23339-15-3

Basic information

• Product Name: ethyl 2,3-dideoxy-D-hex-2-enopyranoside
• Synonyms: ethyl 2,3-dideoxy-D-hex-2-enopyranoside;Ethyl 2,3-dideoxy-α-D-erythro-2-hexenopyranoside
• CAS NO: 23339-15-3
• Molecular Formula: C₈H₁₄O₄
• Molecular Weight: 174.19436
• Mol File: 23339-15-3.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 316.9°Cat760mmHg
• Flash Point: 145.5°C
• Appearance: /
• Density: 1.19g/cm³
• Vapor Pressure: 3.34E-05mmHg at 25°C
• Refractive Index: 1.509
• CAS DataBase Reference: ethyl 2,3-dideoxy-D-hex-2-enopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 2,3-dideoxy-D-hex-2-enopyranoside(23339-15-3)
• EPA Substance Registry System: ethyl 2,3-dideoxy-D-hex-2-enopyranoside(23339-15-3)

Safety Data

• Hazardous Substances Data: 23339-15-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C8H14O4/c1-2-11-8-4-3-6(10)7(5-9)12-8/h3-4,6-10H,2,5H2,1H3

Upstream product

• 56932-85-5 ethyl 4,6-di-O-benzoyl-2,3-dideoxy-α-D-threo-hex-2-enopyranoside 
• 4098-06-0 triacetyl-D-galactal 
• 69055-68-1 ethyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-threo-hex-2-enopyranoside 
• 63976-48-7 ethyl 4,6-di-O-acetyl-2,3-dideoxy-α,β-D-threo-hex-2-enopyranoside 
• 3323-72-6 ethyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythrohex-2-enopyranoside 

Downstream Products

• 51172-44-2 ethyl-[bis-O-(4-nitro-benzoyl)-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside] 
• 81303-38-0 Ethyl-4,6-di-O-tosyl-2,3-didesoxy-α-D-erythro-hex-2-enopyranosid 
• 175877-47-1 (2R,3S,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-ethoxy-3,6-dihydro-2H-pyran-3-ol 
• 39798-87-3 ethyl 4,6-di-O-benzyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside 
• 871584-79-1 ethyl 4-O-acetyl-6-O-benzyl-2,3-dideoxyhex-2-enopyranoside 
• 871584-83-7 ethyl 6-O-benzyl-4-O-(ethylcarbonate)-2,3-dideoxyhex-2-enopyranoside 
• 871584-81-5 ethyl 6-O-benzyl-4-O-(ethylcarbonate)-2,3-dideoxyhex-2-enopyranoside 
• 871584-82-6 ethyl 6-O-benzyl-4-O-trifluoroacetyl-2,3-dideoxyhex-2-enopyranoside 
• 871584-84-8 ethyl 6-O-benzyl-4-O-trifluoroacetyl-2,3-dideoxyhex-2-enopyranoside 
• 871584-80-4 ethyl 4-O-benzoyl-6-O-benzyl-2,3-dideoxyhex-2-enopyranoside 
• 151807-90-8 ethyl 4-O-benzoyl-6-O-benzyl-2,3-dideoxy-α-D-threo-hex-2-enopyranoside 
• 130645-57-7 ethyl 6-O-benzyl-2,3-dideoxy-α-D-threo-hex-2-enopyranoside 
• 52471-76-8 ethyl 2,3-dideoxy-α-D-threo-hex-2-enopyranoside 
• 40555-08-6 ethyl 2,3-dideoxy-6-O-trityl-α-D-glycero-hex-2-enopyranosid-4-ulose 

Relevant articles and documents

Efficient pseudo-enantiomeric carbohydrate olefin ligands

Highly efficient pseudo-enantiomeric olefin ligands were designed from d-glucose and d-galactose. These ligands yield consistently excellent levels of enantioselectivity in Rh(I)-catalyzed 1,4-additions of aryl- and alkenylboronic acids to achiral enones and high diastereoselectivity with chiral substrates. Contrary to established olefin ligands, they are obtained enantiomerically pure via short syntheses without racemic resolution steps, making them a valuable addition to the arsenal of chiral ligands with olefinic donor sites.

The design and synthesis of novel anomeric hydroperoxides: Influence of the carbohydrate residue in the enantioselective epoxidation of quinones

We present a study of the base (DBU)-catalysed epoxidation of a number of important naturally occurring quinones using a series of pyranose-derived anomeric hydroperoxides. The absolute (viz. d or l) stereochemistry of the carbohydrate, electronic nature of the 6-substituent and ring substitution are all important variables, both for the formation of the hydroperoxide and its reactivity. Reactions studied were the epoxidation of a precursor of the natural antibiotic, alisamycin and a series of naphthoquinones related to Vitamin K. In the best case, an ee of 82% was obtained; either product enantiomer is accessible according to the absolute stereochemistry of the carbohydrate. Finally, a molecular modelling study of the reaction is reported, concluding that the reactions are under kinetic control and that the observed ees cannot be explained by considering transition states that involve only the quinone and peroxide anion. It seems likely that the DBU molecule may play a key role in the transition state.

Cis-oxyamination routes to amino sugars: A simple synthesis of holacosamine

-