136778-39-7

Basic information

• Product Name: 7-goniofufurone
• Synonyms: 7-goniofufurone
• CAS NO: 136778-39-7
• Molecular Formula: C₁₃H₁₄O₅
• Molecular Weight: 250.24726
• Mol File: 136778-39-7.mol

Chemical Properties

• Melting Point: 192-193 °C
• Boiling Point: 527.1°Cat760mmHg
• Flash Point: 208.5°C
• Appearance: /
• Density: 1.429g/cm³
• Vapor Pressure: 6.12E-12mmHg at 25°C
• Refractive Index: 1.618
• PKA: 13.15±0.40(Predicted)
• CAS DataBase Reference: 7-goniofufurone(CAS DataBase Reference)
• NIST Chemistry Reference: 7-goniofufurone(136778-39-7)
• EPA Substance Registry System: 7-goniofufurone(136778-39-7)

Safety Data

• Hazardous Substances Data: 136778-39-7(Hazardous Substances Data)

Usage

InChI:InChI=1/C13H14O5/c14-9-6-8-12(18-9)11(16)13(17-8)10(15)7-4-2-1-3-5-7/h1-5,8,10-13,15-16H,6H2/t8-,10?,11-,12+,13-/m1/s1

Upstream product

• 142955-65-5 (S)-5-((1S,2R,3R)-1,2,3-trihydroxy-3-phenylpropyl)furan-2(5H)-one 
• 147697-41-4 3,6-anhydro-5,7-di-O-benzyl-2-deoxy-7-C-phenyl-D-glycero-D-ido-heptono-1,4-lactone 
• 153000-33-0 (+)-(1'S,2'R,3'R,4R)-4-(1',2',3'-trihydroxy-3'-phenylpropyl)-2-buten-4-olide 
• 956317-01-4 3,6-anhydro-5-O-benzyl-2-deoxy-7-C-phenyl-D-glycero-D-ido-heptono-1,4-lactone 
• 96405-62-8 (5S,6R)-6-[(1S,2R)-1-(benzyloxy)-1,2-dihydroxy-2-phenylethyl]-5-hydroxy-5,6-dihydro-2H-pyran-2-one 
• 2033-24-1 cycl-isopropylidene malonate 
• 252273-48-6 trimethyl (4R,5R,6S,7R)-7-(t-butyldimethylsilyloxy)-5,6-isopropylidenedioxy-3-phenylsulfonyl-7-phenylorthoheptanoate 
• 844473-76-3 methyl (4R,4aR,6R,7S,7aS)-2-(7-methoxymethoxy-2,2-dimethyl-4-phenyltetrahydrofuro[3,2-d][1,3]-dioxin-6-yl)acetate 
• 677300-65-1 (4R,5R,6R)-5-(tert-butyldimethylsilyloxy)-4-[(1S)-2-(tert-butyldimethylsilyloxy)-1-benzoyloxyethyl]-2,2-dimethyl-6-phenyl-[1,3]dioxane 
• 844473-75-2 (4R,4aR,6R,7S,7aS)-6-allyl-7-methoxymethoxy-2,2-dimethyl-4-phenyl-tetrahydrofuro[3,2-d][1,3]-dioxine 
• 844473-73-0 (2S)-2-[(4R,5R,6R)-5-(tert-butyldimethylsilyloxy)-2,2-dimethyl-6-phenyl-[1,3]dioxan-4-yl]-2-(methoxymethoxy)ethanol 
• 844473-74-1 (1S,2S)-1-[(4R,5R,6R)-5-(tert-butyldimethylsilyloxy)-2,2-dimethyl-6-phenyl-[1,3]dioxan-4-yl]-1-(methoxymethoxy)pent-4-en-2-ol 
• 214678-58-7 (4R)-4-t-butyldimethylsilyloxy-4-phenyl-2S,3S-O-isopropylidene-butanol 
• 187931-99-3 ethyl (4S,5S)-5-[(R)-{[(tert-butyl)(dimethyl)silyl]oxy}(phenyl)methyl]-2,2-dimethyl-1,3-dioxolane-4-carboxylate 

Downstream Products

• 129578-09-2 diacetylgoniofufurone 
• 1262487-80-8 (R)-((2R,3S,3aS,6aR)-3-(cinnamoyloxy)-5-oxo-hexahydrofuro[3,2-b]furan-2-yl)(phenyl)methyl cinnamate 

Relevant articles and documents

A concise synthesis of (+)-goniofufurone, (+)-7-epi-goniofufurone, (+)-crassalactones B and C

