Selective deacetylation of anomeric sugar acetates with tin alkoxides

Nudelman, Abraham; Herzig, J.; Gottlieb, Hugo E.; Keinan, Ehud; Sterling, Jeffrey

doi:10.1016/0008-6215(87)80209-4

Cited by 81 publications

(39 citation statements)

References 45 publications

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“…By applying the reported procedure, 5) a-glucuronate 15 and b-glucuronate 16 were independently treated with tributyltin methoxide (Bu 3 SnOMe) to provide the triacetyl-a-glucuronate 17 (60%), and (17) (99%), respectively. By applying the reported procedure, 6) the reaction of 17 with K 2 CO 3 in the presence of molecular sieves (MS, 3 Å), followed by treatment with trichloroacetonitrile (CCl 3 CN), provided the desired a-imidate 18 in 75%.…”

Section: Synthesis Of Glucuronide Imidate 18mentioning

confidence: 99%

Synthesis of Methyl 1-O-(4-Hydroxymethamphetaminyl)-.ALPHA.-D-glucopyranouronate

Nakajima

Ono

Aiso

et al. 2005

CHEMICAL & PHARMACEUTICAL BULLETIN

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Section: Synthesis Of Glucuronide Imidate 18mentioning

confidence: 99%

Synthesis of Methyl 1-O-(4-Hydroxymethamphetaminyl)-.ALPHA.-D-glucopyranouronate

Nakajima

Ono

Aiso

et al. 2005

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…It has also seen utility for access to and characterization of the important glucuronide-containing metabolite 5 (Scheme 2, C). 5 Importantly, 2 also serves as a vital precursor for the formation of alternative C-1 anomeric derivatives 4 (complicit to wider glycosylation applications and methodologies) including trichloroacetimidates, 5 hemi-acetals, 6 and glycosyl bromides 7 (Scheme 2, B). …”

Section: Discussionmentioning

confidence: 99%

Preparation of Methyl 1,2,3,4‐tetra‐ O ‐acetyl‐β‐ D ‐glucopyranuronate

et al. 2017

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This article describes the synthesis of methyl 1,2,3,4‐tetra‐ O ‐acetyl‐ β ‐D‐glucopyranuronate. it has been used to access non‐readily available L‐IdoA units for the construction of complex heparin‐related disaccharides, via an intermediate C5‐bromide. It has also seen utility for access to and characterization of the important glucuronide‐containing metabolite. Importantly, it also serves as a vital precursor for the formation of alternative C‐1 anomeric derivatives.

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“…The anomeric acetates can also be reacted with different tinreagents to give 1-O-tin derivatives, which subsequently are hydrolyzed (Entries 5-7). [127][128][129] Bases, such as NaOMe, usually give global deacetylation of peracetylated sugars. However, 2…”

Section: Removal Of Anomeric Protective Groupsmentioning

confidence: 99%

Chemistry of xylopyranosides

Thorsheim

Siegbahn

Johnsson

et al. 2015

Carbohydrate Research

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Xylose is one of the few monosaccharidic building blocks that are used by mammalian cells. In comparison with other monosaccharides, xylose is rather unusual and, so far, only found in two different mammalian structures, i.e. in the Notch receptor and as the linker between protein and glycosaminoglycan (GAG) chains in proteoglycans. Interestingly, simple soluble xylopyranosides can not only initiate the biosynthesis of soluble GAG chains but also function as inhibitors of important enzymes in the biosynthesis of proteoglycans. Furthermore, xylose is a major constituent of hemicellulosic xylans and thus one of the most abundant carbohydrates on Earth. Altogether, this has spurred a strong interest in xylose chemistry. The scope of this review is to describe synthesis of xylopyranosyl donors, as well as protective group chemistry, modifications, and conformational analysis of xylose.

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Selective deacetylation of anomeric sugar acetates with tin alkoxides

Cited by 81 publications

References 45 publications

Synthesis of Methyl 1-O-(4-Hydroxymethamphetaminyl)-.ALPHA.-D-glucopyranouronate

Synthesis of Methyl 1-O-(4-Hydroxymethamphetaminyl)-.ALPHA.-D-glucopyranouronate

Preparation of Methyl 1,2,3,4‐tetra‐ O ‐acetyl‐β‐ D ‐glucopyranuronate

Chemistry of xylopyranosides

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