NorrChemica™
3′,5′-Bis-O-(tert-butyldimethylsilyl)thymidine
3′,5′-Bis-O-(tert-butyldimethylsilyl)thymidine | CAS 40733-26-4 | ≥98%
Pack sizes & prices
| Pack size | Excl. VAT | Incl. VAT | Add to cart |
|---|---|---|---|
| 1.0 g−76% | |||
| 2.0 g−71% | |||
| 5.0 g−74% | |||
| 10 g−75% | |||
| 25 g−68% | |||
| 50 g−75% | |||
| 100 g−68% |
Taxes and fees, e.g. VAT, included in the price. Shipping calculated at checkout.Free shipping on EU, UK and EFTA orders above €250, and above €400 to the rest of the world.
Technical Specifications
| CAS Number | 40733-26-4 |
| MDL Number | MFCD01631042 |
| SMILES | CC1=CN(C(=O)NC1=O)[C@H]2C[C@@H]([C@H](O2)CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C |
| InChI | InChI=1S/C22H42N2O5Si2/c1-15-13-24(20(26)23-19(15)25)18-12-16(29-31(10,11)22(5,6)7)17(28-18)14-27-30(8,9)21(2,3)4/h13,16-18H,12,14H2,1-11H3,(H,23,25,26)/t16-,17+,18+/m0/s1 |
| InChIKey | DDLOCFSZSYGOPG-RCCFBDPRSA-N |
| PubChem CID | 10459624 |
| Molecular Formula | C₂₂H₄₂N₂O₅Si₂ |
| Molecular Weight | 470.75 g/mol |
| Solubility | Soluble in dichloromethane, chloroform, ethyl acetate, and THF; practically insoluble in water |
| Purity | ≥98% |
| Physical Form | White to off-white crystalline solid |
| HS Code | 2934.99 |
| Shelf Life | Retest period: 24 months from date of manufacture |
| Storage Conditions | Store at 2-8°C in a tightly sealed container, protected from moisture |
Product Description & Scientific Applications
3′,5′-Bis-O-(tert-butyldimethylsilyl)thymidine (3′,5′-bis-O-TBDMS-thymidine) is a fully sugar-protected thymidine derivative in which both the 3′- and 5′-hydroxyls of the 2′-deoxyribose are masked as TBDMS ethers. The protection holds through neutral, basic, and acylating conditions, while retaining the acid- and fluoride-lability of TBDMS ethers. Fluoride (TBAF or triethylamine trihydrofluoride) removes both silyl groups; controlled acidic hydrolysis removes the more accessible primary 5′-TBDMS ether selectively, giving 3′-O-TBDMS-thymidine with a free 5′-OH.
Nucleobase modification. With both sugar hydroxyls masked, base-directed chemistry proceeds without competing reaction at the 3′- or 5′-OH. The thymine ring is functionalised through N3-alkylation or temporary N3 acyl/carbamate protection. The C5-methyl group is an entry point for side-chain chemistry: radical bromination gives the bromomethyl intermediate, which displaces with O-, N-, S-, or C-nucleophiles to install ether, amine, thioether, or carbon-linked substituents. Fluoride deprotection then gives the base-modified thymidine.
Sugar modification. Selective 5′-desilylation gives a mono-protected intermediate for stepwise sugar work. The free 5′-OH is phosphorylated, tritylated, acylated, or tagged while the 3′-OH stays protected. In the free-3′ regiochemistry the 3′-OH is activated by mesylation, tosylation, oxidation-reduction, or fluorination, and sugar-modification chemistry delivers 3′-azido, 3′-fluoro, 3′-amino, 3′-deoxy, and 2′,3′-didehydro analogues. Fluoride desilylation releases the free analogue.
Monomer preparation. The compound is a modular intermediate for modified thymidine monomers, not the ordinary dT phosphoramidite precursor. After 5′-deprotection and installation of a 5′ handle, the 3′-TBDMS is removed and the 3′-OH converted into a phosphoramidite, H-phosphonate, phosphotriester, phosphorothioate, phosphorodithioate, or phosphoramidate precursor, including for sugar- or base-modified nucleotide analogues.
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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