Succinic acid mono-((3R,3aS,5R,5aS,8aR)-5-benzyloxy-6-oxo-5-pentyl-tetrahydro-difuro[3,2-b;3',4'-c]furan-3-yl) ester

Base Information

• Chemical Name: Succinic acid mono-((3R,3aS,5R,5aS,8aR)-5-benzyloxy-6-oxo-5-pentyl-tetrahydro-difuro[3,2-b;3',4'-c]furan-3-yl) ester
• CAS No.: 186265-11-2
• Molecular Formula: C₂₄H₃₀O₉
• Molecular Weight: 462.497

Synonyms:Succinic acid mono-((3R,3aS,5R,5aS,8aR)-5-benzyloxy-6-oxo-5-pentyl-tetrahydro-difuro[3,2-b;3',4'-c]furan-3-yl) ester

Chemical Property of Succinic acid mono-((3R,3aS,5R,5aS,8aR)-5-benzyloxy-6-oxo-5-pentyl-tetrahydro-difuro[3,2-b;3',4'-c]furan-3-yl) ester

Chemical Property:

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Technology Process of Succinic acid mono-((3R,3aS,5R,5aS,8aR)-5-benzyloxy-6-oxo-5-pentyl-tetrahydro-difuro[3,2-b;3',4'-c]furan-3-yl) ester

There total 3 articles about Succinic acid mono-((3R,3aS,5R,5aS,8aR)-5-benzyloxy-6-oxo-5-pentyl-tetrahydro-difuro[3,2-b;3',4'-c]furan-3-yl) ester 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: 96.0%

succinic acid anhydride (108-30-5) + (3R,3aS,5R,5aS,8aR)-5-Benzyloxy-3-hydroxy-5-pentyl-tetrahydro-difuro[3,2-b;3',4'-c]furan-6-one (186265-00-9) → Succinic acid mono-((3R,3aS,5R,5aS,8aR)-5-benzyloxy-6-oxo-5-pentyl-tetrahydro-difuro[3,2-b;3',4'-c]furan-3-yl) ester (186265-11-2)

Guidance literature:

With dmap; In chloroform-d1; for 72h;

DOI:10.1016/S0031-9422(96)00530-4

Reference yield:

syringolide 1 (147716-82-3) → Succinic acid mono-((3R,3aS,5R,5aS,8aR)-5-benzyloxy-6-oxo-5-pentyl-tetrahydro-difuro[3,2-b;3',4'-c]furan-3-yl) ester (186265-11-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / Dowex 50W-X₈*HCl / CH₂Cl₂

2: 96 percent / 4-dimethylaminopyridine / CDCl₃ / 72 h

With dmap; Dowex 50W-X₈*HCl; In chloroform-d1; dichloromethane;

DOI:10.1016/S0031-9422(96)00530-4

Reference yield:

benzyl alcohol (100-51-6,185532-71-2) → Succinic acid mono-((3R,3aS,5R,5aS,8aR)-5-benzyloxy-6-oxo-5-pentyl-tetrahydro-difuro[3,2-b;3',4'-c]furan-3-yl) ester (186265-11-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / Dowex 50W-X₈*HCl / CH₂Cl₂

2: 96 percent / 4-dimethylaminopyridine / CDCl₃ / 72 h

With dmap; Dowex 50W-X₈*HCl; In chloroform-d1; dichloromethane;

DOI:10.1016/S0031-9422(96)00530-4

upstream raw materials:

succinic acid anhydride

(3R,3aS,5R,5aS,8aR)-5-Benzyloxy-3-hydroxy-5-pentyl-tetrahydro-difuro[3,2-b;3',4'-c]furan-6-one

syringolide 1

benzyl alcohol

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