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D-GALACTONO-1,4-LACTONE, also known as a galactonolactone derived from D-galactonic acid, is a naturally occurring compound that plays a significant role in carbohydrate research. It is characterized by its unique chemical structure and properties, which make it a valuable component in various applications.

2782-07-2

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2782-07-2 Usage

Uses

Used in Carbohydrate Research:
D-GALACTONO-1,4-LACTONE is used as an elution compound for the purification process of exo-β-D-galactofuranosidase enzyme. This application is crucial in the field of carbohydrate research, as it aids in the isolation and characterization of enzymes that are essential for understanding the biochemistry and biological functions of carbohydrates.

Purification Methods

Crystallise the lactone from EtOH, aqueous EtOH, MeOH or EtOAc. It is also purified by passage through a column of Amberlite IR-120 (H+ form), and the effluent and washings are then freeze-dried [Wolfrom & Thompson Methods in Carbohydrate Chemistry I 67 1963, Academic Press]. The 5,6-O-isopropylidene-D-galactono-1,4-lactone is purified by chromatography (EtOAc) and has m 165-167o (from EtOH/hexane), and 167.5-168.5o (from Me2CO/*C6H6) [NMR: Copel & Stick Aust J Chem 31 1371 1978.] [Beilstein 18 III/IV 3026, 18/5 V 18.]

Check Digit Verification of cas no

The CAS Registry Mumber 2782-07-2 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,7,8 and 2 respectively; the second part has 2 digits, 0 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 2782-07:
(6*2)+(5*7)+(4*8)+(3*2)+(2*0)+(1*7)=92
92 % 10 = 2
So 2782-07-2 is a valid CAS Registry Number.
InChI:InChI=1/C6H10O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2-5,7-10H,1H2/t2-,3-,4-,5+/m1/s1

2782-07-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name D-galactono-1,4-lactone

1.2 Other means of identification

Product number -
Other names D-GALACTONOLACTONE

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:2782-07-2 SDS

2782-07-2Relevant articles and documents

Synthesis of a novel UDP-carbasugar as UDP-galactopyranose mutase inhibitor

El Bkassiny, Sandy,N'Go, Ines,Sevrain, Charlotte M.,Tikad, Abdellatif,Vincent, Stephane P.

supporting information, p. 2462 - 2465 (2014/05/20)

The multistep synthesis of a novel UDP-C-cyclohexene, designed as a high energy intermediate analogue of the UDP-galactopyranose mutase (UGM) catalyzed isomerization reaction, is reported. The synthesis of the central carbasugar involved the preparation of a galactitol derivative bearing two olefins necessary for the construction of the cyclohexene ring by a ring-closing metathesis as a key step. Further successive phosphonylation, deprotection, and UMP coupling provided the target molecule. The final molecule was assayed against UGM and compared with UDP-C-Galf, the C-glycosidic UGM substrate analogue.

A simple synthesis of D-galactono-1,4-lactone and key building blocks for the preparation of galactofuranosides

De Talance, Vincent Lemau,Thiery, Emilie,Eppe, Guillaume,Bkassiny, Sandy El,Mortier, Jeremie,Vincent, Stephane P.

experimental part, p. 605 - 617 (2012/06/04)

The oxidation of D-galactose by Br2 to yield D-galactono-1,4-lactone was developed and applied to the preparation of key building blocks for the synthesis of galactofuranosides. Three D-galactono-1,4-lactone derivatives protected as acetates, TBDMS ether, or acetonide were directly obtained in two steps on multigram scale with only one purification step. A mild deacetylation methodology afforded pure D-galactono-1,4-lactone and a new reduction of the lactone functionality using K-selectride was also optimized.

