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T44407

Sigma-Aldrich

Tri-O-acetyl-D-glucal

98%

Synonym(s):

1,2-Dideoxy-3,4,6-tri-O-acetyl-D-arabino-1-hexenopyranose, 3,4,6-Tri-O-acetyl-1,5-anhydro-2-deoxy-D-arabino-hex-1-enitol

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About This Item

Empirical Formula (Hill Notation):
C12H16O7
CAS Number:
2873-29-2
Molecular Weight:
272.25
Beilstein:
90781
EC Number:
220-709-0
MDL number:
MFCD00063253
UNSPSC Code:
12352201
PubChem Substance ID:
24900208
NACRES:
NA.22

Quality Level

200

Assay

98%

form

crystalline powder

optical activity

[α]25/D −12°, c = 2 in ethanol

mp

53-55 °C (lit.)

SMILES string

CC(=O)OC[C@H]1OC=C[C@@H](OC(C)=O)[C@@H]1OC(C)=O

InChI

1S/C12H16O7/c1-7(13)17-6-11-12(19-9(3)15)10(4-5-16-11)18-8(2)14/h4-5,10-12H,6H2,1-3H3/t10-,11-,12+/m1/s1

InChI key

LLPWGHLVUPBSLP-UTUOFQBUSA-N

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Application

Important building block for both solution- and solid-phase synthesis of oligosaccharides.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Russell S Dahl et al.
Journal of the American Chemical Society, 126(27), 8356-8357 (2004-07-09)
This contribution describes the results of a new research effort in our laboratory aimed at the synthesis of novel aminoglycosides and amino-C-glycosides. Despite the importance of such compounds, and the previous development of some methodological solutions, this remains an important
Andreas H Franz et al.
The Journal of organic chemistry, 67(22), 7662-7669 (2002-10-26)
Lewis acid-catalyzed dimerization of mono- and disaccharidic per-O-acetylated glycals gave di- and tetrasaccharidic O-acetylated C-glycosides, respectively. 2,3-Enopyranosyl cyanides were obtained from per-O-acetylated glycals by a new, mild anomeric S(N)'-acetoxy displacement with Hg(CN)(2)/HgBr(2)/TMSCN. Per-O-acetylated 2-C-2-deoxy-pyranoses were converted into pyranosyl cyanides by
Oleksandr S Kanishchev et al.
Nucleosides, nucleotides & nucleic acids, 30(10), 768-783 (2011-10-05)
This paper offers the results of a synthesis and study of cytotoxicity and the anti-Epstein-Barr virus (EBV) activity of new 2-deoxy-2-chloro-pyranosyl derivatives of 4-tosyl-5-trifluoromethyl-1,2,3-triazole obtained via the addition reaction of the corresponding 2-N-chlorotriazole to the double bond of 3,4,6-tri-O-acetyl-D-glucal. Nucleoside
Clayton H Heathcock et al.
Journal of the American Chemical Society, 125(42), 12844-12849 (2003-10-16)
A multigram synthesis of the C29-C51 subunit of altohyrtin C (spongistatin 2) has been accomplished. Union of this intermediate with the C1-C28 fragment and further elaboration furnished the natural product. Completion of the C29-C51 subunit began with the aldol coupling
Application of molecular-mechanics calculations to D-glucal and its acetate; a comparison of X-ray and n.m.r. results.
W Korytnyk et al.
Carbohydrate research, 131(1), 157-165 (1984-08-01)
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