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

Base Information

• Chemical Name: (1S,2S,3S,5R,8R,10S,11R,12R)-3-methoxy-8-phenyl-4,7,9-trioxatetracyclo[10.2.1.0^2,11.0^5,10]pentadec-13-ene-2-carbaldehyde
• CAS No.: 911053-15-1
• Molecular Formula: C₂₀H₂₂O₅
• Molecular Weight: 342.392

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

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

Chemical Property:

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

There total 1 articles about (1S,2S,3S,5R,8R,10S,11R,12R)-3-methoxy-8-phenyl-4,7,9-trioxatetracyclo[10.2.1.0^2,11.0^5,10]pentadec-13-ene-2-carbaldehyde 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: 26.0%

methyl 4,6-O-benzylidene-2,3-dideoxy-2-C-formyl-α-D-erythro-hex-2-enopyranoside (845669-58-1) + cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) → (1S,2S,3S,5R,8R,10S,11R,12R)-3-methoxy-8-phenyl-4,7,9-trioxatetracyclo[10.2.1.02,11.05,10]pentadec-13-ene-2-carbaldehyde (911053-15-1)

Guidance literature:

With lithium perchlorate; In Petroleum ether; at 20 ℃; for 168h;

DOI:10.1016/j.tetasy.2006.06.006

Reference yield: 100.0%

(1S,2S,3S,5R,8R,10S,11R,12R)-3-methoxy-8-phenyl-4,7,9-trioxatetracyclo[10.2.1.02,11.05,10]pentadec-13-ene-2-carbaldehyde (911053-15-1) → (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)

Guidance literature:

With sodium tetrahydroborate; In methanol; dichloromethane; at 0 ℃; for 0.666667h;

DOI:10.1016/j.tet.2007.08.070

Reference yield: 54.0%

(1S,2S,3S,5R,8R,10S,11R,12R)-3-methoxy-8-phenyl-4,7,9-trioxatetracyclo[10.2.1.02,11.05,10]pentadec-13-ene-2-carbaldehyde (911053-15-1) + methanol (67-56-1) + acetic anhydride (108-24-7) → (1R,2S,3S,5R,8R,10S,11R,12S,14R,15S)-12-[(acetoxy)(methoxy)methyl]-3-methoxy-8-phenyl-4,7,9,16,17,18-hexaoxapentacyclo[13.2.1.02,11.02,14.05,10]octadecane

Guidance literature:

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

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

DOI:10.1016/j.tet.2007.08.070

upstream raw materials:

methyl 4,6-O-benzylidene-2,3-dideoxy-2-C-formyl-α-D-erythro-hex-2-enopyranoside

cyclopenta-1,3-diene

Downstream 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

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