394739-29-8

Basic information

• Product Name: 2-(acetoxymethyl)-5-oxotetrahy drofuran-3,4-diyl diacetate
• Synonyms: 2-(acetoxymethyl)-5-oxotetrahy drofuran-3,4-diyl diacetate
• CAS NO: 394739-29-8
• Molecular Formula: C11H14O8
• Molecular Weight: 274
• Mol File: 394739-29-8.mol

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-(acetoxymethyl)-5-oxotetrahy drofuran-3,4-diyl diacetate(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(acetoxymethyl)-5-oxotetrahy drofuran-3,4-diyl diacetate(394739-29-8)
• EPA Substance Registry System: 2-(acetoxymethyl)-5-oxotetrahy drofuran-3,4-diyl diacetate(394739-29-8)

Safety Data

• Hazardous Substances Data: 394739-29-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-(acetoxymethyl)-5-oxotetrahydrofuran-3,4-diyl diacetate is used as a precursor in the synthesis of various medications due to its reactivity and functional groups. Its ability to form esters makes it a valuable component in the development of new pharmaceutical compounds.
Used as an Intermediate in Organic Synthesis:
In the realm of organic chemistry, 2-(acetoxymethyl)-5-oxotetrahydrofuran-3,4-diyl diacetate serves as an intermediate for the production of other organic compounds. Its versatile structure allows it to be a key component in creating a wide range of chemical products.
Used as a Solvent in Chemical Reactions:
2-(acetoxymethyl)-5-oxotetrahydrofuran-3,4-diyl diacetate can also be utilized as a solvent in certain chemical reactions. Its solubility in organic solvents makes it suitable for facilitating various chemical processes, particularly in the synthesis of complex organic molecules.

Upstream product

• 87-72-9 D-Xylose 
• 108-24-7 acetic anhydride 
• 15384-34-6 D-lyxono-1,4-lactone 
• 2782-09-4 DL-arabinonic acid-4-lactone 
• 82796-87-0 D-xylono-1,5-lactone 
• 5461-96-1 ammonium D-xylonate 
• 64-19-7 acetic acid 
• 15384-37-9 D-xylono-1,4-lactone 
• 51532-86-6 L-arabino-1,4-lactone 
• 532-20-7 D-Ribose 
• 108-05-4 vinyl acetate 
• 5336-08-3 D-Ribono-1,4-lactone 
• 84044-87-1 methyl (3R,4R)-2,2-dichloro-4,5-O-isopropylidene-3,4,5-trihydroxypentanoate 
• 288103-33-3 1-[1-C-Phenylseleno-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-ribo-pentofuranosyl]uracil 

Relevant articles and documents

Molecular sieves mediated green per-O-acetylation of carbohydrate templates and lipase catalyzed regioselective alcoholysis of 2,3,5-Tri-O-acetyl-D-ribonolactone

The per-O-acetylation of D-ribono-1,4-lactone and representative carbohydrates through the combination of acetic anhydride and molecular sieves under solvent-free conditions is demonstrated. The use of 13X/KCl molecular sieves as the heterogeneous catalyst was found to be more efficient than the excess of pyridine normally employed in the conventional method, giving high yields of the expected peracetylated product after 3 h at 25 °C or 1 h at 50 °C. The transformation can be carried out in gram scale and in an open flask. Additionally, the catalyst is readily separated from the reaction medium and can be reutilized without significant loss of activity. This green procedure for acetylation was extended to D-ribonolactone derivatives and natural carbohydrates. To demonstrate the synthetic utility of the method, 2,3,5-tri-O-acetyl-D-ribonolactone was selected as the substrate for the regioselective alcoholysis of acetyl group catalyzed by Candida antarctica lipase B in EtOH to selectively produce 2,3-di-O-acetyl-D-ribonolactone in gram scale.

