CAS 40733-27-5 3'-O-(t-butyldimethylsilyl)thymidine (HCID 453844)

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Basic information

CAS: 40733-27-5
Standard SMILES: Cc1cn([C@H]2C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](CO)O2)c(=O)[nH]c1=O
InChIKey: QAPSNMNOIOSXSQ-YNEHKIRRSA-N
Molecular formula: C16H28N2O5Si
Average molar mass: 356.49 g/mol
Monoisotopic mass: 356.17674853

Names & identifiers

Preferred name: 3'-O-(t-butyldimethylsilyl)thymidine
IUPAC: 1-[(2R,4S,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
English name: 3'-O-(t-Butyldimethylsilyl)thymidine
Molecular formula: C16H28N2O5Si
Molecular weight: 356.49

Names & synonyms

40733-27-53'-O-(t-butyldimethylsilyl)thymidineDTXSID60332379RefChem:269413DTXCID002834721-((2R,4S,5R)-4-((tert-butyldimethylsilyl)oxy)-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dioneMFCD01631040Thymidine, 3'-O-[(1,1-dimethylethyl)dimethylsilyl]-3'-O-(TBDMS)THYMIDINE1-[(2R,4S,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione3'-O-t-BulyldiMethylsilyl thyMidine3'-O-TBDMS-dT

Show more names

3'-O-TBDMS-2'-dT3’-O-t-Bulyldimethylsilyl thymidine3'-O-[tert-Butyl(dimethyl)silyl]thymidine3'-O-tert-butyldiMethylsilyl-2'-deoxythyMidine

3'-O-(tert-butyldimethylsilyl)thymidine3'-O-t-BulyldiMethylsilylThymidine3'-O-t-Butyldimethylsilyl thymidineC16H28N2O5Si1-[(2R,4S,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-methyl-pyrimidine-2,4-dioneTBS-T3 inverted exclamation mark -O-t-Bulyldimethylsilylthymidine3'-DiTBSRiboT

Properties

Computed structural properties

Topological polar surface area: 88.1 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 5
Rotatable bonds: 5
Heavy atoms: 24
Formal charge: 0
Complexity: 555

Physicochemical properties

Melting point: 93 · 93-94 °C
Density: 1.17 · 1.17±0.1 g/cm3(Predicted)
storage temp.: 2 · 2-8°C
pka: 9.55 · 9.55±0.10(Predicted)
form: Solid
color: White to off-white
optical activity: 22.1 ° · 22.1° (C=0.01 g/ml, CHCL3)
InChI: InChI=1S/C16H28N2O5Si/c1-10-8-18(15(21)17-14(10)20)13-7-11(12(9-19)22-13)23-24(5,6)16(2,3)4/h8,11-13,19H,7,9H2,1-6H3,(H,17,20,21)/t11-,12+,13+/m0/s1
InChIKey: QAPSNMNOIOSXSQ-YNEHKIRRSA-N
SMILES: OC[C@H]1O[C@@H](N2C=C(C)C(=O)NC2=O)C[C@@H]1O[Si](C(C)(C)C)(C)C
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 302 · H302-H315-H319
Precautionary statements: 261 · P261-P305+P351+P338

Safety & regulation

Safety data

Signal word: Warning
Symbol(GHS): GHS07
Hazard statements: H302-H315-H319
Precautionary statements: P261-P305+P351+P338

Chemistry & industry

Applications · 2 items

Description3'-O-[tert-Butyl(dimethyl)silyl]thymidine is a nucleoside analog that is chemically stable and has been shown to be a potential biomarker for the diagnosis of fetal bovine spongiform encephalopathy (BSE). 3'-O-t-Bulyldimethylsilyl thymidine binds to basic proteins in the cell nucleus and has been shown to inhibit protein synthesis in tubule cells of the kidney and skin cancer cells.

Uses3’-O-t-Bulyldimethylsilylthymidine is a purine nucleoside analog. Purine nucleoside analogs have broad antitumor activity targeting indolent lymphoid malignancies. Anticancer mechanisms in this process rely on inhibition of DNA synthesis, induction of apoptosis, etc[1].