(2'R,3Z,4'S,5'S)-4-(4',5'-dihydroxy-6'-oxotetrahydropyran-2'-yl)-3-butenyl benzoate

Base Information

• Chemical Name: (2'R,3Z,4'S,5'S)-4-(4',5'-dihydroxy-6'-oxotetrahydropyran-2'-yl)-3-butenyl benzoate
• CAS No.: 1042909-11-4
• Molecular Formula: C₁₆H₁₈O₆
• Molecular Weight: 306.315
• Mol file: 1042909-11-4.mol

Synonyms:(2'R,3Z,4'S,5'S)-4-(4',5'-dihydroxy-6'-oxotetrahydropyran-2'-yl)-3-butenyl benzoate

Chemical Property of (2'R,3Z,4'S,5'S)-4-(4',5'-dihydroxy-6'-oxotetrahydropyran-2'-yl)-3-butenyl benzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2'R,3Z,4'S,5'S)-4-(4',5'-dihydroxy-6'-oxotetrahydropyran-2'-yl)-3-butenyl benzoate

There total 4 articles about (2'R,3Z,4'S,5'S)-4-(4',5'-dihydroxy-6'-oxotetrahydropyran-2'-yl)-3-butenyl benzoate 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: 65.0%

methyl (2S,3S,5R,6Z)-6-benzoyloxy-5-hydroxy-2,3-isopropylidenedioxy-6-nonenoate (1042909-15-8) → methyl (2S,3S,5S,6E)-9-benzoyloxy-3-hydroxy-2,5-oxy-6-nonenoate (1042909-08-9) + methyl (2S,3S,5R,6E)-9-benzoyloxy-3-hydroxy-2,5-oxy-6-nonenoate (1042909-06-7) + (2'R,3Z,4'S,5'S)-4-(4',5'-dihydroxy-6'-oxotetrahydropyran-2'-yl)-3-butenyl benzoate (1042909-11-4) + methyl (2S,3S,5R,6Z)-9-benzoyloxy-2,3,5-trihydroxy-6-nonenoate (1042909-10-3)

Guidance literature:

With CuCl₂*2H₂O; In acetonitrile; at 20 ℃;

DOI:10.1021/jo800514k

Reference yield: 52.0%

methyl (2S,3S,5R,6Z)-5-acetoxy-9-benzoyloxy-2,3-isopropylidenedioxy-6-nonenoate (1042909-04-5) → (2'R,3Z,4'S,5'S)-4-(4',5'-dihydroxy-6'-oxotetrahydropyran-2'-yl)-3-butenyl benzoate (1042909-11-4) + methyl (2S,3S,5R,6E)-3-acetoxy-9-benzoyloxy-2,5-oxy-6-nonenoate (1042909-05-6) + methyl (2S,3S,5S,6E)-3-acetoxy-9-benzoyloxy-2,5-oxy-6-nonenoate (1042909-07-8) + methyl (2S,3S,5R,6Z)-5-acetoxy-9-benzoyloxy-2,3-dihydroxy-6-nonenoate (1042909-09-0)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 0 ℃; for 72h; Further byproducts.;

DOI:10.1021/jo800514k

Reference yield: 45.0%

methyl (2S,3S,5R,6Z)-5-acetoxy-9-benzoyloxy-2,3-isopropylidenedioxy-6-nonenoate (1042909-04-5) → (2'R,3Z,4'S,5'S)-4-(4',5'-dihydroxy-6'-oxotetrahydropyran-2'-yl)-3-butenyl benzoate (1042909-11-4) + methyl (2S,3S,5R,6Z)-9-benzoyloxy-2,3,5-trihydroxy-6-nonenoate (1042909-10-3) + methyl (2S,3S,5R,6Z)-5-acetoxy-9-benzoyloxy-2,3-dihydroxy-6-nonenoate (1042909-09-0)

Guidance literature:

With Dowex resin H⁽¹⁺⁾; In methanol; water; at 20 ℃; for 72h;

DOI:10.1021/jo800514k

upstream raw materials:

methyl (2S,3S,5R,6Z)-5-acetoxy-9-benzoyloxy-2,3-isopropylidenedioxy-6-nonenoate

methyl (2S,3S,5R,6Z)-9-benzoyloxy-2,3,5-trihydroxy-6-nonenoate

methyl (2S,3S,5R,6Z)-6-benzoyloxy-5-hydroxy-2,3-isopropylidenedioxy-6-nonenoate