56543-10-3

Basic information

• Product Name: 2,3-O-Isopropylidene-D-lyxono-1,4-lactone
• Synonyms: 2,3-O-Isopropylidene-D-lyxono-1,4-lactone;2,3-O-Isopropylidene-D-lyxonic acid-1,4-lactone;2,3-O-(1-Methylethylidene)-
• CAS NO: 56543-10-3
• Molecular Formula: C₈H₁₂O₅
• Molecular Weight: 188.17788
• Product Categories: Carbohydrates & Derivatives;Inhibitors
• Mol File: 56543-10-3.mol
• Article Data: 12

Chemical Properties

• Appearance: /
• Storage Temp.: Refrigerator
• Solubility: Acetone (Slightly), Chloroform (Slightly),
• CAS DataBase Reference: 2,3-O-Isopropylidene-D-lyxono-1,4-lactone(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-O-Isopropylidene-D-lyxono-1,4-lactone(56543-10-3)
• EPA Substance Registry System: 2,3-O-Isopropylidene-D-lyxono-1,4-lactone(56543-10-3)

Safety Data

• Hazardous Substances Data: 56543-10-3(Hazardous Substances Data)

Usage

Uses

Intermediate in the synthesis of the α-L-fucosidase inhibitor, Deoxyfuconojirimycin

Upstream product

• 1128-23-0 L-gulono-1,4-lactone 
• 7306-64-1 2,3:5,6-di-O-isopropylidene-L-gulonolactone 
• 94840-08-1 2,3-O-isopropylidene-L-gulono-γ-lactone 
• 94840-09-2 (3aS,4S,6aS)-2,2-Dimethyl-6-oxo-tetrahydro-furo[3,4-d][1,3]dioxole-4-carbaldehyde 
• 77-76-9 2,2-dimethoxy-propane 
• 5336-08-3 D-Ribono-1,4-lactone 
• 50-69-1 D-ribose 
• 67-64-1 acetone 
• 15384-34-6 D-lyxono-1,4-lactone 
• 78138-87-1 potassium D-lyxonate 
• 1114-34-7 D-lyxose 
• 10257-28-0 D-Galactose 
• 116669-78-4 (4S,5S)-2,2-dimethyl-5-vinyl-[1,3]dioxolane-4-carbaldehyde 
• 127666-07-3 4,5-Dideoxy-2,3-O-isopropylidene-L-erythro-pent-4-enoic acid 

Downstream Products

• 4099-88-1 2,3-O-isopropylidene-L-ribofuranose 
• 114817-96-8 (4S,5R)-2,2-dimethyl-4-hydroxymethyl-5-vinyl-1,3-dioxolane 
• 99902-66-6 4,5-dideoxy-2,3-O-isopropylidene-D-erythro-pent-4-enonic acid 
• 1442089-72-6 5-O-benzhydryl-2,3-O-isopropylidene-D-lyxono-1,4-lactone 
• 1442089-83-9 2-C-azidomethyl-2,3,5-tri-O-benzyl-D-lyxitol 
• 1442089-81-7 2-C-azidomethyl-2,3,5-tri-O-benzyl-D-lyxono-1,4-lactone 
• 1442089-78-2 2-C-azidomethyl-5-O-benzhydryl-2,3-O-isopropylidene-D-lyxono-1,4-lactone 
• 1442089-77-1 5-O-benzhydryl-2-C-hydroxymethyl-2,3-O-isopropylidene-D-lyxono-1,4-lactone 
• 1442089-87-3 2-C-azidomethyl-2,3,5-tri-O-benzyl-1-O-tert-butyldimethylsilyl-4-O-methanesulfonyl-D-lyxitol 
• 1442089-85-1 2-C-azidomethyl-2,3,5-tri-O-benzyl-1-O-tert-butyldimethylsilyl-Dlyxitol 
• 848909-11-5 Allyl-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-1-((4R,5R)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-ethyl]-carbamic acid benzyl ester 
• 849372-33-4 4-(tert-butyl-dimethyl-silanyloxymethyl)-7,8-dihydroxy-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-c]azepine-5-carboxylic acid benzyl ester 
• 849372-28-7 (3aS,4R,7S,8S,8aR)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-7,8-dihydroxy-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-c]azepine-5-carboxylic acid benzyl ester 
• 849372-35-6 (3aS,4S,6aS,9aS,9bS)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2,8,8-tetramethyl-hexahydro-1,3,7,9-tetraoxa-5-aza-cyclopenta[e]azulene-5-carboxylic acid benzyl ester 

Relevant articles and documents

High-Yielding Diastereoselective syn-Dihydroxylation of Protected HBO: An Access to D-(+)-Ribono-1,4-lactone and 5-O-Protected Analogues

A diastereoselective chemoenzymatic synthetic pathway to D-(+)-ribono-1,4-lactone, a versatile chiral sugar derivative widely used for the synthesis of various natural products, has been designed from cellulose-based levoglucosenone (LGO). This route involves a sustainable Baeyer-Villiger oxidation of LGO to produce enantiopure (S)-γ-hydroxymethyl-α,β-butenolide (HBO) that is further functionalized with various protecting groups to provide 5-O-protected γ-hydroxymethyl-α,β-butenolides. The latter then undergo a diastereoselective and high-yielding syn-dihydroxylation of the α,β-unsaturated lactone moiety followed by a deprotection step to give D-(+)-ribono-1,4-lactone. Through this 4-step synthetic route from LGO, D-(+)-ribono-1,4-lactone is obtained with d.r. varying from 82:18 to 97:3 and in overall yields between 32 and 41 % depending on the protecting group used. Moreover, valuable synthetic intermediates 5-O-tert-butyldimethylsilyl-, 5-O-tert-butyldiphenylsilyl- as well as 5-O-benzyl-ribono-1,4-lactones are obtained in 3 steps from LGO in 58, 61 and 40 %, respectively.

Evaluation of fluoropyruvate as nucleophile in reactions catalysed by N-acetyl neuraminic acid lyase variants: Scope, limitations and stereoselectivity

The catalysis of reactions involving fluoropyruvate as donor by N-acetyl neuraminic acid lyase (NAL) variants was investigated. Under kinetic control, the wild-type enzyme catalysed the reaction between fluoropyruvate and N-acetyl mannosamine to give a 90-10 ratio of the (3R,4R)- and (3S,4R)-configured products; after extended reaction times, equilibration occurred to give a 30-70 mixture of these products. The efficiency and stereoselectivity of reactions of a range of substrates catalysed by the E192N, E192N/T167V/S208V and E192N/T167G NAL variants were also studied. Using fluoropyruvate and (2R,3S)- or (2S,3R)-2,3-dihydroxy-4-oxo-N,N-dipropylbutanamide as substrates, it was possible to obtain three of the four possible diastereomeric products; for each product, the ratio of anomeric and pyranose/furanose forms was determined. The crystal structure of S. aureus NAL in complex with fluoropyruvate was determined, assisting rationalisation of the stereochemical outcome of C-C bond formation.

D-ribonolactone and 2,3-isopropylidene(D-ribonolactone): (D-Ribonic acid, 2,3-O-(1-methylethylidene)-, -lactone)

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