136685-37-5

Basic information

• Product Name: 9-deoxygoniopypyrone
• Synonyms: 9-deoxygoniopypyrone;(7S)-3,7-Anhydro-2,4-dideoxy-7-C-phenyl-D-xyloheptonic acid Delta-lactone
• CAS NO: 136685-37-5
• Molecular Formula: C₁₃H₁₄O₄
• Molecular Weight: 234.24786
• Mol File: 136685-37-5.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 476.9°Cat760mmHg
• Flash Point: 189.2°C
• Appearance: /
• Density: 1.298g/cm³
• Vapor Pressure: 6.66E-10mmHg at 25°C
• Refractive Index: 1.575
• CAS DataBase Reference: 9-deoxygoniopypyrone(CAS DataBase Reference)
• NIST Chemistry Reference: 9-deoxygoniopypyrone(136685-37-5)
• EPA Substance Registry System: 9-deoxygoniopypyrone(136685-37-5)

Safety Data

• Hazardous Substances Data: 136685-37-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C13H14O4/c14-11-7-9-6-10(17-11)12(15)13(16-9)8-4-2-1-3-5-8/h1-5,9-10,12-13,15H,6-7H2/t9-,10-,12+,13+/m1/s1

Upstream product

• 146236-73-9 (6R)-6-[(1R,2S)-1,2-dihydroxy-2-phenylethyl]-5,6-dihydro-2H-pyran-2-one 
• 22639-28-7 (R)-goniothalamin 
• 160226-44-8 (R)-(-)-γ-Hydroxymethyl-δ-valerolactone 
• 160154-84-7 (R)-5-formyl δ-valerolactone 
• 146236-73-9 (+)-goniodiol 
• 1006371-17-0 (1R)-1-[(4S,5S)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]but-3-en-1-yl prop-2-enoate 
• 474958-87-7 (1R)-1-[(4S,5S)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]but-3-en-1-ol 
• 146173-59-3 Acetic acid (2R,3S)-2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-6-oxo-3,6-dihydro-2H-pyran-3-yl ester 
• 221639-38-9 2,2-dimethyl-4-(2-furyl)hydroxymethyl-1,3-dioxolane 
• 194355-09-4 (R)-6-((1R,2S)-1-Benzyloxy-2-hydroxy-2-phenyl-ethyl)-5,6-dihydro-pyran-2-one 
• 194355-07-2 (R)-6-((1R,2R)-1-Benzyloxy-2-hydroxy-2-phenyl-ethyl)-5,6-dihydro-pyran-2-one 
• 194355-08-3 4-Nitro-benzoic acid (1S,2S)-2-benzyloxy-2-((R)-6-oxo-3,6-dihydro-2H-pyran-2-yl)-1-phenyl-ethyl ester 
• 194355-05-0 (R)-6-[(1S,2R)-1-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-ethyl]-3,6-dihydro-pyran-2-one 
• 194355-06-1 (R)-6-[(1S,2R)-1-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-ethyl]-5,6-dihydro-pyran-2-one 

Relevant articles and documents

Highly diastereoselective total syntheses of (+)-7-epigoniodiol, (-)-8-epigoniodiol, and (+)-9-deoxygoniopypyrone

An expedient concise total synthesis of (+)-7-epigoniodiol, (-)-8-epigoniodiol, and (+)-9-deoxygoniopypyrone is accomplished. The key transformations include a catalytic hydroxylation and base-mediated N-(acetyl)oxazolidinone addition reactions, which cou

Facile stereoselective syntheses of goniodiol, 8-epi-goniodiol and 9-deoxygoniopypyrone

Stereoselective syntheses of the bio-active styryllactones goniodiol and 9-deoxygoniopypyrone were accomplished from d-(-)-tartaric acid. The key step involves the elaboration of a γ-hydroxy butyramide to the styryllactones via high yielding stereoselecti

Chiral hetero Diels-Alder products by enantioselective and diastereoselective zirconium catalysis. Scope, limitation, mechanism, and application to the concise synthesis of (+)-prelactone C and (+)-9-deoxygoniopypyrone

Catalytic asymmetric hetero Diels-Alder (HDA) reactions using a chiral zirconium complex have been developed. The reactions of aldehydes with Danishefsky's dienes proceeded smoothly to afford the corresponding pyranone derivatives in high yields with high diastereo- and enantioselectivities in the presence of a chiral zirconium complex, which was prepared from zirconium tert-butoxide, (R)-3,3′-diiodobinaphthol or its derivative, a primary alcohol, and a small amount of water. It is noted that 2,3-trans-pyranone derivatives were obtained with remarkably high diastereo- and enantioselectivities in the reaction with 4-methyl Danishefsky's diene. This is the first example of catalytic asymmetric trans-selective hetero Diels-Alder reactions of aldehydes. Furthermore, asymmetric HDA reactions with 4-benzyloxy Danishefsky's dienes were conducted to afford 2,3-cis-pyranone derivatives in high selectivities. Isolation of an intermediate of this asymmetric hetero Diels-Alder reaction indicated that the reaction proceeded in a stepwise cycloaddition pathway. Finally, these catalytic, asymmetric hetero Diels-Alder reactions were successfully applied to concise syntheses of biologically important natural pyranone derivatives, (+)-Prelactone C and (+)-9- deoxygoniopypyrone.