials:

(2R,3S)-5-(benzyloxy)-3-hydroxy-N-methoxy-N,2-dimethylpentanamide

methyl iodide

Downstream raw materials:

(3R,4S)-6-Benzyloxy-4-methoxy-3-methyl-hexan-2-one

(3S,4R,7R,8S,9S,10R,11S,12S)-1-[(benzyl)oxy]-11-[(tert-butyl-dimethylsilyl)oxy]-13-[(tert-butyl-diphenylsilyl)oxy]-7-hydroxy-3-methoxy-9-[(methoxymethyl)oxy]-4,8,10,12-tetramethyl-tridecan-5-one