1,2,3,4,6-Penta-O-acetyl-D-mannopyranose - CAS 25941-03-1
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D-Mannose pentaacetate
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CAS 25941-03-1 1,2,3,4,6-Penta-O-acetyl-D-mannopyranose

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1.[Automated synthesis of 2-[(18)F]-fluoro-2-deoxy-D-glucose by on-column hydrolysis].
Luo L1, Tang G, Tang X. Zhong Nan Da Xue Xue Bao Yi Xue Ban. 2009 Nov;34(11):1151-6.
OBJECTIVE: To study automated synthesis of 2-[(18)F]-fluoro-2-deoxy-D-glucose ((18)F-FDG) via on-column hydrolysis.
2.3,4,6-Tri-O-acetyl-1,2-O-[1-(exo-ethoxy)ethylidene]-β-D-mannopyranose 0.11-hydrate.
Liu YL1, Zou P, Wu H, Xie MH, Luo SN. Acta Crystallogr C. 2012 Sep;68(Pt 9):o338-40. doi: 10.1107/S0108270112032076. Epub 2012 Aug 1.
The title compound, C(16)H(24)O(10)·0.11H(2)O, is a key intermediate in the synthesis of 2-deoxy-2-[(18)F]fluoro-D-glucose ((18)F-FDG), which is the most widely used molecular-imaging probe for positron emission tomography (PET). The crystal structure has two independent molecules (A and B) in the asymmetric unit, with closely comparable geometries. The pyranose ring adopts a (4)C(1) conformation [Cremer-Pople puckering parameters: Q = 0.553 (2) Å, θ = 16.2 (2)° and φ = 290.4 (8)° for molecule A, and Q = 0.529 (2) Å, θ =15.3 (3)° and φ = 268.2 (9)° for molecule B], and the dioxolane ring adopts an envelope conformation. The chiral centre in the dioxolane ring, introduced during the synthesis of the compound, has an R configuration, with the ethoxy group exo to the mannopyranose ring. The asymmetric unit also contains one water molecule with a refined site-occupancy factor of 0.222 (8), which bridges between molecules A and B via O-H···O hydrogen bonds.
3.Practical preparation of 2-azido-2-deoxy-beta-D-mannopyranosyl carbonates and their application in the synthesis of oligosaccharides.
Zhang J1, Yan S, Liang X, Wu J, Wang D, Kong F. Carbohydr Res. 2007 Dec 28;342(18):2810-7. Epub 2007 Sep 7.
1-O-Allyloxycarbonyl (or ethyloxycarbonyl)-2-azido-2-deoxy-3-O-benzyl (or allyl, or benzoyl)-4,6-O-isopropylidene-beta-d-mannopyranose derivatives were prepared from the corresponding 2-hydroxy-beta-d-glucopyranosyl carbonates in high yields via triflation of the 2-hydroxyl group and subsequent SN2 displacement with azide ion. An N-acetyl-mannosamine-containing trisaccharide, a fragment of the putative O10 antigen from Acinetobacter baumannii, was efficiently synthesized using these derivatives.
4.Polymerization of mannosyl tricyclic orthoesters for the synthesis of alpha(1-6) mannopyranan-the backbone of lipomannan.
Yongyat C1, Ruchirawat S, Boonyarattanakalin S. Bioorg Med Chem. 2010 Jun 1;18(11):3726-34. doi: 10.1016/j.bmc.2010.04.014. Epub 2010 Apr 18.
Tuberculosis (TB) remains a major health problem worldwide. Understanding the interactions between the surface components of Mycobacterium tuberculosis (Mtb), the main causative agent of TB, with host immune response will be critical for developments of effective treatments and prevention of TB. Chemically defined mimics of the bacterial envelope components serve as important tools for biological studies of the bacterial interactions with mammalian hosts. We report here a rapid synthetic approach utilizing mannosyl tricyclic orthoesters as monomers for regio- and stereo-controlled polymerizations to generate alpha(1-6) mannopyranan-the backbone of lipomannan. The polymerizations generated multiple glycosidic bonds in a single chemical transformation in regio- and stereo-selective manners. TMSOTf is the optimum catalyst to promote the selective and high yielding polymerization when compared with other Lewis acids. In addition, the monomers 3,4-O-benzyl-beta-d-mannopyranose 1,2,6-orthobenzoate (1) and 3,4-O-benzyl-beta-d-mannopyranose 1,2,6-orthopivalate (2) can be synthesized in multiple-gram scale and in a rapid fashion.