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beta-D-Ribofuranose 1,2,3,5-tetraacetate

beta-D-Ribofuranose 1,2,3,5-tetraacetate ??? ???
?? ??:
13035-61-5
???:
beta-D-Ribofuranose 1,2,3,5-tetraacetate
???(??):
(2S,3R,4R,5R)-5-(acetoxymethyl)tetrahydrofuran-2,3,4-triyl triacetate;TETRAACETYLRIBOFURANOSE;beta-D-Ribofuranose;1,2,3,5-Tetraacetate;TETRA-O-ACETYL-BETA-D-RIBOFURANOSE;1,2,3,5-tera-O-acetyl-beta-D-ribofuranose;1,2,3,5-TETRA-O-ACETYL-BETA-D-RIBOFURANOSE;[(2R,3R,4R,5S)-3,4,5-triacetoxytetrahydrofuran-2-yl]methyl acetate;TETRAACETYLRIBOSE;RIBOFURANOSE TETRAACETATE
CBNumber:
CB4682585
???:
C13H18O9
??? ??:
318.28
MOL ??:
13035-61-5.mol

beta-D-Ribofuranose 1,2,3,5-tetraacetate ??

???
81-83 °C(lit.)
?? ?
417.45°C (rough estimate)
??
-15.4 º (c=7, MeOH)
??
1.4171 (rough estimate)
???
-14.5 ° (C=5, MeOH)
?? ??
Inert atmosphere,Room Temperature
???
?????(???? ??), ???(?? ???)
??? ??
??? ??
??
???? ?? ??
??? (Optical Rotation)
[α]26/D 11.4°, c = 10 in chloroform
BRN
94078
InChI
InChI=1/C13H18O9/c1-6(14)18-5-10-11(19-7(2)15)12(20-8(3)16)13(22-10)21-9(4)17/h10-13H,5H2,1-4H3/t10-,11-,12-,13-/s3
InChIKey
TTXVPMATRDJQIA-BKUVIOGVSA-N
SMILES
[C@@H]1(OC(=O)C)[C@@H](COC(=O)C)O[C@@H](OC(=O)C)[C@@H]1OC(=O)C |&1:0,5,12,17,r|
CAS ??????
13035-61-5(CAS DataBase Reference)
??
  • ?? ? ?? ??
  • ?? ? ???? ?? (GHS)
??? ?? Xi
?? ???? ?? 36/37/38
????? 22-24/25-36-26
WGK ?? 3
HS ?? 29400090
????(GHS): GHS hazard pictograms
?? ?: Warning
??·?? ??:
?? ??·?? ?? ?? ?? ?? ?? ? ?? ?? P- ??
H315 ??? ??? ??? ????? ?? ????? ?? 2 ?? GHS hazard pictograms P264, P280, P302+P352, P321,P332+P313, P362
H319 ?? ?? ??? ??? ?? ? ?? ?? ??? ?? ?? 2A ?? GHS hazard pictograms P264, P280, P305+P351+P338,P337+P313P
H335 ?? ???? ??? ? ?? ?? ???? ?? - 1? ??;???? ?? ?? 3 ?? GHS hazard pictograms
??????:
P261 ??·?·??·???·??·...·????? ??? ????.
P280 ????/???/???/?????? ?????.
NFPA 704
1
0 0

beta-D-Ribofuranose 1,2,3,5-tetraacetate MSDS


beta-D-Ribofuranose 1,2,3,5-tetraacetate

beta-D-Ribofuranose 1,2,3,5-tetraacetate C??? ??, ??, ??

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beta-D-Ribofuranose 1,2,3,5-tetraacetate is an acetylated derivative of ribose extensively used in carbohydrate research and synthetic chemistry. This compound features acetyl groups protecting the hydroxyl functionalities at positions 1, 2, 3, and 5 of the ribofuranose ring, which enhances its stability and solubility in organic solvents. β-D-Ribofuranose 1,2,3,5-tetraacetate is a crucial intermediate in synthesising nucleosides, nucleotides, and other complex carbohydrates. In research, it is utilized to study glycosylation mechanisms, focusing on the formation and stereochemistry of glycosidic bonds.

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beta-D-Ribofuranose 1,2,3,5-tetraacetate is white to almost white crystalline powder

??

beta-D-Ribofuranose 1,2,3,5-tetraacetate is used in the synthesis of 3-(β-D-ribofuranosyl)-2,3-dihydro-6H-1,3-oxazine-2,6-dione, a new pyrimidine nucleoside analog related to uridine.

?? ??

beta-D-Ribofuranose 1,2,3,5-tetraacetate, also known as 1,2,3,5-tetra-O-Acetyl-beta-D-ribofuranose (TAR), is an important organic reagent that can be used in the following pathways:
(1) Used in low-energy electron-induced reactions in gas-phase TAR. Since the acetyl group in TAR is coupled to the five-membered ribose ring at relevant positions, it can serve as a suitable model compound for studying the reaction of sugar units in DNA to low-energy electrons[1].
(2) Used to prepare 1,2,3-tri-O-acetyl-β-d-ribofuranose by enzymatic deacetylation[2].
(3) Used in condensation reactions. In the presence of tin chloride, 1-hexene reacts with 1- O -acetyl-2,3,5-tri- O -benzoyl-β- d -ribofuranose ( 5b ) or 1,2,3,5-tetra- O -acetyl-β- d -ribofuranose ( 5a ) to form a complex mixture[3].

beta-D-Ribofuranose 1,2,3,5-tetraacetate ?? ?? ? ???

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beta-D-Ribofuranose 1,2,3,5-tetraacetate ?? ??

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beta-D-Ribofuranose 1,2,3,5-tetraacetate ?? ??:

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