Synthesis of Disaccharides, Containing Sulfur in the Ring of the Reducing Monosaccharide Unit, Through a Nonglycosylating Chemical Strategy

Isac‐García, Joaquín; Calvo‐Flores, Francisco G.; Hernández-Matéo, Fernando; Santoyo‐González, Francisco

doi:10.1002/(sici)1521-3765(19990503)5:5<1512::aid-chem1512>3.0.co;2-a

Cited by 14 publications

(1 citation statement)

References 23 publications

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“…Keeping the retrosynthetic strategy in mind, we started the synthesis of 22 from the 1,6-anhydro disaccharide 17 , which was prepared from d -(+)-cellobiose (Scheme ). Compound 17 was prepared by simple acetonation of cellobiose under modified Isac-García conditions . After testing several different conditions to obtain the tri- O -isopropylidene dimethyl acetal, we observed that addition of dry SiO 2 to the reaction mixture significantly increases the yield.…”

Section: Results and Discussionmentioning

confidence: 99%

Application of the EF and GH Fragments to the Synthesis of Idraparinux

2017

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A novel total synthesis of fully protected idraparinux has been achieved. A short and efficient protocol for the synthesis of the EF fragment of idraparinux and its C5'-epi analogue (GH unit) has been developed. The same cellobiose unit was transformed in 14 steps into the fully protected EF and GH disaccharide fragments. The key step of this approach is an epimerization of C5 by an elimination-addition sequence leading to l-ido disaccharide (GH unit) with a total yield of 24% (36% for the EF fragment). 1,6-Anhydro ring opening gave suitable substrates for efficient synthesis of fully protected idraparinux. The fully protected antithrombotic pentasaccharide idraparinux was synthesized in 23 steps for the longest linear route, with a 1.7% overall yield from d-cellobiose and d-glucose.

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Section: Results and Discussionmentioning

confidence: 99%

Application of the EF and GH Fragments to the Synthesis of Idraparinux

2017

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Zemplén Deacetylation

2010

Comprehensive Organic Name Reactions and Reagents

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The efficient removal of the O ‐acetyl protecting groups of carbohydrates by treatment of the O ‐acetylated substrates in methanol with a catalytic amount of sodium methoxide at room temperature is generally known as the Zemplén deacetylation, Zemplén de‐ O ‐acetylation, or Zemplen deacetylation. In addition, after the reaction, the O ‐acetyl‐protected carbohydrates are transformed into unprotected ones, in a manner analogous to the hydrolysis of an ester, thus this reaction is termed as the Zemplen saponification as well. However, it has been reported that the Zemplén deacetylation is probably not suitable for the deprotection of carbohydrates with disulfide linkages. This reaction has wide applications in carbohydrate chemistry.

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Three‐Membered Heterocycles. Structure and Reactivity

Murphree

2011

Modern Heterocyclic Chemistry

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Synthesis of Disaccharides, Containing Sulfur in the Ring of the Reducing Monosaccharide Unit, Through a Nonglycosylating Chemical Strategy

Abstract: A novel ring‐opening–recyclisation approach of the nonreducing sugar residue is reported for the formation of thio sugars from vicinal diols of natural disaccharides (lactose, maltose and cellobiose; see scheme), via cyclic sulfates.

Cited by 14 publications

References 23 publications

Application of the EF and GH Fragments to the Synthesis of Idraparinux

Application of the EF and GH Fragments to the Synthesis of Idraparinux

Zemplén Deacetylation

Three‐Membered Heterocycles. Structure and Reactivity

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