5'-O-Tert-butyldimethylsilyl-thymidine

Base Information

• Chemical Name: 5'-O-Tert-butyldimethylsilyl-thymidine
• CAS No.: 40733-28-6
• Molecular Formula: C16H28N2O5Si
• Molecular Weight: 356.494
• Hs Code.: 2933599090
• European Community (EC) Number: 807-001-2
• DSSTox Substance ID: DTXSID401239733
• Nikkaji Number: J406.690A
• Mol file: 40733-28-6.mol

Synonyms:40733-28-6;5'-O-TERT-BUTYLDIMETHYLSILYL-THYMIDINE;5'-O-TBDMS-dT;5'-O-(tert-Butyldimethylsilyl)thymidine;5'-O-tert-Butyldimethylsilylthymidine;1-[(2R,4S,5R)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-hydroxyoxolan-2-yl]-5-methylpyrimidine-2,4-dione;1-((2R,4S,5R)-5-(((tert-butyldimethylsilyl)oxy)methyl)-4-hydroxytetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione;5'-O-(t-Butyldimethylsilyl)thymidine;SCHEMBL888122;IJWIJLIIOKZJMS-YNEHKIRRSA-N;5'-o-t-butyldimethylsilylthymidine;DTXSID401239733;AMY24678;LT0131;MFCD01631041;AKOS037621905;5'-O-(tertbutyldimethylsilyl)thymidine;5'-O-(tert-butyldimethylsilyl) thymidine;AC-32241;AS-63732;BP-58687;PD157767;HY-138597;5'--O--(tert-butyldimethylsilyl) thymidine;CS-0159276;5-O-(tert-Butyldimethylsilyl)thymidine,98+%;D86090;5'-O-[(1,1-Dimethylethyl)dimethylsilyl]thymidine;5 inverted exclamation marka-O-[(1,1-Dimethylethyl)dimethylsilyl]thymidine;5invertedexclamationmarka-O-[(1,1-Dimethylethyl)dimethylsilyl]thymidine;1-((2R,4S,5R)-5-((tert-butyldimethylsilyloxy)methyl)-4-hydroxytetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione;1-[(2R,4S,5R)-5-{[(tert-butyldimethylsilyl)oxy]methyl}-4-hydroxyoxolan-2-yl]-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione

Chemical Property of 5'-O-Tert-butyldimethylsilyl-thymidine

Chemical Property:

• Melting Point: 198 °C
• Refractive Index: 1.507
• Boiling Point: 497.4oC at 760mmHg
• PKA: 9.55±0.10(Predicted)
• Flash Point: 254.6oC
• PSA: 93.55000
• Density: 1.148 g/cm³
• LogP: 1.51520
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 356.17674853
• Heavy Atom Count: 24
• Complexity: 555

Purity/Quality:

98%,99%, ^*data from raw suppliers

5'-O-tert-Butyldimethylsilylthymidine 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CN(C(=O)NC1=O)C2CC(C(O2)CO[Si](C)(C)C(C)(C)C)O
• Isomeric SMILES: CC1=CN(C(=O)NC1=O)[C@H]2C[C@@H]([C@H](O2)CO[Si](C)(C)C(C)(C)C)O
• Description: 5'-O-(tert-Butyldimethylsilyl)thymidine is a synthetic nucleoside that is used as an antiviral agent in the treatment of herpes zoster and other viral infections. 5'-O-tert-Butyldimethylsilyl-D3-thymidine is a novel monophosphate, which can be activated to a diphosphate by either kinases or phosphoramidites. It has been shown to be effective against herpes virus and other DNA viruses that infect cells from various species.
• Uses: 5'-O-(tert-Butyldimethylsilyl)thymidine is used as pharmaceutical intermediate.

Technology Process of 5'-O-Tert-butyldimethylsilyl-thymidine

There total 2 articles about 5'-O-Tert-butyldimethylsilyl-thymidine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 42.0%

C10H14N2O5SiC6H14PO2CH3 (236754-86-2) + (E)-6'-bromo-(5'-deoxy-5'-methylidene)-3'-O-(tert-bytuldiphenylsilyl)thymidine (236754-84-0) → 5'-tert-butyldimethylsilyloxy-2'-deoxythymidine (40733-28-6) + C10H14N2O4CSiC16H16C10H14N2O5PO2CH3SiC6H14 (289711-56-4)

Guidance literature:

With triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)00653-5

Reference yield: 18.0%

3',5'-O-di(tert-butyldimethylsilyl)thymidine (40733-26-4) → 3'-O-(t-butyldimethylsilyl)thymidine (40733-27-5) + 5'-tert-butyldimethylsilyloxy-2'-deoxythymidine (40733-28-6) + thymidine (50-89-5,28854-96-8,3545-96-8,50-88-4)

Guidance literature:

With phosphomolybdic acid; In acetonitrile; at 20 ℃; for 0.25h; regioselective reaction;

DOI:10.1055/s-0037-1610300

Reference yield: 100.0%

benzoyl chloride (98-88-4) + 5'-tert-butyldimethylsilyloxy-2'-deoxythymidine (40733-28-6) → 5'-O-(tert-butyldimethylsilyl)-(N3-benzoyl)thymidine (235744-89-5)

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃; for 6h;

DOI:10.1039/c6ob01371f

upstream raw materials:

C₁₀H₁₄N₂O₅SiC₆H₁₄PO₂CH₃

(E)-6'-bromo-(5'-deoxy-5'-methylidene)-3'-O-(tert-bytuldiphenylsilyl)thymidine

3',5'-O-di(tert-butyldimethylsilyl)thymidine

Downstream raw materials:

Bis(o-chlorophenyl) 5'-O-(tert-butyldimethylsilyl)thymidine 3'-phosphate

Phosphoric acid benzotriazol-1-yl ester (2R,3S,5R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 2-chloro-phenyl ester

Phosphoric acid benzotriazol-1-yl ester (2R,3S,5R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 2,4-dichloro-phenyl ester

5'-O-<(1,1-Dimethylethyl)-dimethylsilyl>-3'-O-(phenoxythioxomethyl)thymidine

Refernces

• 1、 Abbas, Sahar,Hayes, Christopher J.. "An improved procedure for the synthesis of vinylphosphonate-linked nucleic acids". . p. 4513 - 4517. Retrieved 2007/10/03.