The concise and efficient synthesis of (+)-goniofufurone, (+)-7-epi-goniofufurone, (+)-crassalactones B and C were achieved in 6 to 7 steps from the known D-glucono-δ-lactone derivative 9. An acid-mediated cascade cyclization was employed to construct the

Short Flow-Photochemistry Enabled Synthesis of the Cytotoxic Lactone (+)-Goniofufurone

A photochemical approach to the cytotoxic lactone (+)-goniofufurone (1) is reported. Paternò-Büchi [2 + 2] photocycloaddition from known enol ether 4, derived from the readily available sugar d-isosorbide, yielded oxetane 7. This slow, dilute reaction was

Conformationally constrained goniofufurone mimics as inhibitors of tumour cells growth: Design, synthesis and SAR study

Synthesis of conformationally restricted (+)-goniofufurone (1) and 7-epi-(+)-goniofufurone (2) analogues, with embedded O-isopropylidene, O-methylidene or cyclic carbonate functions is disclosed starting from d-glucose. A number of potential bioisosteres

Stereoselective total syntheses of (+)-exo- and (-)-exo-brevicomins, (+)-endo- and (-)-endo-brevicomins, (+)- and (-)-cardiobutanolides, (+)-goniofufurone

Stereoselective total syntheses of aggregation pheromones (+)-exo-brevicomin (9a), (-)-exo-brevicomin (9b), (+)-endo-brevicomin (9c), (-)-endo-brevicomin (9d) and styryllactones (+)-cardiobutanolide (14a), (-)-cardiobutanolide (14b), and (+)-goniofufurone

Stereoselective total synthesis of styryl-lactones: (+)-crassalactones B and C, (+)-howiionol A, (+)-tricinnamate, (+)-goniofufurone and (+)-dicinnamoyl goniofufurone

The total synthesis of (+)-crassalactone B, (+)-crassalactone C, (+)-howiionol A, (+)-tricinnamate, (+)-goniofufurone, and (+)-dicinnamoyl goniofufurone is achieved by a 'chiron approach' starting from diacetone d-glucose (DAG). Mitsunobu inversion, Wittig olefination and ring closing metatheses were used as key steps for (+)-howiionol A and (+)-tricinnamate. Meldrum's acid was used for the synthesis of (+)-crassalactone C, (+)-goniofufurone, and (+)-dicinnamoyl goniofufurone. Yamaguchi esterification was used for (+)-crassalactone B, while a Grignard reaction followed by concomitant deallylation was first reported in the synthesis of (+)-dicinnamoyl goniofufurone.

Design, synthesis and antiproliferative activity of styryl lactones related to (+)-goniofufurone

This paper describes a straightforward divergent synthesis of (+)-goniofufurone mimics (4, 5 and 6) starting from d-xylose. In a preliminary bioassay, analogues 4 and 5 exhibited a submicromolar antiproliferative activity towards HL-60 cells, while the co

Enantiodivergent synthesis of cytotoxic styryl lactones from d-xylose. The first total synthesis of (+)- and (-)-crassalactone C

Enantiodivergent total syntheses of both (+)- and (-)-enantiomers of goniofufurone, 7-epi-goniofufurone and crassalactone C have been accomplished starting from d-xylose. The key steps of the synthesis of 7-epi-(+)-goniofufurone were a stereo-selective ad

Total syntheses of (+)-7-epi-goniofufurone, (+)-goniopypyrone and (+)-goniofufurone from a common precursor

Total syntheses of (+)-7-epi-goniofufurone, (+)-goniopypyrone and (+)-goniofufurone have been achieved from an advanced common precursor formed from d-(+)-mannitol by changing the carbinol protection profile. The Royal Society of Chemistry.

Divergent synthesis of cytotoxic styryl lactones from D-xylose. The first total synthesis of (+)-crassalactone C

A new divergent approach to (+)-goniofufurone (1) and 7-epi-(+)- goniofufurone (2), as well as the first total synthesis of crassalactone C (3), has been achieved starting from o-xylose. In a preliminary bioassay, all three natural products 1, 2, and 3 sh

SULFUR-mediated synthesis of substituted tetrahydrofurans: Application to the synthesis of goniofufurone

An efficient strategy for the synthesis of densely functionalized 2,5-trans-disubstituted-tetrahydrofurans (4), from sulfmyldienols is described. Further transformations of this substrate have resulted in a new synthesis of goniofufurone (1) by means of s