Synthesis of some aryl 2,3,4,6-tetra-O-acetyl-l-idopyranosides and of 4-methylcoumarin-7-yl α-l-idopyranosiduronic acid

Baggett, N.; Samra, Amarjit K.; Smithson, Alan

doi:10.1016/0008-6215(83)88356-6

Cited by 15 publications

(2 citation statements)

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“…4 One well-known technique used for the diagnosis of all clinical types of MPS I is the measurement of IDUA activity, 5 wherein 4-methylcoumarin-7-yl-α-L-iduronic acid (4) is used as fluorogenic substrate. 6 However, this particular substrate is very expensive (>US$100 per mg)…”

Section: Introductionmentioning

confidence: 99%

“…7 Although several synthetic approaches have been reported on the synthesis of L-ido sugars and their coumarin derivatives, the strategy still involves tedious steps and remains low yielding at the glycosylation stage. 6,8 Thus, we explored and developed alternative methods of preparing L-ido sugars, 8c,d,9 such as compound 3, from different D-glucose derivatives and used these materials as key intermediates for the synthesis of the fluorogenic substrate 4. Scheme 1.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of a fluorogenic substrate for α-L-iduronidase

Lu¹,

Lico²,

Hung³

2012

Arkivoc

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An alternative reaction pathway towards the preparation of an L-idopyranose derivative and its application to the synthesis of the α-L-iduronidase fluorogenic substrate 4-methylcoumarin-7-yl-α-L-iduronic acid as well as its 3-undecyl derivative are described. The L-ido sugar was prepared by converting the commercially available diacetone-α-D-glucose to methyl 1,2,3,4-tetra-Oacetyl-L-idopyranuronate via oxidation, esterification, and regioselective acetylation of the key intermediate 1,2:3,5-di-O-isopropylidene-β-L-idofuranose. Mitsunobu-type glycosylation was employed in the coupling of the L-ido donor with the 4-methylcoumarin acceptors. This newly developed route reduced the difficulties previously encountered in the synthesis of the α-Liduronidase fluorogenic substrate.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis of a fluorogenic substrate for α-L-iduronidase

Lu¹,

Lico²,

Hung³

2012

Arkivoc

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From D‐Glucose to Biologically Potent L‐Hexose Derivatives: Synthesis of α‐L‐Iduronidase Fluorogenic Detector and the Disaccharide Moieties of Bleomycin A₂ and Heparan Sulfate

Lee

Chang

Liao

et al. 2004

Chemistry A European J

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A novel and convenient route for the synthesis of biologically potent and rare L-hexose derivatives from D-glucose is described. Conversion of diacetone-alpha-D-glucose (14) into 1,2:3,5-di-O-isopropylidene-beta-L-idofuranose (19) was efficiently carried out in two steps. Orthogonal isopropylidene rearrangement of compound 19 led to 1,2:5,6-di-O-isopropylidene-beta-L-idofuranose (27), which underwent regioselective epimerization at the C3 position to give the L-talo- and 3-functionalized L-idofuranosyl derivatives. Hydrolysis of compound 19 under acidic conditions furnished 1,6-anhydro-beta-L-idopyranose (35) in excellent yield, which was successfully transformed into the corresponding L-allo, L-altro, L-gulo, and L-ido derivatives via regioselective benzylation, benzoylation, triflation and nucleophilic substitution as the key steps. Applications of these 1,6-anhydro-beta-L-hexopyranoses as valuable building blocks to the syntheses of 4-methylcoumarin-7-yl-alpha-L-iduronic acid and the disaccharide moieties of bleomycin A(2) as well as heparan sulfate are highlighted.

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ChemInform Abstract: SYNTHESIS OF SOME ARYL 2,3,4,6‐TETRA‐O‐ACETYL‐L‐IDOPYRANOSIDES AND OF 4‐METHYLCOUMARIN‐7‐YL α‐L‐IDOPYRANOSIDURONIC ACID

Baggett¹,

Samra²,

Smithson³

1984

Chemischer Informationsdienst

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Synthesis of some aryl 2,3,4,6-tetra-O-acetyl-l-idopyranosides and of 4-methylcoumarin-7-yl α-l-idopyranosiduronic acid

Cited by 15 publications

References 29 publications

Synthesis of a fluorogenic substrate for α-L-iduronidase

Synthesis of a fluorogenic substrate for α-L-iduronidase

From D‐Glucose to Biologically Potent L‐Hexose Derivatives: Synthesis of α‐L‐Iduronidase Fluorogenic Detector and the Disaccharide Moieties of Bleomycin A₂ and Heparan Sulfate

ChemInform Abstract: SYNTHESIS OF SOME ARYL 2,3,4,6‐TETRA‐O‐ACETYL‐L‐IDOPYRANOSIDES AND OF 4‐METHYLCOUMARIN‐7‐YL α‐L‐IDOPYRANOSIDURONIC ACID

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Synthesis of some aryl 2,3,4,6-tetra-O-acetyl-l-idopyranosides and of 4-methylcoumarin-7-yl α-l-idopyranosiduronic acid

Cited by 15 publications

References 29 publications

Synthesis of a fluorogenic substrate for α-L-iduronidase

Synthesis of a fluorogenic substrate for α-L-iduronidase

From D‐Glucose to Biologically Potent L‐Hexose Derivatives: Synthesis of α‐L‐Iduronidase Fluorogenic Detector and the Disaccharide Moieties of Bleomycin A2 and Heparan Sulfate

ChemInform Abstract: SYNTHESIS OF SOME ARYL 2,3,4,6‐TETRA‐O‐ACETYL‐L‐IDOPYRANOSIDES AND OF 4‐METHYLCOUMARIN‐7‐YL α‐L‐IDOPYRANOSIDURONIC ACID

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From D‐Glucose to Biologically Potent L‐Hexose Derivatives: Synthesis of α‐L‐Iduronidase Fluorogenic Detector and the Disaccharide Moieties of Bleomycin A₂ and Heparan Sulfate