2-((2S,4S,6S)-4-(4-methoxybenzyloxy)-6-phenyl-tetrahydro-2H-pyran-2-yl)-1-phenylethanone

Base Information

• Chemical Name: 2-((2S,4S,6S)-4-(4-methoxybenzyloxy)-6-phenyl-tetrahydro-2H-pyran-2-yl)-1-phenylethanone
• CAS No.: 1192712-72-3
• Molecular Formula: C₂₇H₂₈O₄
• Molecular Weight: 416.517
• Mol file: 1192712-72-3.mol

Synonyms:2-((2S,4S,6S)-4-(4-methoxybenzyloxy)-6-phenyl-tetrahydro-2H-pyran-2-yl)-1-phenylethanone

Chemical Property of 2-((2S,4S,6S)-4-(4-methoxybenzyloxy)-6-phenyl-tetrahydro-2H-pyran-2-yl)-1-phenylethanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-((2S,4S,6S)-4-(4-methoxybenzyloxy)-6-phenyl-tetrahydro-2H-pyran-2-yl)-1-phenylethanone

There total 18 articles about 2-((2S,4S,6S)-4-(4-methoxybenzyloxy)-6-phenyl-tetrahydro-2H-pyran-2-yl)-1-phenylethanone 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:

C27H30O4 → 2-((2S,4S,6S)-4-(4-methoxybenzyloxy)-6-phenyl-tetrahydro-2H-pyran-2-yl)-1-phenylethanone (1192712-72-3)

Guidance literature:

With sodium hydrogencarbonate; Dess-Martin periodane; In dichloromethane; at 0 - 20 ℃; for 3.5h; Inert atmosphere;

DOI:10.1055/s-0035-1561592

Reference yield:

C28H30O4 → 2-((2S,4S,6S)-4-(4-methoxybenzyloxy)-6-phenyl-tetrahydro-2H-pyran-2-yl)-1-phenylethanone (1192712-72-3)

Guidance literature:

C₂₈H₃₀O₄; With trichloroacetic acid; In tetrahydrofuran; hexane; acetone; at 20 ℃; Inert atmosphere;

With water; sodium hydrogencarbonate; In tetrahydrofuran; hexane; acetone; Saturated solution;

DOI:10.1021/jo901739y

Reference yield:

C16H28O3Si → 2-((2S,4S,6S)-4-(4-methoxybenzyloxy)-6-phenyl-tetrahydro-2H-pyran-2-yl)-1-phenylethanone (1192712-72-3)

Guidance literature:

Multi-step reaction with 14 steps

1.1: formic acid; (R)-Ru(η-6-mesitylene)-(R,R)-TsDPEN; triethylamine / dichloromethane / Inert atmosphere; Reflux

2.1: water; sodium hydrogencarbonate; sodium acetate; N-Bromosuccinimide / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

3.1: dmap; triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere

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

5.1: sodium acetate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / acetonitrile / 4 h / 20 °C / Inert atmosphere

6.1: dirhodium tetraacetate / dichloromethane / 3 h / Inert atmosphere; Reflux

7.1: water; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / toluene / 0.5 h / 0 °C

8.1: methanol / 3 h / Inert atmosphere; Reflux

9.1: sodium cyanoborohydride; hydrogenchloride / methanol; tetrahydrofuran; diethyl ether / 0.75 h / 0 - 20 °C / Inert atmosphere

9.2: 1 h / 75 °C / Inert atmosphere

10.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C / Inert atmosphere

10.2: 12 h / 20 °C / Inert atmosphere

11.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

12.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 3.5 h / 0 - 20 °C / Inert atmosphere

13.1: tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

14.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 3.5 h / 0 - 20 °C / Inert atmosphere

With hydrogenchloride; dmap; dirhodium tetraacetate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; N-Bromosuccinimide; formic acid; (R)-Ru(η-6-mesitylene)-(R,R)-TsDPEN; tetrabutyl ammonium fluoride; water; sodium acetate; sodium hydride; sodium cyanoborohydride; sodium hydrogencarbonate; Dess-Martin periodane; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; zinc; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; mineral oil; 1.1: |Noyori Asymmetric Hydrogenation / 2.1: |Achmatowicz Reaction / 7.1: |Rubottom Oxidation / 12.1: |Dess-Martin Oxidation / 13.1: |Grignard Reaction;

DOI:10.1055/s-0035-1561592

upstream raw materials:

ethyl 3-(2-furyl)-3-hydroxypropanoate