204975-45-1

Basic information

• Product Name: 4,7-ANHYDRO-2,3-DIDEOXY-7R-C-PHENYL-D-XYLO-HEPTONIC ACID, METHYL ESTER
• Synonyms: (+)-GONIOTHALESDIOL;4,7-ANHYDRO-2,3-DIDEOXY-7R-C-PHENYL-D-XYLO-HEPTONIC ACID, METHYL ESTER;RUDVTXZKYPJLFH-AHLTXXRQSA-N
• CAS NO: 204975-45-1
• Molecular Formula: C₁₄H₁₈O₅
• Molecular Weight: 266.28972
• Mol File: 204975-45-1.mol

Chemical Properties

• Boiling Point: 429.5±45.0 °C(Predicted)
• Appearance: /
• Density: 1.256±0.06 g/cm3(Predicted)
• PKA: 13.59±0.70(Predicted)
• CAS DataBase Reference: 4,7-ANHYDRO-2,3-DIDEOXY-7R-C-PHENYL-D-XYLO-HEPTONIC ACID, METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 4,7-ANHYDRO-2,3-DIDEOXY-7R-C-PHENYL-D-XYLO-HEPTONIC ACID, METHYL ESTER(204975-45-1)
• EPA Substance Registry System: 4,7-ANHYDRO-2,3-DIDEOXY-7R-C-PHENYL-D-XYLO-HEPTONIC ACID, METHYL ESTER(204975-45-1)

Safety Data

• Hazardous Substances Data: 204975-45-1(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 158673-96-2 (2R,3R,3aS,7aS)-tetrahydro-3-hydroxy-2-phenyl-2H-furo[3,2-b]pyran-5(6H)-one 
• 1220627-90-6 methyl (4R,5S,6R,7R)-4-chloro-5,6,7-trihydroxy-7-phenylheptanoate 
• 476153-93-2 (1S,5S,7R,8R)-8-hydroxy-7-phenyl-2,6-dioxabicyclo[3.3.0]octan-3-one 
• 476153-89-6 (R)-((4R,5R)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)(phenyl)methanol 
• 476153-91-0 (1R,2S,3R)-1-phenyl-pent-4-ene-1,2,3-triol 
• 3969-59-3 mannitol triacetonide 
• 69-65-8 mannitol 
• 168109-89-5 (1R)-1-((4R,5R)-2,2-dimethyl-5-vinyl[1,3]dioxolan-4-yl)ethane-1,2-diol 
• 607375-99-5 ethyl 3,4-dihydroxy-5-phenyl-(2R,3S,4S,5R)-tetrahydro-2-furancarboxylate 
• 869733-55-1 methyl 3-[3,4-di-tert-butyldimethylsilanyloxy-5-phenyl-(2S,3R,4R,5R)-tetrahydro-2-furanyl]-(Z)-2-propenoate 
• 869733-51-7 ethyl 3,4-di-tert-butyldimethylsilanyloxy-5-phenyl-(2R,3R,4R,5R)-tetrahydro-2-furancarboxylate 
• 1002753-33-4 (2R,3R,4R,5R)-3,4-bis(tert-butyldimethylsiloxy)-5-phenyltetrahydrofuran-2-carbaldehyde 
• 869733-37-9 methyl 3-[3,4-di-tert-butyldimethylsilanyloxy-5-phenyl-(2S,3R,4R,5R)-tetrahydro-2-furanyl]-propanoate 

Relevant articles and documents

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"Chemical Equation Presented" What a (strain) relief! The first broadly applicable, catalytic, and stereoselective vinyl oxirane ring expansion is described (see scheme; hfacac = hexafluoroacetylacetonate). The stereoselectivity was influenced by several reaction parameters, and kinetic studies support a mechanistic proposal involving the in situ formation of a more reactive catalytic species. This ring-expansion reaction has been employed in the asymmetric total synthesis of (+)-goniothalesdiol.

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Stereoselective total synthesis of (+)-goniothalesdiol and (+)-2,5-epi-goniothalesdiol from D-mannitol

An efficient and practical total synthesis of (+)-goniothalesdiol and its 2,5-epi analogue is described herein. The key features include a diastereoselective reduction of C-5 keto with Zn(BH4)2 to generate the desired stereochemistry

Stereoselective synthesis of (+)-goniothalesdiol

Stereoselective synthesis of antitumor tetrahydrofuran (+)-goniothalesdiol was achieved in high overall yield from (-)-D-tartaric acid. Key features include an FeCl3 mediated THF formation with very high selectivity. Synthesis of natural gonith

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A total synthesis of (+)-goniothalesdiol, a 3,4-dihydroxy-2,5-disubstituted tetrahydrofuran isolated from Goniothalamus borneensis (Annonaceae), and its 7-epimer is reported using oxycarbonylation methodology for construction of polyhydroxylated substitut

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A flexible stereoselective route to synthesize both enantiomers of the highly functionalized substituted tetrahydrofurans and α,β- unsaturated-δ-lactones, goniothales diol, altholactone, and isoaltholactone, from readily available cinnamyl alcohol is described. This approach derived its asymmetry from Sharpless catalytic asymmetric epoxidation and Sharpless asymmetric dihydroxylation reactions. The resulting diols were produced in high enantiomeric excess and were cyclized in a stereoselective manner in the presence of a catalytic amount of camphor sulfonic acid.

The first total synthesis of goniothalesdiol

The first total synthesis of goniothalesdiol, a dihydroxylated tetrahydrofuran isolated from Goniothalamus borneensis (Annonaceae), and its 7-epimer is described starting with D-mannitol. The key step of these syntheses is palladium(II)-catalyzed oxycarbo