• Chemical structure of 3′,5′-Di-O-Pivaloylthymidine, ≥98% — pivaloyl-protected thymidine derivative used as a building block in oligonucleotide synthesis, nucleoside chemistry, and as a sugar-protected intermediate for selective modification of the thymine base. Supplied by NorrChemica with DDP shipping. CoA and SDS provided.​​​​​​​​​​​​​​​​
  • ¹H NMR spectrum of 3′,5′-Di-O-Pivaloylthymidine in DMSO-d₆ at 298.1 K, Bruker Avance 400.15 MHz, 20 s relaxation delay, 8 scans. Thymine N–H at ~11.3 ppm (1.00); C6–H at ~7.5 ppm (1.00); anomeric C1′–H at ~6.2 ppm (1.03); sugar C–H and CH₂ between ~4.0–5.3 ppm (1.01 + 1.01 + 1.04 + 1.01); thymine 5-CH₃ at ~1.8 ppm (1.04 + 1.02); pivaloyl C(CH₃)₃ at ~1.1 ppm (18.24). Confirms structure and ≥98% purity. Batch NOR55341406-25-2, NorrChemica.
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NorrChemica™

3',5'-Di-O-pivaloylthymidine

PubChem CID: 10873286 ≥98%

3',5'-Di-O-pivaloylthymidine | PubChem CID: 10873286 | ≥98%

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Technical Specifications

SMILES CC1=CN(C(=O)NC1=O)[C@H]2C[C@@H]([C@H](O2)COC(=O)C(C)(C)C)OC(=O)C(C)(C)C
InChI InChI=1S/C20H30N2O7/c1-11-9-22(18(26)21-15(11)23)14-8-12(29-17(25)20(5,6)7)13(28-14)10-27-16(24)19(2,3)4/h9,12-14H,8,10H2,1-7H3,(H,21,23,26)/t12-,13+,14+/m0/s1
InChIKey CDURWIFHJJVZIL-BFHYXJOUSA-N
PubChem CID 10873286
Molecular Formula C₂₀H₃₀N₂O₇
Molecular Weight 410.46 g/mol
Solubility Soluble in dichloromethane, chloroform, THF, and ethyl acetate; sparingly soluble in water.
Purity ≥98%
Physical Form White to off-white crystalline solid
HS Code 2934.99
Shelf Life Retest period: 36 months from date of manufacture.
Storage Conditions Store at room temperature in a tightly sealed container, protected from moisture

Product Description & Scientific Applications

3′,5′-Di-O-pivaloylthymidine (3′,5′-di-O-trimethylacetylthymidine) is a thymidine derivative in which both 3′- and 5′-hydroxyls of the 2′-deoxyribose are esterified as pivaloyl esters, while the thymine nucleobase is unprotected. It is a white to off-white crystalline solid, handled as a hydrophobic protected-nucleoside intermediate. Pivaloyl is among the most sterically demanding acyl protecting groups for sugar hydroxyls: the tert-butyl group adjacent to the carbonyl shields it from nucleophilic attack and slows nucleophilic acyl substitution relative to acetate, benzoate, and isobutyrate, giving the esters kinetic persistence under base hydrolysis, methanolysis, transesterification, and acyl-transfer conditions while remaining cleavable. The steric demand may also suppress acyl migration, though this is substrate- and condition-dependent. The group trades ease of removal for this persistence; compatibility with the nucleobase, phosphate, and final deprotection sequence must be established.

Orthogonality window. Its cleavage logic differs from the ether alternatives: unlike benzyl ether, removal needs no hydrogenolysis, so it suits sequences where catalytic hydrogenation is precluded; unlike silyl ethers (TBS, TBDPS, TIPS), it carries no fluoride-triggered cleavage or acid/moisture sensitivity. Double pivaloyl protection at both the 3′- and 5′-oxygens is an uncommon arrangement for thymidine, and this bulky-acyl pairing can underpin synthetic sequences not readily accessible with the more common sugar-protecting groups.

Shipping Destinations

  • EU & UK: Priority delivery, 2–5 business days.
  • United States (DDP): 3–7 business days, duties and taxes prepaid.
  • EFTA Countries (DDP): 3–7 business days, duties and taxes prepaid.
  • Worldwide: 7–14 business days, selected locations.

Safety Information

Hazard Class None — not subject to transport regulations
Transport Category Not classified as dangerous goods for transport (ADR/IATA/IMDG)

Documentation

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