NorrChemica™
3',5'-Di-O-pivaloylthymidine
3',5'-Di-O-pivaloylthymidine | PubChem CID: 10873286 | ≥98%
Pack sizes & prices
| Pack size | Excl. VAT | Add to cart |
|---|---|---|
| 500 mg−59% | ||
| 1.0 g−65% | ||
| 2.0 g−64% | ||
| 5.0 g−63% | ||
| 10 g−64% |
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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. |
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
| Safety Data Sheet | Download PDF |
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