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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.

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)

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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
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
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
J S Yadav et al.
Carbohydrate research, 332(2), 221-224 (2001-07-04)
The treatment of glycals with allyltrimethylsilane in the presence of lithium tetrafluoroborate in acetonitrile gave the corresponding allyl 2,3-unsaturated C-glycosylic compounds in excellent yields with high anomeric selectivity.
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