Regioselective acylation of d-ribono-1,4-lactone catalyzed by lipases

Lipases from ten different sources and two mycelium-bound lipases isolated from Amazonian fungi were screened as biocatalysts in the acylation reaction of d-ribono-1,4-lactone with a variety of acyl donors in non-aqueous media. Several reaction parameters were evaluated including the type and amount of enzyme, acyl donor, and organic solvent, as well as the influence of water and the recyclability of the catalyst. When Candida antarctica lipase (CAL-B) was used, the acylation was highly regioselective and the corresponding 5-acyl-d-ribono-1,4-lactones were observed as the sole product. The best conversion (>99%) into 5-acetyl-d-ribono-1,4-lactone was obtained through the combination of vinyl acetate as the acetyl donor and 10 mg (100 U) of CAL-B in dry acetonitrile after 24 h. However, lipases from Burkholderia cepacia (PSL-C and PSL-D), Pseudomonas fluorescens (AK) and Thermomyces langinosus (Lipozyme TL-IM) gave mixtures of mono-, di- and tri-acetylated products in lower conversions. CAL-B maintained its catalytic activity during five cycles of repeated use when decanoic and dodecanoic acids were employed as acyl donors in the acylation of d-ribono-1,4-lactone.

2,3-Anhydrosugars in glycoside bond synthesis: Mechanism of 2-deoxy-2-thioaryl glycoside formation

A series of investigations probing the mechanism of the 2,3-anhydrosugar migration - glycosylation reaction were performed using a thioglycoside with the D-lyxo stereochemistry as the substrate. Among the work reported are the results of quantum mechanical calculations, NMR studies, the measurement of α-deuterium kinetic isotope effects, and the synthesis of a series of substrate analogues. All studies point to a consistent finding: that the reaction proceeds through an oxocarbenium ion intermediate, not an episulfonium ion as previously suggested. It is proposed that the high stereoselectivity of the reaction arises from a preferred "inside attack" of the nucleophile onto the oxocarbenium ion intermediate.

A chiron approach to the total synthesis of (+)-aculeatin D

(Chemical Equation Presented) A synthesis of natural aculeatin D has been achieved, with the key stereogenic centers taken from inexpensive and readily available D-xylose. In elaboration of D-xylose into a desired form readily applicable in synthesis a pr

Synthesis of 1′-fluorouracil nucleosides as potential antimetabolites

The first synthesis of 1′-fluoronucleosides, which has long been synthetic targets as the potential antimetabolites, was achieved. Electrophilic fluorination of the 1′-position occurred to form an anomeric mixture of 1′-fluorouridine derivatives, when the

Synthesis of two novel chiral building blocks for anti- And syn-1,3-diols

Two novel chiral building blocks 1 and 2 for anti- and syn-1,3-diols have been synthesized starting from the readily available and inexpensive D-(+)-xylose.

Stereocontrol in organic synthesis using silicon-containing compounds. Syntheses of (±)-2-deoxyribonolactone and (±)-arabonolactone

Samarium iodide reacts with methyl (Z)-3-dimethyl(4-methylphenyl)silylprop-2-enoate 5b to give dimethyl (3RS,4SR)-3,4-bis[dimethyl(4-methylphenyl)silyl]hexane-1,6-dioate 8b with high stereoselectivity. This meso diester can be converted into (3RS,4SR)-3,4-bis[dimethyl(4-methylphenyl)silyl]pentan-5-olide 16 by Dieckmann cyclisation, demethoxycarbonylation and Baeyer-Villiger reaction. Silyl-to-hydroxy conversion and relactonisation gave (±)-deoxyribonolactone, and anti-selective enolate hydroxylation followed by silyl-to-hydroxy conversion gave (±)-arabonolactone. An attempt to synthesise sugars with the relative configuration (3RS,4RS) was thwarted by an unprecedented retention of configuration at the migration origin in the cationic rearrangement of (3RS,4SR)-3,4-bis[dimethyl(4-methylphenyl)silyl]-5-hydroxypentanoic acid 28 to (3RS,4SR)-3,5-bis[dimethyl(4-methylphenyl)silyl]pentan-1,4-olide 30.

A General Synthetic Route to A-Ring Hydroxylated Vitamin D Analogs from Pentoses

The enyne needed for coupling to a CD-ring fragment, namely, 3S,5R-oct-1-en-7-yne-3,5-diol, in the Trost-Dumas carbopalladation route to 1α,25-dihydroxyvitamin D3 was synthesized from D-xylose in 13 steps and 21percent yield.

Stereoselective Samarium(II)-induced Coupling of β-Silylacrylic Esters: a Synthesis of (+/-)-2-Deoxyribonolactone

Samarium iodide converts the β-silylacrylate 1c with high stereoselectivity into the racemic diester 2c, from which (+/-)deoxyribonolactone 11 can be prepared.