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Quality Control of Thymidine Purity: 98% SDS Specification

COA

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Batch number can be found on the product's label following the word 'Batch'.

NMR

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CNMR

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HPLC

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Product Citations

Organocatalytic conversion of nucleosides to furanoid glycals

Mao, Edna ; Chung, Cheol K ; Ji, Yining ; Lam, Yu-hong ; Maligres, Peter E ;

DOI: 10.1021/acs.joc.1c00555 PubMed ID: 34033478 JOC,2021,86(11):7529-7536.

Abstract: A class of organocatalysts that are highly active for the conversion of 2′-deoxynucleosides to furanoid glycals have been discovered. These phosphorimides, (Ph2PS)2NH and (Ph2PSe)2NH, were shown to effectively mediate persilylation of 2′-deoxynucleosides allowing the elimination of the nucleobase giving the corresponding glycal. These mild conditions were demonstrated in the syntheses of glycals with various substitution patterns while minimizing the formation of undesired byproducts and expanding the scope of this methodology.

Purchased from AmBeed: 50-89-5

Product Details of Thymidine

CAS No. :	50-89-5
Formula :	C₁₀H₁₄N₂O₅
M.W :	242.23
SMILES Code :	O=C1NC(C(C)=CN1[C@@H]2O[C@H](CO)[C@@H](O)C2)=O
Synonyms :	DThyd; NSC 21548; AI3-52267
MDL No. :	MFCD00006537
InChI Key :	IQFYYKKMVGJFEH-XLPZGREQSA-N
Pubchem ID :	5789

Safety of Thymidine

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302+H312+H332-H315-H319-H335
Precautionary Statements:	P261-P280-P305+P351+P338

Application In Synthesis of Thymidine

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 50-89-5 ]
Downstream synthetic route of [ 50-89-5 ]

[ 50-89-5 ] Synthesis Path-Upstream 1~2

1
[ 50-89-5 ]
[ 838-07-3 ]

Yield	Reaction Conditions	Operation in experiment
92%	Stage #1: With 1,8-diazabicyclo[5.4.0]undec-7-ene; ((3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V) In N,N-dimethyl-formamide at 20℃; for 0.0166667 h; Stage #2: With ammonium hydroxide In N,N-dimethyl-formamide at 20℃; for 2 h;	General procedure: To a solution of the nucleosides (2–20) in DMF ([substrate]=0.3M, except for 3 and 4, [3,4]=0.05M) were added PyAOP (1.6 eq) and DBU (1.6 eq). The reaction was stirred at 20°C for 1min. To the reaction solution was added N-nucleophiles (4 eq) (or 1a in THF, conc. NH₄OH (10 eq)). The reaction was stirred at 20°C for 5min−4h and monitored by TLC. Upon completion, the solution was concentrated in vacuo. Flash column chromatography on silica gel afforded ^5MedC and oxidized ^5MedC derivatives (1′–20′) in pure form.

References: [1] Tetrahedron, 2018, vol. 74, # 49, p. 7095 - 7101.
[2] Nucleosides and Nucleotides, 1996, vol. 15, # 4, p. 907 - 921.
[3] Journal of the American Chemical Society, 1959, vol. 81, p. 178,187.

2
[ 50-89-5 ]
[ 838-07-3 ]

References: [1] Gazzetta Chimica Italiana, 1983, vol. 113, # 11/12, p. 863 - 864.

[ 50-89-5 ] Synthesis Path-Downstream 1~24

1
[ 932-53-6 ]
[ 50-89-5 ]
[ 13410-30-5 ]

References: [1]Journal of the American Chemical Society,1958,vol. 80,p. 1138,1139,1140.

2
[ 94465-25-5 ]
[ 50-89-5 ]
[ 136345-26-1 ]

References: [1]Nucleosides and Nucleotides,1994,vol. 13,p. 1397 - 1414.

3
[ 50-89-5 ]
[ 5116-24-5 ]
[ 65-71-4 ]
[ 4494-26-2 ]

References: [1]Chemistry Letters,1991,p. 85 - 88.
[2]Chemistry Letters,1991,p. 85 - 88.
[3]Chemistry Letters,1991,p. 85 - 88.

4
[ 50-89-5 ]
[ 5116-24-5 ]
[ 4494-26-2 ]

References: [1]Bulletin of the Chemical Society of Japan,1994,vol. 67,p. 2257 - 2264.
[2]Bulletin of the Chemical Society of Japan,1994,vol. 67,p. 2257 - 2264.

5
2,2′-azobis(2-methylpropionamidine)dihydrochloride [ No CAS ]
[ 50-89-5 ]
3,3',4,4'-tetramethylsuccinimidine [ No CAS ]
[ 65-71-4 ]
[ 4494-26-2 ]
2-(2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-ylmethoxy)-2-methyl-propionamidine [ No CAS ]

References: [1]Chemical Research in Toxicology,1997,vol. 10,p. 234 - 241.

6
[ 50-89-5 ]
[ 5116-24-5 ]
[ 65-71-4 ]
[ 4494-26-2 ]
[ 38716-10-8 ]

References: [1]Chemical Research in Toxicology,1997,vol. 10,p. 234 - 241.

7
[ 180181-02-6 ]
[ 50-89-5 ]
BocNH-HE-T [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In chloroform; N,N-dimethyl-formamide; at 0 - 20℃; for 20h;	4-Boc-amino-2,2-dimethybutyric acid (compound 16, 0.50 g, 2.16 mmol) was dissolved in a mixture of chloroform (10 mL) and DMF (5 mL), and thymidine (compound 17, 0.79 g, 3.25 mmol) was added. The reaction mixture was cooled in an ice bath, and EDC (0.62 g, 3.25 mmol) was added, followed by DMAP (0.4Og, 3.25 mmol). The reaction mixture was allowed to warm to room temperature for 20 hours with stirring. Solvent was removed in <n="52"/>7 078597vacuo and the residue was suspended in ethyl acetate, washed with 0.1N HCl, and brine. Organic layer was dried over anhydrous sodium sulfate and the solvent was removed in vacuo to give a crude oil. Flash column chromatography on silica gel using DCM / EtOAc (40:60, v/v) gave 0.28 g of the desired product: 13C NMR d 177.21, 164.08, 156.41, 150.80, 135.46, 111.49, 85.43, 84.30, 80.21, 71.28, 63.77, 41.67, 41.08, 40.00, 37.69, 36.99, 28.87, 26.14, 25.55, 13.06.

References: [1]Patent: WO2008/34122,2008,A2 .Location in patent: Page/Page column 50-51.

8
[ 1077-58-3 ]
[ 50-89-5 ]
[ 1188380-10-0 ]

References: [1]Bioorganic and Medicinal Chemistry,2009,vol. 17,p. 5928 - 5932.

9
calf thymus DNA, γ-irradiated [ No CAS ]
[ 31077-24-4 ]
[ 105929-27-9 ]
[ 961-07-9 ]
[ 88847-89-6 ]
[ 117182-88-4 ]
(5'R)-5',8-cyclo-2'-deoxyadenosine [ No CAS ]
(5'R)-5',8-cyclo-2'-deoxyguanosine [ No CAS ]
[ 951-77-9 ]
[ 50-89-5 ]
[ 958-09-8 ]