cis-3-(benzoyloxy)-2-<3-(benzyloxy)-1-(E)-propenyl>-2,3-dihydropyran-4-one

Base Information

• Chemical Name: cis-3-(benzoyloxy)-2-<3-(benzyloxy)-1-(E)-propenyl>-2,3-dihydropyran-4-one
• CAS No.: 118893-65-5
• Molecular Formula: C₂₂H₂₀O₅
• Molecular Weight: 364.398

Synonyms:cis-3-(benzoyloxy)-2-<3-(benzyloxy)-1-(E)-propenyl>-2,3-dihydropyran-4-one

Chemical Property of cis-3-(benzoyloxy)-2-<3-(benzyloxy)-1-(E)-propenyl>-2,3-dihydropyran-4-one

Chemical Property:

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Technology Process of cis-3-(benzoyloxy)-2-<3-(benzyloxy)-1-(E)-propenyl>-2,3-dihydropyran-4-one

There total 2 articles about cis-3-(benzoyloxy)-2-<3-(benzyloxy)-1-(E)-propenyl>-2,3-dihydropyran-4-one 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:

4-benzyloxycrotonaldehyde (69152-87-0) + 1-methoxy-3-((tert-butyldimethylsilyl)oxy)-4-(benzoyloxy)-1,3-butadiene (87461-94-7) → trans-3-(benzyloxy)-2-<3-(benzyloxy)-1-(E)-propenyl>-2,3-dihydropyran-4-one (118893-65-5) + cis-3-(benzoyloxy)-2-<3-(benzyloxy)-1-(E)-propenyl>-2,3-dihydropyran-4-one (118893-65-5)

Guidance literature:

With boron trifluoride diethyl etherate; trifluoroacetic acid; Yield given. Multistep reaction; 1.) dichloromethane, -78 deg C, 5.5 h, 2.) carbon tetrachloride;

DOI:10.1021/ja00188a038

Reference yield:

4-benzyloxycrotonaldehyde (69152-87-0) + 1-methoxy-3-((tert-butyldimethylsilyl)oxy)-4-(benzoyloxy)-1,3-butadiene (87461-94-7) → trans-3-(benzyloxy)-2-<3-(benzyloxy)-1-(E)-propenyl>-2,3-dihydropyran-4-one (118893-65-5) + cis-3-(benzoyloxy)-2-<3-(benzyloxy)-1-(E)-propenyl>-2,3-dihydropyran-4-one (118893-65-5)

Guidance literature:

With boron trifluoride diethyl etherate; trifluoroacetic acid; Yield given. Multistep reaction; 1.) dichloromethane, -78 deg C, 5.5 h, 2.) carbon tetrachloride;

DOI:10.1021/ja00188a038

Reference yield: 86.0%

cis-3-(benzoyloxy)-2-<3-(benzyloxy)-1-(E)-propenyl>-2,3-dihydropyran-4-one (118893-65-5) → Benzoic acid (2R,3R,4R)-2-((E)-3-benzyloxy-propenyl)-4-hydroxy-3,4-dihydro-2H-pyran-3-yl ester (118893-66-6)

Guidance literature:

With sodium tetrahydroborate; cerium(III) chloride; In methanol; ethanol; at -78 ℃; for 1h;

DOI:10.1021/ja00188a038

upstream raw materials:

4-benzyloxycrotonaldehyde

1-methoxy-3-((tert-butyldimethylsilyl)oxy)-4-(benzoyloxy)-1,3-butadiene

Downstream raw materials:

Benzoic acid (2R,3R,4R)-2-((E)-3-benzyloxy-propenyl)-4-hydroxy-3,4-dihydro-2H-pyran-3-yl ester

Benzoic acid (R)-2-((E)-3-benzyloxy-propenyl)-4-(tert-butyl-dimethyl-silanyloxy)-3,4-dihydro-2H-pyran-3-yl ester

Benzoic acid (3S,4R,5R)-2-((S)-3-benzyloxy-1,2-dihydroxy-propyl)-4-(tert-butyl-dimethyl-silanyloxy)-5,6-dihydroxy-tetrahydro-pyran-3-yl ester

Benzoic acid (3S,4R,5R,6R)-2-((R)-3-benzyloxy-1,2-dihydroxy-propyl)-4-(tert-butyl-dimethyl-silanyloxy)-5,6-dihydroxy-tetrahydro-pyran-3-yl ester

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