(+)-Goniofufurone

Base Information

• Chemical Name: (+)-Goniofufurone
• CAS No.: 129578-06-9
• Molecular Formula: C₁₃H₁₄O₅
• Molecular Weight: 250.251
• DSSTox Substance ID: DTXSID301317805
• Nikkaji Number: J934.720H
• Wikidata: Q105191837
• Metabolomics Workbench ID: 122568
• ChEMBL ID: CHEMBL1171386
• Mol file: 129578-06-9.mol

Synonyms:7-epi-goniofufurone;7-goniofufurone;goniofufurone

Chemical Property of (+)-Goniofufurone

Chemical Property:

• XLogP3: 0.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 250.08412354
• Heavy Atom Count: 18
• Complexity: 325

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1C2C(C(C(O2)C(C3=CC=CC=C3)O)O)OC1=O
• Isomeric SMILES: C1[C@@H]2[C@@H]([C@H]([C@H](O2)[C@@H](C3=CC=CC=C3)O)O)OC1=O

Technology Process of (+)-Goniofufurone

There total 126 articles about (+)-Goniofufurone 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: 98.6%

(3aR,5R,6S,6aS)-6-(tert-Butyl-diphenyl-silanyloxy)-5-((R)-hydroxy-phenyl-methyl)-tetrahydro-furo[3,2-b]furan-2-one (913174-83-1) → (+)-goniofufurone (136778-39-7,144015-82-7,144829-37-8,129578-06-9)

Guidance literature:

With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; at 0 ℃; for 0.0833333h;

DOI:10.1039/b713070h

Reference yield: 97.0%

3,6-anhydro-5-O-benzyl-2-deoxy-7-C-phenyl-D-glycero-D-ido-heptono-1,4-lactone (956317-01-4) → (+)-goniofufurone (136778-39-7,144015-82-7,144829-37-8,129578-06-9)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃; for 46h;

DOI:10.1016/j.tet.2009.10.079

Reference yield: 91.0%

3,6-anhydro-2-deoxy-7-C-phenyl-L-idohept-7-ulosono-1,4-lactone → (+)-goniofufurone (136778-39-7,144015-82-7,144829-37-8,129578-06-9) + (+)-7-epi-goniofufurone

Guidance literature:

With sodium tetrahydroborate; L-Tartaric acid; In tetrahydrofuran; at -18 ℃; for 20h;

DOI:10.1016/j.ejmech.2014.05.081

upstream raw materials:

(S)-5-((1S,2R,3R)-1,2,3-trihydroxy-3-phenylpropyl)furan-2(5H)-one

6R,7R,8S-7-benzyloxy-1,5-dioxa-6-(R-benzyloxybenzyl)-2-oxobicyclo<3.3.0.>oct-3-ene

3,6-anhydro-5,7-di-O-benzyl-2-deoxy-7-C-phenyl-D-glycero-D-ido-heptono-1,4-lactone

(+)-(1'S,2'R,3'R,4R)-4-(1',2',3'-trihydroxy-3'-phenylpropyl)-2-buten-4-olide

Downstream raw materials:

(R)-((2R,3S,3aS,6aR)-3-(cinnamoyloxy)-5-oxo-hexahydrofuro[3,2-b]furan-2-yl)(phenyl)methyl cinnamate

Refernces

• 1、 Mukai, Chisato,Kim, In Jong,Hanaoka, Miyoji. "An optically active chromium(0)-complexed benzaldehyde derivative in organic synthesis: A highly stereocontrolled total synthesis of (+)-goniofufurone". . p. 6081 - 6082. Retrieved 1993.
• 2、 Prakash,Prahlada Rao. "Ethoxycarbonylmethylenetriphenylphosphorane in carbohydrate chemistry, part II: A short and efficient synthesis of (+)-goniofufurone". . p. 1505 - 1510. Retrieved 1993.
• 3、 Ralph, Michael,Ng, Sean,Booker-Milburn, Kevin I.. "Short Flow-Photochemistry Enabled Synthesis of the Cytotoxic Lactone (+)-Goniofufurone". . p. 968 - 971. Retrieved 2016/03/15.
• 4、 Pal, Pinki,Shaw, Arun K.. "Stereoselective total syntheses of (+)-exo- and (-)-exo-brevicomins, (+)-endo- and (-)-endo-brevicomins, (+)- and (-)-cardiobutanolides, (+)-goniofufurone". experimental part. p. 4036 - 4047. Retrieved 2011/06/25.