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Glucal

About: Glucal is a research topic. Over the lifetime, 590 publications have been published within this topic receiving 8960 citations. The topic is also known as: D-glucal.


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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.

189 citations

Journal ArticleDOI
TL;DR: Tri-O-acetyl-D-glucal undergoes complete reaction with alcohols in benzene solution in the presence of boron trifluoride to give 4,6-di-OðOðAðEðDÞÞ −2,3-dideoxy-α-DÒÞ−EðE Þ−hex-hex-2-enopyranosyl as discussed by the authors, which can be used to prepare the known crystalline ethyl αglucoside easily and in greatly improved
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.

179 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

123 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.

113 citations

Journal ArticleDOI
TL;DR: 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

103 citations


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Performance
Metrics
No. of papers in the topic in previous years
YearPapers
20233
20224
20212
20204
20193
20186