Synthesis of D-glycopyranosyl azides from 1,2-anhydrosugars using lithium azidohydridodiisobutylaluminate

Lee, Goo Soo; Min, Hye Kyung; Chung, Bong Young

doi:10.1016/s0040-4039(98)02435-6

Cited by 11 publications

(2 citation statements)

References 4 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The epoxide opening was successively studied with different N-nucleophiles by Chung et al, 63 who reported the regio-and stereoselective azido attack on D-glucal-, D-galactal and D-allal-derived epoxides, 86 or 89, to provide the desired 1-azido-1-deoxyglycopyranosides. In particular, the addition of lithium azidohydridodiisobutylaluminate (DIBAH-LiN 3 ) to the 1,2-anhydrosugars in THF afforded the 1-azido derivatives in good yields.…”

Section: Aminohydroxylation Reaction: Synthesis Of 1-aminosugarsmentioning

confidence: 99%

From glycals to aminosugars: a challenging test for new stereoselective aminohydroxylation and related methodologies

2016

View full text Add to dashboard Cite

The introduction of amino functionalities in a regio- and stereoselective manner onto sugar scaffolds represents a great challenge in carbohydrate synthesis. The most relevant methods to access 1-, 2-, 3-amino or 1,2-diaminosugars starting from glycals and 2,3-hexenopyranosides derived from them are concisely reviewed. The main synthetic strategies for accessing this class of compounds are classified in intermolecular and intramolecular approaches and the key features of each class are discussed. This review highlights how carbohydrate derivatives always pose great challenges representing a benchmark for assessing the efficiency of stereoselective strategies, and aims to give the readers inspiration for the development of new procedures.

show abstract

Section: Aminohydroxylation Reaction: Synthesis Of 1-aminosugarsmentioning

confidence: 99%

From glycals to aminosugars: a challenging test for new stereoselective aminohydroxylation and related methodologies

2016

View full text Add to dashboard Cite

show abstract

“…d -Glucal derivative 1 (prepared from β- d -glucose pentaacetate in five steps and 47% overall yield) was transformed into β- C -glycoside 2 on a multigram scale in 66% yield by dimethyldioxirane (DMDO) oxidation and Cu I -mediated addition of ( i PrO)Me 2 SiCH 2 MgCl, followed by Tamao−Kumada oxidation (see Scheme 1). , The unsymmetrically protected C -glycoside 2 was converted in two steps to partially benzylated triol 3 , followed by TEMPO oxidation to carboxylic acid 4 and decarboxylative elimination to 3*,6*- O -dibenzyl- l -glucal 5 using N , N -dimethylformamide dineopentyl acetal (DMFDNA) . The latter procedure has been used previously to introduce Δ 4,5 -unsaturation into the pyranose ring of O -glycosides. , Overall, the conversion of d -glucal 1 to l -glucal 5 was accomplished in seven steps and 36% yield.…”

mentioning

confidence: 99%