(2R,5S,6R,1'E,2''RS)-5,6-dihydro-6-(2'-ethoxycarbonyleth-1'-enyl)-2-(p-methoxyphenoxy)-5-(tetrahydro-2''H-pyran-2''-yloxy)-2H-pyran

Base Information

• Chemical Name: (2R,5S,6R,1'E,2''RS)-5,6-dihydro-6-(2'-ethoxycarbonyleth-1'-enyl)-2-(p-methoxyphenoxy)-5-(tetrahydro-2''H-pyran-2''-yloxy)-2H-pyran
• CAS No.: 389860-55-3
• Molecular Formula: C₂₂H₂₈O₇
• Molecular Weight: 404.46
• Mol file: 389860-55-3.mol

Synonyms:(2R,5S,6R,1'E,2''RS)-5,6-dihydro-6-(2'-ethoxycarbonyleth-1'-enyl)-2-(p-methoxyphenoxy)-5-(tetrahydro-2''H-pyran-2''-yloxy)-2H-pyran

Chemical Property of (2R,5S,6R,1'E,2''RS)-5,6-dihydro-6-(2'-ethoxycarbonyleth-1'-enyl)-2-(p-methoxyphenoxy)-5-(tetrahydro-2''H-pyran-2''-yloxy)-2H-pyran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,5S,6R,1'E,2''RS)-5,6-dihydro-6-(2'-ethoxycarbonyleth-1'-enyl)-2-(p-methoxyphenoxy)-5-(tetrahydro-2''H-pyran-2''-yloxy)-2H-pyran

There total 2 articles about (2R,5S,6R,1'E,2''RS)-5,6-dihydro-6-(2'-ethoxycarbonyleth-1'-enyl)-2-(p-methoxyphenoxy)-5-(tetrahydro-2''H-pyran-2''-yloxy)-2H-pyran 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:

diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) + (2S,3S,6R)-6-(4-Methoxy-phenoxy)-3-(tetrahydro-pyran-2-yloxy)-3,6-dihydro-2H-pyran-2-carbaldehyde → (2R,5S,6R,1'E,2''RS)-5,6-dihydro-6-(2'-ethoxycarbonyleth-1'-enyl)-2-(p-methoxyphenoxy)-5-(tetrahydro-2''H-pyran-2''-yloxy)-2H-pyran (389860-55-3)

Guidance literature:

diethoxyphosphoryl-acetic acid ethyl ester; With sodium hydride; In tetrahydrofuran; at 0 ℃;

(2S,3S,6R)-6-(4-Methoxy-phenoxy)-3-(tetrahydro-pyran-2-yloxy)-3,6-dihydro-2H-pyran-2-carbaldehyde; In tetrahydrofuran; at -20 - 0 ℃; Further stages.;

DOI:10.1039/b104341m

Reference yield:

[(2R,3S,6R)-6-(4-Methoxy-phenoxy)-3-(tetrahydro-pyran-2-yloxy)-3,6-dihydro-2H-pyran-2-yl]-methanol → (2R,5S,6R,1'E,2''RS)-5,6-dihydro-6-(2'-ethoxycarbonyleth-1'-enyl)-2-(p-methoxyphenoxy)-5-(tetrahydro-2''H-pyran-2''-yloxy)-2H-pyran (389860-55-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 3 h / -30 - 0 °C

2.1: NaH / tetrahydrofuran / 0 °C

2.2: 4.50 g / tetrahydrofuran / -20 - 0 °C

With oxalyl dichloride; sodium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; 1.1: Swern oxidation;

DOI:10.1039/b104341m

Reference yield: 84.0%

(2R,5S,6R,1'E,2''RS)-5,6-dihydro-6-(2'-ethoxycarbonyleth-1'-enyl)-2-(p-methoxyphenoxy)-5-(tetrahydro-2''H-pyran-2''-yloxy)-2H-pyran (389860-55-3) → (2R,5S,6R,1'E)-6-(3'-hydroxyprop-1'-enyl)-5,6-dihydro-2-(p-methoxyphenoxy)-5-(tetrahydro-2''H-pyran-2''-yloxy)-2H-pyran (389860-56-4)

Guidance literature:

With diisobutylaluminium hydride; In diethyl ether; at -78 ℃; for 1h;

DOI:10.1039/b104341m

upstream raw materials:

diethoxyphosphoryl-acetic acid ethyl ester

Downstream raw materials:

(2R,5S,6R,1'E)-6-(3'-hydroxyprop-1'-enyl)-5,6-dihydro-2-(p-methoxyphenoxy)-5-(tetrahydro-2''H-pyran-2''-yloxy)-2H-pyran

(2R,5S,6R,1'E)-6-(but-1'-enyl)-5,6-dihydro-2-(p-methoxyphenoxy)-5-(tetrahydro-2''H-pyran-2''-yloxy)-2H-pyran

(2R,5S,6R,1'E)-6-(3'-acetoxyprop-1'-enyl)-5,6-dihidro-2-(p-methoxyphenoxy)-5-(tetrahydro-2''H-pyran-2''-yloxy)-2H-pyran