96422-52-5

Basic information

• Product Name: (6R)-6-[(1R,2R)-1,2-Dihydroxy-2-phenylethyl]-5,6-dihydro-2H-pyran-2-one
• Synonyms: (+)-Goniodiol;(6R)-6-[(1R,2R)-1,2-Dihydroxy-2-phenylethyl]-5,6-dihydro-2H-pyran-2-one;Goniodiol
• CAS NO: 96422-52-5
• Molecular Formula: C₁₃H₁₄O₄
• Molecular Weight: 234.24786
• Mol File: 96422-52-5.mol
• Article Data: 26

Chemical Properties

• Boiling Point: 488.2°C at 760 mmHg
• Flash Point: 192.1°C
• Appearance: /
• Density: 1.306g/cm³
• Vapor Pressure: 2.41E-10mmHg at 25°C
• Refractive Index: 1.597
• CAS DataBase Reference: (6R)-6-[(1R,2R)-1,2-Dihydroxy-2-phenylethyl]-5,6-dihydro-2H-pyran-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (6R)-6-[(1R,2R)-1,2-Dihydroxy-2-phenylethyl]-5,6-dihydro-2H-pyran-2-one(96422-52-5)
• EPA Substance Registry System: (6R)-6-[(1R,2R)-1,2-Dihydroxy-2-phenylethyl]-5,6-dihydro-2H-pyran-2-one(96422-52-5)

Safety Data

• Hazardous Substances Data: 96422-52-5(Hazardous Substances Data)

Usage

General Description

"(6R)-6-[(1R,2R)-1,2-Dihydroxy-2-phenylethyl]-5,6-dihydro-2H-pyran-2-one" is a chemical compound with the molecular formula C13H16O4. It is a pyranone derivative with a chiral center at the 6th carbon atom, resulting in two enantiomers. (6R)-6-[(1R,2R)-1,2-Dihydroxy-2-phenylethyl]-5,6-dihydro-2H-pyran-2-one has a pyran ring and a phenylethyl group, as well as two hydroxy groups attached to the chiral center. It is commonly used in organic synthesis and medicinal chemistry, where its unique structure and properties make it a valuable building block for producing complex molecules and pharmaceuticals. Additionally, its potential biological activities and pharmaceutical applications make it a target for further research and development.

InChI:InChI=1/C13H14O4/c14-11-8-4-7-10(17-11)13(16)12(15)9-5-2-1-3-6-9/h1-6,8,10,12-13,15-16H,7H2/t10-,12-,13+/m1/s1

Upstream product

• 891491-87-5 Z-(2R,2'R)-trimethyl-[1-phenyl-2-(6'-tert-butyldiphenylsilanyloxymethylpyran-2'-yloxy)-vinyloxy]-silane 
• 216769-17-4 (4R,5S,2'R,6'R)-2,2-dimethyl-5-(6'-tert-butyldiphenylsilanyloxymethylpyran-2'-yl)-4-phenyl-[1,3]dioxolane 
• 891491-88-6 (1R,2R)-1-[(2R,6R)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-tetrahydro-pyran-2-yl]-2-phenyl-ethane-1,2-diol 
• 216769-40-3 (R,R)-N-methoxy-N-methyl-2-(6'-tert-butyldiphenylsilanyloxymethylpyranyloxy)-acetamide 
• 216769-05-0 (R,R)-2-(6'-tert-butyldiphenylsilanyloxymethylpyranyloxy)-1-phenylethanone 
• 891491-89-7 (6R,4'S,5'R)-6-(2',2'-dimethyl-5'-phenyl-[1',3']dioxolan-4'-yl)-3-phenylselanyltetrahydropyran-2-one 
• 216769-01-6 (R)-6-(tert-butyldiphenylsilanyloxymethyl)-tetrahydropyran-2-ol 
• 216769-55-0 (6R,4'S,5'R) 6-(2',2'-dimethyl-5'-phenyl-[1',3']dioxolan-4'-yl)-pyranyl acetate 
• 216769-22-1 (2R,6R)-6-((4S,5R)-2,2-Dimethyl-5-phenyl-[1,3]dioxolan-4-yl)-tetrahydro-pyran-2-carboxylic acid 
• 216769-45-8 (4R,5S,2'R,6'R)-2,2-dimethyl-5-(6'-hydroxymethylpyran-2'-yl)-4-phenyl-[1,3]dioxolane 
• 216769-50-5 (2R,6R,4'S,5'R)-6-(2',2'-dimethyl-5'-phenyl-[1,3]dioxolan-4'-yl)-pyran-2-carbaldehyde 
• 216769-61-8 (R)-6-((4S,5R)-2,2-Dimethyl-5-phenyl-[1,3]dioxolan-4-yl)-tetrahydro-pyran-2-ol 
• 216769-26-5 (6R,4'S,5'R)-6-(2',2'-dimethyl-5'-phenyl-[1',3']dioxolan-4'-yl)-pyran-2-one 
• 473980-86-8 (Z)-(5R,6S,7R)-5,6,7-Trihydroxy-7-phenyl-hept-2-enoic acid methyl ester 

Downstream Products

• 96422-53-6 (6R,7R,8R)-goniodiol-7-monoacetate 
• 144429-71-0 (6R,7R,8R)-goniodiol-8-monoacetate 
• 194355-09-4 (R)-6-((1R,2S)-1-Benzyloxy-2-hydroxy-2-phenyl-ethyl)-5,6-dihydro-pyran-2-one 
• 194355-10-7 (-)-(1R,5R,7S,8R)-8-benzyloxy-7-phenyl-2,6-dioxabicyclo[3.3.1]nonan-3-one 
• 136685-37-5 (1R,5R,7S,8S)-8-hydroxy-7-phenyl-2,6-dioxa-bicyclo-[3.3.1]-nonan-3-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 
• 136778-40-0 7,8-di-O-acetyl-goniodiol 

Relevant articles and documents

Biosynthesis-Inspired Total Synthesis of Bioactive Styryllactones (+)-Goniodiol, (6S,7S,8S)-Goniodiol, (-)-Parvistone D, and (+)-Parvistone e

A protecting-group-free total synthesis of (+)-goniodiol (1), (6S,7S,8S)-goniodiol (2), (-)-parvistone D (4), and (+)-parvistone E (6) was efficiently achieved in five steps from commercially available trans-cinnamaldehyde with high overall yields (72-75%). The synthesis strategy was inspired from the proposed biosynthesis pathway of styryllactones. Key transformations of the strategy include a one-pot conversion of goniothalamin oxide to goniodiol or 9-deoxygoniopypyrone in aqueous media, stereoselective epoxidation, ring-closing metathesis, and stereoselective Maruoka allylation. The route is amenable to synthesis of various analogues for biological evaluation.

An efficient total synthesis of (+)-goniodiol

An efficient total synthesis of (+)-goniodiol was illustrated by using Carreira alkynylation and Sharpless asymmetric dihydroxylation as key steps. Georg Thieme Verlag Stuttgart New York.

Stereoselective total synthesis of leiocarpin C and (+)-goniodiol

Total syntheses of styryl lactones, leiocarpin C and (+)-goniodiol have been accomplished in a highly stereoselective manner. The key steps involved in these syntheses are the Chan alkyne reduction, Sharpless asymmetric dihydroxylation, Horner-Wadsworth-E