2,2'-Anhydro-5-methyluridine
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2,2'-Anhydro-5-methyluridine
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CAS No:
22423-26-3
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Formula:
C10H12N2O5
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Chemical Name:
2,2'-Anhydro-5-methyluridine
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Synonyms:
2,2'-cyclo-5-methyluridine;2,2'-Anhydrothimidine;Uridine,2,2'-cyclo-5-methyl;2,2'-Anhydro-D-thymidine;2,2’-Cryclo-5-methyluridine;2,2''-Anhydro-(1-beta-D-arabinofuranosyl)-5-methyluracil;6H-Furo[2'',3'':4,5]oxazolo[3,2-a]pyrimidin-6-one, 2,3,3a,9a-tetrahydro-3-hydroxy-2-(hydroxymethyl)-7-methyl-, (2R,3R,3aS, 9aR)-;(2R)-2,3,3aβ,9aβ-Tetrahydro-3β-hydroxy-2α-(hydroxymethyl)-7-methyl-6H-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-6-one
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CAS No:
2,2'-Anhydro-5-methyluridine Basic Attributes
240.21
240.074615
2017-001-1
GQZ99GWR3T
White to Almost white
2940.00.6000
Characteristics
91.6
-2.1
white or almost white crystalline powder
1.88±0.1 g/cm3(Predicted)
217.0 to 221.0 °C
452.0±55.0 °C(Predicted)
227.2±31.5 °C
1.773
Soluble in water
4.54E-10mmHg at 25°C
12.56±0.60(Predicted)
Sealed in dry,Room Temperature
2,2'-Anhydro-5-methyluridine Use and Manufacturing
The reaction flask was charged with DMF 100 mL, 5-methyluridine (50.0 g, 0.19 mol), sodium hydroxide (0.18 g, 4.4mmo 1) and diethyl carbonate (46mL, 0.38mo 1), heated to 120 ° C, the reaction was incubated for 8 hours. After the reaction of TLC detection material was completed, the temperature was lowered to room temperature, the pH was adjusted to neutral (about 7.0) with 30percent hydrochloric acid in ethanol and concentrated to dryness. The concentrate was added with 50 mL of ethyl acetate and refluxed for 1 hour, cooled to room temperature, filtered and the solid was collected. The solid was dried under vacuum at 60 ° C to give the title compound (white solid, 44.5 g) in a molar yield of 95.6percent and HPLC purity of 98.29.percentThe scheme below shows the synthesis of the 2′-DIBO-5-methyluridine phosphoramidite compound B: (i) diphenyl carbonate, NaHCO5-Methyluridine (ribosylthymine, commercially available through Yamasa, Choshi, Japan) (72.0 g, 0.279 M), diphenylcarbonate (90.0 g, 0.420 M) and sodium bicarbonate (2.0 g, 0.024 M) were added to DMF (300 mL). The mixture was heated to reflux, with stirring, allowing the evolved carbon dioxide gas to be released in a controlled manner. After 1 hour, the slightly darkened solution was concentrated under reduced pressure. The resulting syrup was poured into diethylether (2.5 L), with stirring. The product formed a gum. The ether was decanted and the residue was dissolved in a minimum amount of methanol (ca. 400 mL). The solution was poured into fresh ether (2.5 L) to yield a stiff gum. The ether was decanted and the gum was dried in a vacuum oven (60° C. at 1 mm Hg for 24 h) to give a solid that was crushed to a light tan powder (57 g, 85percent crude yield). The NMR spectrum was consistent with the structure, contaminated with phenol as its sodium salt (ca. 5percent). The material was used as is for further reactions (or it can be purified further by column chromatography using a gradient of methanol in ethyl acetate (10-25percent) to give a white solid, mp 222-4° C.).5-methyluridine (3) (15 g, 58.06 mmol) was dissolvedin dry dimethylformamide (100 mL) and treated with dimetyl carbonate (6.95 mL, 81.87 mmol) and sodium hydrogen carbonate (0.31 g, 3.71 mmol). The mixture was heated at 130 °C for 2 h and poured into ether. The precipitated gum was then crystallized from methanol to give the 2, 2’-anhydrothymidine (4) as colorless prisms (10.9 g, 78percent); [α]See: J. Med. Chem. 1979, 22, 1273-1277. To a round bottom flask containing 21 (10 g, 38.6 mmol) in DMF 20 mL, was added (PhO)2, 2'-Anhydro[1-(beta-D-arabinofuranosyl)-5-methyluridine] Synthesis of 2, 2Example 3
Computed Properties
Molecular Weight:240.21
XLogP3:-2.1
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:1
Exact Mass:240.07462149
Monoisotopic Mass:240.07462149
Topological Polar Surface Area:91.6
Heavy Atom Count:17
Complexity:432
Defined Atom Stereocenter Count:4
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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