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

Base Information

• Chemical Name: methyl (2S,3S,5R,6Z)-5-acetoxy-9-benzoyloxy-2,3-isopropylidenedioxy-6-nonenoate
• CAS No.: 1042909-04-5
• Molecular Formula: C₂₂H₂₈O₈
• Molecular Weight: 420.46
• Mol file: 1042909-04-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about methyl (2S,3S,5R,6Z)-5-acetoxy-9-benzoyloxy-2,3-isopropylidenedioxy-6-nonenoate 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: 73.0%

methyl (2S,3S,5R)-5-acetoxy-2,3-isopropylidenedioxy-6-oxohexanoate (1042909-00-1) + bromure de benzoyloxy-3 propyltriphenylphosphonium (30698-18-1) → methyl (2S,3S,5R,6Z)-5-acetoxy-9-benzoyloxy-2,3-isopropylidenedioxy-6-nonenoate (1042909-04-5)

Guidance literature:

bromure de benzoyloxy-3 propyltriphenylphosphonium; With 18-crown-6 ether; potassium carbonate; In tetrahydrofuran; for 1h; Heating;

methyl (2S,3S,5R)-5-acetoxy-2,3-isopropylidenedioxy-6-oxohexanoate; In tetrahydrofuran; Further stages.; Heating;

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)-5-acetoxy-2,3-isopropylidenedioxy-6-oxohexanoate

bromure de benzoyloxy-3 propyltriphenylphosphonium

Downstream raw materials:

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

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

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

methyl (2S,3S,5R,6E)-3-acetoxy-9-benzoyloxy-2,5-oxy-6-nonenoate