1,6-Anhydro-2,3-dideoxy-b-D-threo-hex-2-enopyranose - CAS 58394-32-4
Category:
Carbohydrates
Product Name:
1,6-Anhydro-2,3-dideoxy-b-D-threo-hex-2-enopyranose
CAS Number:
58394-32-4
Related CAS:
52630-81-6
Molecular Weight:
128.13
Molecular Formula:
C6H8O3
COA:
Inquire
MSDS:
Inquire
Structure:
Monosaccharides
Chemical Structure
CAS 58394-32-4 1,6-Anhydro-2,3-dideoxy-b-D-threo-hex-2-enopyranose

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Reference Reading


1.Synthesis of all configurational isomers of 1,6-anhydro-2,3,4-trideoxy-2,3-epimino-4-fluoro-beta-d-hexopyranoses.
Karban J1, Sýkora J, Kroutil J, Císarová I, Padelková Z, Budesínský M. J Org Chem. 2010 May 21;75(10):3443-6. doi: 10.1021/jo1000912.
We have prepared a full series of 1,6-anhydro-2,3,4-trideoxy-4-fluoro-2,3-epimino-beta-d-hexopyranoses. The key step was the reaction of azido sulfonates possessing a free C-4 hydroxyl with DAST and subsequent LiAlH(4) reduction. Nucleophilic displacement of the hydroxyl activated by DAST proceeded without rearrangement and with moderate to good yields. A convenient synthesis of d-mannoepimine from a readily available 3-benzylamino derivative was also developed.
2.Galactans from Cryptonemia species. Part II: studies on the system of galactans of Cryptonemia seminervis (Halymeniales) and on the structure of major fractions.
Zibetti RG1, Duarte ME, Noseda MD, Colodi FG, Ducatti DR, Ferreira LG, Cardoso MA, Cerezo AS. Carbohydr Res. 2009 Nov 23;344(17):2364-74. doi: 10.1016/j.carres.2009.09.003. Epub 2009 Sep 6.
Cryptonemia seminervis biosynthesizes a family of D,L-hybrid galactans based on the classical 3-linked beta-D-galactopyranosyl-->4-linked alpha-D- and alpha-L-galactopyranosyl alternating sequence (A-units-->B-units) with major amounts of alpha-D- and alpha-L-galactose and 3,6-anhydro-D- and L-galactose and lesser percentages of 3,6-anhydro-2-O-methyl-L-galactose, 2-O-methyl-, 4-O-methyl- and 6-O-methylgalactoses. The dispersion of structures in this family is based on five structural factors, namely: (a) the amount and position of substituent groups as sulfate (major), pyruvic acid ketals, methoxyl and glycosyl side-chain (4-O-methyl galactopyranosyl and/or xylosyl); (b) the ratio galactose/3,6-anhydrogalactose in the B-units; (c) the ratio D,L-galactoses and D,L-3,6-anhydrogalactoses also in the B-units, (d) the formation of diads and (e) the sequence of the diads in the linear backbone. Considering these variables it is not unexpected to find in the fractions studied at least 18 structural units producing highly complex structures.
3.Synthesis, characterization and reactivity of carbohydrate platinum(IV) complexes with thioglycoside ligands.
Vetter C1, Pornsuriyasak P, Schmidt J, Rath NP, Rüffer T, Demchenko AV, Steinborn D. Dalton Trans. 2010 Jul 21;39(27):6327-38. doi: 10.1039/b927058b. Epub 2010 Jun 1.
Reactions of fac-[PtMe3(4,4'-R2bpy)(Me2CO)][BF4] (R = H, 1a; tBu, 1b) and fac-[PtMe3(OAc-kappa2O,O')(Me2CO)] (2), respectively, with thioglycosides containing thioethyl (ch-SEt) and thioimidate (ch-STaz, Taz = thiazoline-2-yl) anomeric groups led to the formation of the carbohydrate platinum(IV) complexes fac-[PtMe3(4,4-R2bpy)(ch*)][BF4] (ch* = ch-SEt, 8-14; ch-STaz, 15-23) and fac-[PtMe3(OAc-kappa2O,O')(ch*)] (ch* = ch-SEt, 24-28; ch-STaz = 29-35), respectively. NMR (1H, 13C, 195Pt) spectroscopic investigations and a single-crystal X-ray diffraction analysis of 19 (ch-STaz = 2-thiazolinyl 2,3,4,6-tetra-O-benzoyl-1-thio-beta-D-galactopyranose) revealed the S coordination of the ch-SEt glycosides and the N coordination of the ch-STaz glycosides. Furthermore, X-ray structure analyses of the two decomposition products fac-[PtMe3(bpy)(STazH-kappaS)][BF4] (21a) and 1,6-anhydro-2,3,4-tri-O-benzoyl-beta-D-glucopyranose (23a), where a cleavage of the anomeric C-S bond had occurred in both cases, gave rise to the assumption that this decomposition was mediated due to coordination of the thioglycosides to the high electrophilic platinum(IV) atom, in non-strictly dried solutions.
4.Thermal decomposition of beta-D-galactopyranosyl-(1-->3)-2-acetamido-2-deoxy-D-hexopyranoses under neutral conditions.
Chiku K1, Nishimoto M, Kitaoka M. Carbohydr Res. 2010 Sep 3;345(13):1901-8. doi: 10.1016/j.carres.2010.06.003. Epub 2010 Jun 15.
beta-d-Galactopyranosyl-(1-->3)-2-acetamido-2-deoxy-d-glucose (LNB) and beta-d-galactopyranosyl-(1-->3)-2-acetamido-2-deoxy-d-galactose (GNB) decompose rapidly upon heating into d-galactose and mono-dehydrated derivatives of the corresponding 2-acetamido-2-deoxy-d-hexoses, including 2-acetamido-2,3-dideoxy-hex-2-enofuranoses and bicyclic 2-acetamido-3,6-anhydro-2-deoxy-hexofuranoses. The decomposition is conducted under neutral conditions where glycosyl linkages are generally believed to be stable. The half-lives of LNB and GNB were 8.1min and 20min, respectively, at 90 degrees C and pH 7.5. The pH dependency of decomposition rates suggests that the instabilities are an extension of the conditions for the peeling reaction, often observed with glycans of O-linked glycoproteins under alkaline conditions. Such decomposition under the neutral conditions is commonly observed with 3-O-linked reducing aldoses.