δ-Galactonolactone: Synthesis, isolation, and comparative structure and stability analysis of an elusive sugar derivative

Bierenstiel, Matthias,Schlaf, Marcel

, p. 1474 - 1481 (2007/10/03)

δ-D-Gluconolactone, δ-D-mannonolactone, and - for the first time - the thermodynamically unstable δ-D-galactonolactone have been prepared and isolated from DMF solution by oxidizing the corresponding sugars with Shvo's catalyst [(C4Ph4CO)(CO)2Ru] 2 and a hydrogen acceptor. The preferred conformation of δ-D-galactonolactone in [D6] DMSO solution has been determined by 1H NMR spectroscopy experiments and DFT calculations to be 4H3 and is compared to those of the previously established conformations of δ-D-gluconolactone (4H3) and δ-D-mannonolactone (B2,5), The conformations of the lactones suggest an explanation for their relative rates of isomerization to their respective γ-D-lactones by an intramolecular mechanism. Wiley-VCH Verlag GmbH & Co, KGaA, 69451 Weinheim, Germany, 2004.

A new efficient access to glycono-1,4-lactones by oxidation of unprotected itols by catalytic hydrogen transfer with RhH(PPh3)4-benzalacetone system

Isaac,Aizel,Stasik,Wadouachi,Beaupère

, p. 475 - 476 (2007/10/03)

Treatment of unprotected pentitols and hexitols with RhH(PPh3)4-benzalacetone system leads exclusively to glycono-1,4-lactones in 60-96% yield.

A NEW AND DIRECT ACCESS TO GLYCONO-1,4-LACTONES FROM GLYCOPYRANOSES BY REGIOSELECTIVE OXIDATION AND SUBSEQUENT RING RESTRICTION

Isaac, Isabelle,Stasik, Imane,Beaupere, Daniel,Uzan, Raoul

, p. 383 - 386 (2007/10/02)

Treatment of partially protected or unprotected carbohydrates with the RhH(PPh3)4-benzalacetone system leads exclusively to glycono-1,4-lactones by regioselective oxidation and subsequent ring restriction.

2-Acetamido-2-deoxyaldonolactones from sugar formazans

Zsoldos-Mady, Virag,Pinter, Istvan,Neszmelyi, Andras,Messmer, Andras,Perczel, Andras

, p. 85 - 96 (2007/10/02)

A new approach towards simple aldonic acid derivatives starting from the corresponding aldoses via the 2-acetamido-2-deoxy formazans resulted in the synthesis of 2-acetamido-2-deoxy-D-galactono-1,4-lactone (8), and its 6-deoxy (11) and 6-azido-6-deoxy (14) analogues on treatment with trifluoroacetic acid.The five-membered ring structure of the lactones and that of the intermediate lactone phenylhydrazone (7) was proved by 1H and 13C NMR studies, including deuterium-induced differential isotope shift (DIS) measurements.With sodium borohydride, lactones 8 and 11 were converted into 2-acetamido-2-deoxy-D-galactitol (15) and its 6-deoxy analogue (17), respectively.

Vitamin C and Isovitamin C Derived Chemistry. 2. Synthesis of Some Enantiomerically Pure 4,5,6-Trihydroxylated Norleucines

Vekemans, Jozef A. J. M.,Bruyn, Ronald G. M. de,Caris, Roberta C. H. M.,Kokx, Antonius J. P. M.,Konings, Jeroen J. H. G.,Godefroi, Erik F.

, p. 1093 - 1099 (2007/10/02)

A sequence leading to enantiomerically pure 4,5,6-trihydroxylated norleucines 23-25, their 5,6-O-isopropylidene derivatives 17a,b and 20, and lactones 19a,b and 22 from relatively inexpensive carbohydrate precursors is described. 5,6-O-Isopropylidene-L-gulono-, -D-mannono-, and -D-galactono-1,4-lactones (2a,b and 7b) react readily with 2 equiv of mesyl chloride in pyridine at 0 deg C to produce hex-2-enono-1,4-lactone 2-mesylates 5a,b and 8.The butenolides are stereoselectively reduced to 3-deoxyhexono-1,4-lactone 2-mesylates 11a,b and 12, which are then treated with sodium azide in DMF to generate the configurationally C-2-inverted azides 15a,b and 16.Hydrogenation thereof, in the presence of triethylamine, gives the 5,6-O-isopropylidenated title compounds 17a,b and 20, which are hydrolyzed in boiling water to give amino acids 23-25 and are converted into lactones 19a,b and 22 by treatment with dilute hydrochloric acid under reflux.The lactones are optimally produced directly from 15a,b and 16 by hydrogenation in the presence of acid.

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