(R)-N-methoxy-2-[(2S,4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxinan-4-yl]-N-methylpropionamide

Base Information

• Chemical Name: (R)-N-methoxy-2-[(2S,4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxinan-4-yl]-N-methylpropionamide
• CAS No.: 303727-84-6
• Molecular Formula: C₁₇H₂₅NO₅
• Molecular Weight: 323.389
• Mol file: 303727-84-6.mol

Synonyms:(R)-N-methoxy-2-[(2S,4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxinan-4-yl]-N-methylpropionamide

Chemical Property of (R)-N-methoxy-2-[(2S,4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxinan-4-yl]-N-methylpropionamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-N-methoxy-2-[(2S,4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxinan-4-yl]-N-methylpropionamide

There total 6 articles about (R)-N-methoxy-2-[(2S,4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxinan-4-yl]-N-methylpropionamide 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: 86.0%

(2R,3S,4S)-3-hydroxy-5-(4-methoxybenzyloxy)-2,4-dimethylpentanoic acid methoxymethylamide (252342-49-7) → (R)-N-methoxy-2-[(2S,4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxinan-4-yl]-N-methylpropionamide (303727-84-6)

Guidance literature:

With 4 A molecular sieve; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; at -10 - 0 ℃;

DOI:10.1021/ja0015287

Reference yield:

(2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2,4-dimethyl-pent-4-enoic acid methoxy-methyl-amide (180628-70-0) → (R)-N-methoxy-2-[(2S,4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxinan-4-yl]-N-methylpropionamide (303727-84-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 83 percent / 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 25 °C

2: tetrabutylammonium fluoride / tetrahydrofuran / 25 °C

3: camphorsulfonic acid

With camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; 9-bora-bicyclo[3.3.1]nonane; In tetrahydrofuran;

DOI:10.1021/ol026968c

Reference yield:

[[3-(2R,3R)-4R]-3-(3-hydroxy-2,4-dimethyl-1-oxopent-4-enyl)-4-(phenylmethyl)]-2-oxazolidinone (186885-60-9) → (R)-N-methoxy-2-[(2S,4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxinan-4-yl]-N-methylpropionamide (303727-84-6)

Guidance literature:

Multi-step reaction with 5 steps

1: Me₃Al / tetrahydrofuran / 0 °C

2: 97 percent / 2,6-lutidine / CH₂Cl₂ / -60 °C

3: 83 percent / 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 25 °C

4: tetrabutylammonium fluoride / tetrahydrofuran / 25 °C

5: camphorsulfonic acid

With 2,6-dimethylpyridine; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; trimethylaluminum; 9-bora-bicyclo[3.3.1]nonane; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ol026968c

upstream raw materials:

(2R,3S,4S)-3-hydroxy-5-(4-methoxybenzyloxy)-2,4-dimethylpentanoic acid methoxymethylamide

(2'R,3'S,4'S,4R,5S)-3-[3'-hydroxy-5'-(4-methoxyphenyl)methoxy-2',4'-dimethylpentanoyl]-5-phenyl-4-methyl-2-oxazolidinone

(2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2,4-dimethyl-pent-4-enoic acid methoxy-methyl-amide

[[3-(2R,3R)-4R]-3-(3-hydroxy-2,4-dimethyl-1-oxopent-4-enyl)-4-(phenylmethyl)]-2-oxazolidinone

Downstream raw materials:

(R)-2-[(4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxinan-4-yl]propionaldehyde

(2R,6R,8S)-9-(benzyloxy)-2-[(4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl]-6,8-dimethylnon-4-yn-3-one

(2S,4S,5S)-4-[(2R,3R,6S,8R,9R,10S,11Z,13S,15S,16S,17E)-3,9,13,15-tetrakis(tert-butyldimethylsilyloxy)-6,8,10,16-tetramethyl-19-(trityloxy)nonadeca-11,17-dien-2-yl]-2-(4-methoxyphenyl)-5-methyl-1,3-dioxane

(2S,3S,6S,8R,9R,10S,11Z,13S,15S,16S,17E)-9,13,15-tris(tert-butyldimethylsilyloxy)-2-[(2S,4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl]-6,8,10,16-tetramethyl-19-(trityloxy)nonadeca-11,17-dien-3-ol