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Topic

Glucal

About: Glucal is a(n) research topic. Over the lifetime, 590 publication(s) have been published within this topic receiving 8960 citation(s). The topic is also known as: D-glucal.


Papers
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Journal ArticleDOI
TL;DR: Nojirimycin can be used to differentiate between α-glucosidase and exo-α- d -glucanase, and between β-gloucono-1,5-lactone and ex-β- β-d -glugal, and the structural similarity of the two inhibitors is discussed.
Abstract: Nojirimycin and d -glucono-1,5-lactone are powerful inhibitors of glucosidases, but poor inhibitors of exo-glucanases, endo-glucanases, and related enzymes. Nojirimycin can be used to differentiate between α-glucosidase and exo-α- d -glucanase, and between β-glucosidase and exo-β- d -glucanase. The structural similarity of the two inhibitors is discussed in relation to the mechanism of action of the enzyme types. Some data on d -glucal are included.

185 citations

Journal ArticleDOI
Abstract: Tri-O-acetyl-D-glucal undergoes complete reaction with alcohols in benzene solution in the presence of boron trifluoride to give 4,6-di-O-acetyl-2,3-dideoxy-D-erythro-hex-2-enopyranosides. The α-anomers predominate (ca. 90%), and the method can be used to prepare the known crystalline ethyl α-glucoside easily and in greatly improved yield. Other alkyl glycosides have been prepared similarly, and the procedure has afforded means of obtaining the cholesteryl analogue and the disaccharide derivative 6-O-(4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose. Tri-O-acetyl-D-glucal again gave the 2,3-unsaturated glycosides on treatment with acetals in the presence of boron trifluoride; no evidence was obtained for the formation of branched-chain products produced by additions to the double bond.

175 citations

Journal ArticleDOI
TL;DR: The first total synthesis of a major component of the microbial biosurfactant sophorolipid has been achieved using a ring-closing metathesis reaction of diyne 21 catalyzed by Mo[N(t-Bu)(Ar)](3) (5; Ar = 3,5-dimethylphenyl) activated in situ by CH(2)Cl(2), followed by Lindlar reduction of the resulting cycloalkyne 22.
Abstract: The first total synthesis of a major component of the microbial biosurfactant sophorolipid has been achieved This approach to the 26-membered macrolide 1 containing a Z-configured alkene group in its lipidic tether spanning the sophorose backbone is based on a ring-closing metathesis reaction of diyne 21 catalyzed by Mo[N(t-Bu)(Ar)]3 (5; Ar = 3,5-dimethylphenyl) activated in situ by CH2Cl2, followed by Lindlar reduction of the resulting cycloalkyne 22 The two β-glycosidic linkages of compound 21 were installed by means of the glucal epoxide method and a modified Koenigs−Knorr reaction promoted by AgOTf/lutidine, respectively

122 citations

Journal ArticleDOI
TL;DR: Perchloric acid supported on silica gel acts as an excellent reagent system in converting glucals into 2,3-unsaturated-O-glucosides in good to excellent yields in short reaction time with good alpha selectivity.
Abstract: Perchloric acid supported on silica gel acts as an excellent reagent system in converting glucals into 2,3-unsaturated-O-glucosides in good to excellent yields in short reaction time with good a selectivity. Primary, secondary, and allylic alcohols, phenols, and thiols react with 3,4,6-tri-O-acetyl glucal with equal ease. In addition to this, a chiral furan diol is obtained from unprotected D-glucal or D-galactal in good yields.

109 citations

Journal ArticleDOI
Abstract: In the presence of mercuric sulfate, 3,4,6-tri- O -acetyl- d -glucal ( 4 ), dissolved in 1,4-dioxane-dilute sulfuric acid at room temperature, is rapidly and quantitatively converted into 4,6-di- O -acetyl-2,3-dideoxy- aldelhydo d - erythro - trans -hex-2-enose ( 8 ). With acetone as the organic component of the solvent, this product is accompanied by the 5,6-di- O -acetyl isomer ( 10 ). The corresponding, α,β-unsaturated aldehydes ( 12 and 13 ; 15 ) are formed in an analogous way from 3,4,6-tri- O -acetyl- d -galactal ( 11 ) and 3,4-di- O -acetyl- d -arabinal ( 14 ). Similarly, instead of hydration, d -glucal ( 1 ) and d -galactal undergo elimination catalyzed by mercuric ion and acid to yield 2-( d - glycero -1,2-dihydroxyethyl)furan ( 3 ) as the sole product. Possible mechanisms for these transformations are discussed.

102 citations

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Performance
Metrics
No. of papers in the topic in previous years
YearPapers
20212
20204
20193
20186
20179
201611