94324-23-9

Usage

Uses

Used in Pharmaceutical Industry:
5-BROMO-5-DEOXY-2,3-O-ISOPROPYLIDENE-D-RIBONOLACTONE is used as a key intermediate for the synthesis of pharmaceutical compounds, particularly those with chiral centers. Its optical activity and unique structure enable the development of enantiomerically pure drugs, which are essential for ensuring the desired therapeutic effects and minimizing side effects.
Used in Chemical Synthesis:
5-BROMO-5-DEOXY-2,3-O-ISOPROPYLIDENE-D-RIBONOLACTONE is used as a versatile building block in the synthesis of various organic compounds, including chiral molecules, pharmaceuticals, and agrochemicals. Its reactivity and functional groups allow for a wide range of chemical transformations, making it a valuable component in the development of new and innovative chemical products.
Used in Research and Development:
5-BROMO-5-DEOXY-2,3-O-ISOPROPYLIDENE-D-RIBONOLACTONE is used as a research compound in the study of asymmetric synthesis, chiral chemistry, and the development of new synthetic methods. Its unique properties and reactivity make it an ideal candidate for exploring novel reaction pathways and discovering new synthetic strategies.
Used in Analytical Chemistry:
5-BROMO-5-DEOXY-2,3-O-ISOPROPYLIDENE-D-RIBONOLACTONE can be used as a reference compound in analytical chemistry for the development and validation of chiral separation techniques, such as chromatography and capillary electrophoresis. Its optical activity and unique structure make it a suitable candidate for evaluating the performance of these methods in the analysis of enantiomers.
Used in Material Science:
5-BROMO-5-DEOXY-2,3-O-ISOPROPYLIDENE-D-RIBONOLACTONE can be used as a chiral dopant or building block in the development of new materials with unique properties, such as chiral polymers, liquid crystals, and chiral catalysts. Its optical activity and chemical reactivity can contribute to the creation of materials with enhanced performance and novel applications.

InChI:InChI=1/C8H11BrO4/c1-8(2)12-5-4(3-9)11-7(10)6(5)13-8/h4-6H,3H2,1-2H3/t4-,5-,6-/m1/s1

Upstream product

• 30725-00-9 2,3-O-isopropylidene-D-ribonic-γ-lactone 
• 67-64-1 acetone 
• 160456-85-9 5-bromo-5-deoxy-D-pentono-1,4-lactone 
• 5336-08-3 D-Ribono-1,4-lactone 

Downstream Products

• 99902-66-6 4,5-dideoxy-2,3-O-isopropylidene-D-erythro-pent-4-enonic acid 
• 239784-28-2 (3S,4S,5R)-3-amino-5-benzyloxy-N-[(1S)-1-(tert-butoxycarbonyl)-3-methylbutyl]-4-hydroxypiperidin-2-one 
• 239784-37-3 (S)-2-((3R,4S,5R)-5-Benzyloxy-3,4-dihydroxy-2-oxo-piperidin-1-yl)-4-methyl-pentanoic acid tert-butyl ester 
• 239784-38-4 (3S,4S,5R)-3-azido-5-benzyloxy-N-[(1S)-1-(tert-butoxycarbonyl)-3-methylbutyl]-4-hydroxypiperidin-2-one 
• 239784-36-2 (S)-2-((3aR,7R,7aR)-7-Benzyloxy-2,2-dimethyl-4-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyridin-5-yl)-4-methyl-pentanoic acid tert-butyl ester 
• 138946-55-1 (1R,2R,3S,4R)-4-(benzyloxyamino)-2,3-O-isopropylidenecyclopentane-1,2,3-triol 
• 138946-45-9 5-bromo-2,3-O-isopropylidene-2,3,4-trihydroxypentanal-O-benzyl oxime 
• 155300-64-4 (1R,2R,3S,4R)-4-Benzyloxyamino-cyclopentane-1,2,3-triol 
• 94324-33-1 (3aS,4R,6S,6aS)-6-(2-ethoxy-2-oxoethyl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl benzoate 
• 94424-53-0 (3aS,4R,6R,6aS)-6-(2-ethoxy-2-oxoethyl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl benzoate 
• 94324-29-5 Benzoic acid (S)-2-bromo-1-[(4S,5S)-5-((Z)-2-ethoxycarbonyl-vinyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethyl ester 
• 100017-25-2 (4S,5R)-2,2-dimethyl-4-(p-toluenesulfonyloxy)methyl-5-vinyl-1,3-dioxolane 
• 114817-96-8 (4S,5R)-2,2-dimethyl-4-hydroxymethyl-5-vinyl-1,3-dioxolane 

