DIISOPROPYLSILYL BIS(TRIFLUOROMETHANESULFONATE)
Synonym(s):Trifluoromethanesulfonic acid diisopropylsilylene ester
- CAS NO.:85272-30-6
- Empirical Formula: C8H14F6O6S2Si
- Molecular Weight: 412.4
- MDL number: MFCD00043111
- SAFETY DATA SHEET (SDS)
- Update Date: 2023-06-07 08:28:39
What is DIISOPROPYLSILYL BIS(TRIFLUOROMETHANESULFONATE)?
Physical properties
bp 85–86°C/2mmHg;d 1.396 g cm?3; fp 110°C.
The Uses of DIISOPROPYLSILYL BIS(TRIFLUOROMETHANESULFONATE)
Diisopropylsilyl
bis(trifluoromethanesulfonate) has more recently been
used to prepare diisopropylsilyl-linked oligonucleotide analogs.
Silylation of 5'-O-(dimethoxytrityl)-2'-deoxynucleosides using
diisopropylsilyl bis(trifluoromethanesulfonate) and the hindered
base 2,6-di-t-butyl-4-methylpyridine (Dtbp) provided quantitative
yield of 3'-O-diisopropylsilanols (eq 2). Hence, silylation
of 5'-O-(dimethoxytrityl)thymidine, N6-benzoyl-2'-deoxy-5'-O-
(dimethoxytrityl)adenosine, N4-benzoyl-2'-deoxy-5'-O-(dimethoxytrityl)
cytidine, and N2-isobutyryl-2'-deoxy-5'-O-(dimethoxytrityl)
guanosine gave the desired products 5a–d in excellent
yields.
Coupling of products 5a–d with unprotected thymidine
resulted in formation of 3',5'-linked dinucleosides 6a–d selectively,
and the dimer 7 from reaction with secondary hydroxyl
group of thymidine was not observed (eq 3). Subsequent silylation
and coupling with another molecule of thymidine gave 3,5-
linked trinucleoside 8 in 76% yield (eq 4). A tetrathymidylate oligomer was prepared by 3'-O-silylation of 8 followed by
coupling with thymidine. Although no self-condensation was
observed, only 30% of the product 9 was obtained after purification
by preparative HPLC.
Preparation
conveniently prepared by the slow addition of 2 equiv of trifluoromethanesulfonic acid to a stirring mixture of chlorodiisopropylsilane, followed by direct distillation of the product from the reaction flask to yield the product as a pale yellow oil.
Properties of DIISOPROPYLSILYL BIS(TRIFLUOROMETHANESULFONATE)
Boiling point: | 85-86 °C2 mm Hg(lit.) |
Density | 1.396 g/mL at 25 °C(lit.) |
refractive index | n |
Flash point: | >230 °F |
Specific Gravity | 1.396 |
Hydrolytic Sensitivity | 8: reacts rapidly with moisture, water, protic solvents |
BRN | 3567500 |
Safety information for DIISOPROPYLSILYL BIS(TRIFLUOROMETHANESULFONATE)
Signal word | Danger |
Pictogram(s) |
Corrosion Corrosives GHS05 |
GHS Hazard Statements |
H314:Skin corrosion/irritation |
Precautionary Statement Codes |
P280:Wear protective gloves/protective clothing/eye protection/face protection. P363:Wash contaminated clothing before reuse. P303+P361+P353:IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. P405:Store locked up. |
Computed Descriptors for DIISOPROPYLSILYL BIS(TRIFLUOROMETHANESULFONATE)
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