Synthesis and reactions of chlorodeoxy-l-talofuranoid derivatives

Lee, Cheang-Kuan

doi:10.1016/0008-6215(90)80140-x

Cited by 10 publications

(3 citation statements)

References 9 publications

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“…After C5 epimerization this leads to l -idose − or l -gulose, , respectively. For instance, acetate-mediated double substitution of 5,6-di- O -sulfonyl d -gluco or d -manno-furanosides 40 and 45 leads, after deprotection of 41 and 45 , to the corresponding l -ido-pyranoside and l -gulo-furanosides 42 and 46 (Scheme a and b). , Further elaboration of the l -idofuranosides into other l -sugars, like l -talose and l -gulose, have also been reported. ,, In a similar approach l -talose was prepared from d -allofuranoside derivative. , The d -allofuranoside derivative was available from d -glucose.…”

Section: Synthesis Of L-aldohexoses From Carbohydratesmentioning

confidence: 79%

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Synthesis of l-Hexoses

2015

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Section: Synthesis Of L-aldohexoses From Carbohydratesmentioning

confidence: 79%

“…106,111 Further elaboration of the L-idofuranosides into other L-sugars, like L-talose and L-gulose, have also been reported. 108,113,114 In a similar approach L-talose was prepared from D-allofuranoside derivative. 115,116 The D-allofuranoside derivative was available from D-glucose.…”

Section: C5 Epimerizationsmentioning

confidence: 99%

Synthesis of l-Hexoses

2015

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“…After the initial formation of the six‐membered cyclic oxocarbenium species ( 42 ), an intramolecular rearrangement occurs, where the vicinal ester moiety opens the oxocarbenium ion, with the formation of a dioxolonium ion ( 43 ). This ion is then opened through a nucleophilic attack by a bromide ion (Scheme ) …”

Section: Furansmentioning

confidence: 99%

Regioselective Ring Opening of 1,3‐Dioxane‐Type Acetals in Carbohydrates

et al. 2018

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The (regio)selective manipulation of hydroxyl groups in carbohydrates has been a long‐standing challenge in (bio)organic chemistry and continues to trigger the creative minds of many chemists. Among the various strategies that have been developed to address these issues, mostly relying on multistep procedures involving the use of protecting groups, the regioselective ring opening of 1,3‐dioxane‐type acetals has emerged as a powerful tool. Since the first papers on this subject appeared in the 1960s, a large variety in both acetal types and reagents for their partial cleavage has come to the fore. This review aims to give an overview of the different carbohydrate‐derived ring systems, ranging from four‐ to seven‐membered rings, on which regioselective ring‐openings have been performed, along with the appropriate reagents and combinations thereof. The transformations on 1,3‐dioxane acetals fit in a larger group of ring opening reactions of structurally related cyclic functional groups, including 1,3‐dioxolanes, 1,3‐oxathianes, orthoesters, cyclic carbonates and silylene acetals, which will not be discussed in this review.

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Collins¹

1998

Dictionary of Carbohydrates

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Synthesis and reactions of chlorodeoxy-l-talofuranoid derivatives

Cited by 10 publications

References 9 publications

Synthesis of l-Hexoses

Synthesis of l-Hexoses

Regioselective Ring Opening of 1,3‐Dioxane‐Type Acetals in Carbohydrates

B

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