dimethyl (3R,4R,6R,7R,8S)-2-[4-[3-(cyclopentyloxy)-4-(methyloxy)phenyl-6-[(2-phenylcyclohexyl)oxy]-1,2-oxazinan-3-yl]methyl]propanedioate

Base Information

• Chemical Name: dimethyl (3R,4R,6R,7R,8S)-2-[4-[3-(cyclopentyloxy)-4-(methyloxy)phenyl-6-[(2-phenylcyclohexyl)oxy]-1,2-oxazinan-3-yl]methyl]propanedioate
• CAS No.: 1335214-55-5
• Molecular Formula: C₃₄H₄₅NO₈
• Molecular Weight: 595.733
• Mol file: 1335214-55-5.mol

Synonyms:dimethyl (3R,4R,6R,7R,8S)-2-[4-[3-(cyclopentyloxy)-4-(methyloxy)phenyl-6-[(2-phenylcyclohexyl)oxy]-1,2-oxazinan-3-yl]methyl]propanedioate

Chemical Property of dimethyl (3R,4R,6R,7R,8S)-2-[4-[3-(cyclopentyloxy)-4-(methyloxy)phenyl-6-[(2-phenylcyclohexyl)oxy]-1,2-oxazinan-3-yl]methyl]propanedioate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of dimethyl (3R,4R,6R,7R,8S)-2-[4-[3-(cyclopentyloxy)-4-(methyloxy)phenyl-6-[(2-phenylcyclohexyl)oxy]-1,2-oxazinan-3-yl]methyl]propanedioate

There total 7 articles about dimethyl (3R,4R,6R,7R,8S)-2-[4-[3-(cyclopentyloxy)-4-(methyloxy)phenyl-6-[(2-phenylcyclohexyl)oxy]-1,2-oxazinan-3-yl]methyl]propanedioate 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: 95.0%

dimethyl (4R,6R,7S,8S)-2-[4-[3-(cyclopentyloxy)-4-(methyloxy)phenyl-6-[(2-phenylcyclohexyl)oxy]-5,6-dihydro-4H-1,2-oxazin-3-yl]methyl]propanedioate (1335214-50-0) → dimethyl (3R,4R,6R,7R,8S)-2-[4-[3-(cyclopentyloxy)-4-(methyloxy)phenyl-6-[(2-phenylcyclohexyl)oxy]-1,2-oxazinan-3-yl]methyl]propanedioate (1335214-55-5)

Guidance literature:

With sodium cyanoborohydride; acetic acid; at 20 ℃; for 1.5h; stereoselective reaction; Inert atmosphere;

DOI:10.1021/jo201331h

Reference yield:

C15H19NO4 (193749-08-5) → dimethyl (3R,4R,6R,7R,8S)-2-[4-[3-(cyclopentyloxy)-4-(methyloxy)phenyl-6-[(2-phenylcyclohexyl)oxy]-1,2-oxazinan-3-yl]methyl]propanedioate (1335214-55-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: tin(IV) chloride / dichloromethane / 0.17 h / -90 °C / Inert atmosphere

2.1: trimethylsilyl bromide; triethylamine / acetonitrile / 48 h / -30 °C / Inert atmosphere

3.1: sodium hydride / tetrahydrofuran; mineral oil / 0.08 h / 0 °C / Inert atmosphere

3.2: 2 h / 50 - 60 °C

4.1: sodium cyanoborohydride; acetic acid / 1.5 h / 20 °C / Inert atmosphere

With trimethylsilyl bromide; tin(IV) chloride; sodium hydride; sodium cyanoborohydride; acetic acid; triethylamine; In tetrahydrofuran; dichloromethane; acetonitrile; mineral oil;

DOI:10.1021/jo201331h

Reference yield:

(4R,6R,7R,8S)-4-[3-(cyclopentyloxy)-4-(methyloxy)phenyl]-3-methyl-6-[(2-phenylcyclohexyl)oxy]-5,6-dihydro-4H-1,2-oxazine 2-oxide (1335214-43-1) → dimethyl (3R,4R,6R,7R,8S)-2-[4-[3-(cyclopentyloxy)-4-(methyloxy)phenyl-6-[(2-phenylcyclohexyl)oxy]-1,2-oxazinan-3-yl]methyl]propanedioate (1335214-55-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: trimethylsilyl bromide; triethylamine / acetonitrile / 48 h / -30 °C / Inert atmosphere

2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.08 h / 0 °C / Inert atmosphere

2.2: 2 h / 50 - 60 °C

3.1: sodium cyanoborohydride; acetic acid / 1.5 h / 20 °C / Inert atmosphere

With trimethylsilyl bromide; sodium hydride; sodium cyanoborohydride; acetic acid; triethylamine; In tetrahydrofuran; acetonitrile; mineral oil;

DOI:10.1021/jo201331h

upstream raw materials:

C₁₅H₁₉NO₄

(4R,6R,7R,8S)-4-[3-(cyclopentyloxy)-4-(methyloxy)phenyl]-3-methyl-6-[(2-phenylcyclohexyl)oxy]-5,6-dihydro-4H-1,2-oxazine 2-oxide

(4R,6R,7R,8S)-3-(bromomethyl)-4-[3-(cyclopentyloxy)-4-(methyloxy)phenyl]-6-[(2-phenylcyclohexyl)oxy]-5,6-dihydro-4H-1,2-oxazine

malonic acid dimethyl ester

Downstream raw materials:

(7R,7aR)-7-[3-(cyclopentyloxy)-4-(methyloxy)phenyl]hexahydro-3H-pyrrolizin-3-one