(1S,2S,3S,5R,8R,10S,11R,12R)-2-(acetoxymethyl)-3-methoxy-8-phenyl-4,7,9-trioxatetracyclo[10.2.1.0^2,11.0^5,10]pentadec-13-ene

Base Information

• Chemical Name: (1S,2S,3S,5R,8R,10S,11R,12R)-2-(acetoxymethyl)-3-methoxy-8-phenyl-4,7,9-trioxatetracyclo[10.2.1.0^2,11.0^5,10]pentadec-13-ene
• CAS No.: 959842-64-9
• Molecular Formula: C₂₂H₂₆O₆
• Molecular Weight: 386.445

Synonyms:(1S,2S,3S,5R,8R,10S,11R,12R)-2-(acetoxymethyl)-3-methoxy-8-phenyl-4,7,9-trioxatetracyclo[10.2.1.0^2,11.0^5,10]pentadec-13-ene

Chemical Property of (1S,2S,3S,5R,8R,10S,11R,12R)-2-(acetoxymethyl)-3-methoxy-8-phenyl-4,7,9-trioxatetracyclo[10.2.1.0^2,11.0^5,10]pentadec-13-ene

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Technology Process of (1S,2S,3S,5R,8R,10S,11R,12R)-2-(acetoxymethyl)-3-methoxy-8-phenyl-4,7,9-trioxatetracyclo[10.2.1.0^2,11.0^5,10]pentadec-13-ene

There total 1 articles about (1S,2S,3S,5R,8R,10S,11R,12R)-2-(acetoxymethyl)-3-methoxy-8-phenyl-4,7,9-trioxatetracyclo[10.2.1.0^2,11.0^5,10]pentadec-13-ene 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: 91.0%

(1S,2S,3S,5R,8R,10S,11R,12R)-2-(hydroxymethyl)-3-methoxy-8-phenyl-4,7,9-trioxatetracyclo[10.2.1.02,11.05,10]pentadec-13-ene (959842-63-8) + acetic anhydride (108-24-7) → (1S,2S,3S,5R,8R,10S,11R,12R)-2-(acetoxymethyl)-3-methoxy-8-phenyl-4,7,9-trioxatetracyclo[10.2.1.02,11.05,10]pentadec-13-ene (959842-64-9)

Guidance literature:

With pyridine; dmap; In dichloromethane; at 0 - 20 ℃;

DOI:10.1016/j.tet.2007.08.070

Reference yield:

methanol (67-56-1) + (1S,2S,3S,5R,8R,10S,11R,12R)-2-(acetoxymethyl)-3-methoxy-8-phenyl-4,7,9-trioxatetracyclo[10.2.1.02,11.05,10]pentadec-13-ene (959842-64-9) → C23H28O9 + C23H28O9

Guidance literature:

methanol; (1S,2S,3S,5R,8R,10S,11R,12R)-2-(acetoxymethyl)-3-methoxy-8-phenyl-4,7,9-trioxatetracyclo[10.2.1.0^2,11.0^5,10]pentadec-13-ene; With sodium hydrogencarbonate; ozone; In dichloromethane; at -78 ℃;

With acetic anhydride; triethylamine; In dichloromethane; at 20 ℃; for 1h; Further stages. Title compound not separated from byproducts.;

DOI:10.1016/j.tet.2007.08.070

Reference yield:

methanol (67-56-1) + (1S,2S,3S,5R,8R,10S,11R,12R)-2-(acetoxymethyl)-3-methoxy-8-phenyl-4,7,9-trioxatetracyclo[10.2.1.02,11.05,10]pentadec-13-ene (959842-64-9) → C23H30O9 + (1R,2S,4R,7R,9S,10R,11S,13R)-1-(acetoxymethyl)-11-(hydroxymethyl)-2-methoxy-7-phenyl-3,6,8-trioxatricyclo[8.3.0.04,9]tridecane-13-carboxylic acid methyl ester

Guidance literature:

methanol; (1S,2S,3S,5R,8R,10S,11R,12R)-2-(acetoxymethyl)-3-methoxy-8-phenyl-4,7,9-trioxatetracyclo[10.2.1.0^2,11.0^5,10]pentadec-13-ene; With sodium hydrogencarbonate; ozone; In dichloromethane; at -78 ℃;

With acetic anhydride; triethylamine; In dichloromethane; at 20 ℃; for 1h;

With sodium tetrahydroborate; In methanol; dichloromethane; at 0 ℃; for 0.25h; Further stages.;

DOI:10.1016/j.tet.2007.08.070

upstream raw materials:

(1S,2S,3S,5R,8R,10S,11R,12R)-2-(hydroxymethyl)-3-methoxy-8-phenyl-4,7,9-trioxatetracyclo[10.2.1.0^2,11.0^5,10]pentadec-13-ene

acetic anhydride

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