Relevant academic research and scientific papers

Studies on the chemoselectivity and diastereoselectivity of samarium(II) iodide mediated transformations of carbohydrate derived ω-halo-α,β- unsaturated easters

Some carbohydrate derived ω-bromo- and ω-iode- α,β-unsaturated esters were reduced with SmI2 under a variety of conditions. The chemoselectivity varies dramatically with the choice of solvent system, the identity of halogen atom, the type of ester used, the geometry of the double bond, and the oxygenation pattern of the substrate. The stereoselectivity of the SmI2 mediated reactions is also influenced by the reaction parameters.

An improved synthesis of 5-thio-D-ribose from D-ribono-1,4-lactone.

5-Thio-D-ribopyranose was synthesized from D-ribono-1,4-lactone (1) by two approaches: (i) 5-bromo-5-deoxy-D-ribono-1,4-lactone (2) was successively transformed into 5-bromo-5-deoxy, 5-S-acetyl-5-thio or 5-thiocyanato-D-ribofuranose derivatives; appropriate treatment then lead to 5-thio-D-ribopyranose (7) in 46-48% overall yield and; (ii) 2 was transformed into the 5-S-acetyl-5-thio-D-ribono-1,4-lactone derivative (11). Reduction and deprotection of 11 afforded 5-thio-D-ribopyranose (7) in 57% overall yield.

Convenient syntheses of orthogonally protected aminocyclopentitols from aldopentoses

Orthogonally protected aminocyclopentitols were synthesized from commercially available aldopentoses using a convenient three-step procedure that does not require protection of the free anomeric hydroxyl group of the starting carbohydrate. The synthesized compounds are important building blocks with potential use in medicinal chemistry and drug discovery.

Synthesis of (1R,2S,3R,4R)-2,3,4-Trihydroxycyclopentylamine from D-Ribonolactone

A seven-step procedure for the transformation of ribonolactone 3 into the aminotriol 12 can be effected in 28percent overall yield.

Synthesis of Optically Active Olefinic Building Blocks from D-Ribonolactone: Isopropylidene Derivatives of D-erythro-Pentenediol and -triol (cis-4-Substituted 5-Vinyldioxolanes)

Optically active D-erythro-pentenediol and triol acetonides 4-11 were prepared from D-ribonolactone 1, via the acid 4 and the alcohol 9 as key intermediates.Acetonides 4-11 are cis-4-substituted 5-vinyldioxolanes, both needed as standard model substrates

New Syntheses of Carbocycles from Carbohydrates. Cyclization of Radicals Derived from Unsaturated Halo Sugars.

The cyclization of radicals derived from unsaturated aldoses promises to constitute an efficient and general preparation of hydroxylated cyclopentane and cyclohexane derivatives.The first example of this powerful new strategy for the preparation of polyhy

Inhibition of Arabinose 5-Phosphate Isomerase. An Approach to the Inhibition of Bacterial Lipopolysaccharide Biosynthesis

Arabinose 5-phosphate (A5P) isomerase is a key enzyme in the biosynthesis of liposaccharide, an essential component of the outer membrane of Gram-negative bacteria.The mechanism of the isomerase is envisioned to involve an enediol intermediate.A series of