22331-81-3Relevant academic research and scientific papers
3-Hydroxymuscarines from L-rhamnose
Mantell,Ford,Watkin,Fleet,Brown
, p. 3343 - 3358 (1993)
No protection is necessary for the synthesis of the muscarine analogue 3R-3-hydroxymuscarine from L-rhamnose; a sole silyl ether protecting group is required for the wsynthesis of 3S-3-hydroxymuscarine. Efficient construction of the tetrahydrofuran ring c
Functionalised tetrahydrofuran fragments from carbohydrates or sugar beet pulp biomass
Benhamou, Laure,Foster, Robert W.,Ward, David P.,Wheelhouse, Katherine,Sloan, Lisa,Tame, Christopher J.,Bu?ar, Dejan-Kre?imir,Lye, Gary J.,Hailes, Helen C.,Sheppard, Tom D.
supporting information, p. 2035 - 2042 (2019/04/29)
Carbohydrate biomass represents a potentially valuable sustainable source of raw materials for chemical synthesis, but for many applications, selective deoxygenation/dehydration of the sugars present is necessary to access compounds with useful chemical and physical properties. Selective dehydration of pentose sugars to give tetrahydrofurans can be achieved by treatment of the corresponding N,N-dimethylhydrazones under acidic or basic conditions, with the two approaches showing complementary stereoselectivity. The dehydration process is readily scalable and the THF hydrazones derived from arabinose, ribose, xylose and rhamnose were converted into a range of useful fragments containing primary alcohol, ketone, carboxylic acid or amine functional groups. These compounds have potentially useful physiochemical properties making them suitable for incorporation into fragment/lead generation libraries for medicinal chemistry. It was also shown that l-arabinose hydrazone could be obtained selectively from a crude sample of hydrolysed sugar beet pulp.
Sustainable Synthesis of Chiral Tetrahydrofurans through the Selective Dehydration of Pentoses
Foster, Robert W.,Tame, Christopher J.,Bu?ar, Dejan-Kre?imir,Hailes, Helen C.,Sheppard, Tom D.
supporting information, p. 15947 - 15950 (2015/11/03)
L-Arabinose is an abundant resource available as a waste product of the sugar beet industry. Through use of a hydrazone-based strategy, L-arabinose was selectively dehydrated to form a chiral tetrahydrofuran on a multi-gram scale without the need for protecting groups. This approach was extended to other biomass-derived reducing sugars and the mechanism of the key cyclization investigated. This methodology was applied to the synthesis of a range of functionalized chiral tetrahydrofurans, as well as a formal synthesis of 3R-3-hydroxymuscarine.
3R-hydroxymuscarine from L-rhamnose without protection
Mantell,Ford,Watkin,Fleet,Brown
, p. 4503 - 4506 (2007/10/02)
The synthesis of the muscarine analogue 3R-3-hydroxymuscarine [(2S,3R,4R,5S)-3,4-dihydroxytetrahydro-N,N,N,5-tetramethyl-2-furanmeth animium tosylate] from L-rhamnose does not require the use of any protecting group.
ANHYDROALDITOLS IN THE SUGAR ANALYSIS OF METHANOLYSATES OF ALDITOLS AND OLIGOSACCHARIDE-ALDITOLS
Gerwig, Gerrit J.,Kamerling, Johannis P.,Vliegenthart, Johannes F.G.
, p. 149 - 158 (2007/10/02)
In the context of the methanolysis procedure for sugar analysis, several alditols were investigated for their capacity to form anhydro derivatives in M methanolic HCl (24h, 85 deg C).Xylitol, D-arabinitol, L-fucitol, D-glucitol, galacticol, 2-acetamido-2-deoxy-D-galactitol, and the alditols of N-acetylneuraminic acid were very prone to form anhydrides, whereas 2-amino-2-deoxy-D-galactitol, 2-amino-deoxy-D-glucitol, D-mannitol, and 2-acetamido-2-deoxy-D-glucitol formed little anhydride.Anhydride formation was observed for the relevant alditols when present in reduced oligosaccharides.This findings is importance in the quantification of sugar residues based on methanolysis, N-(re)acetylation, trimethylsilylation, and subsequent capillary g.l.c.
