| Identification | Back Directory | [Name]
DIISOPROPYLSILYL BIS(TRIFLUOROMETHANESULFONATE) | [CAS]
85272-30-6 | [Synonyms]
DK412
diisopropylbis(trifluoromethanesulfonyl)silane
DIISOPROPYLSILYL BIS(TRIFLUOROMETHANESULFONATE)
Diisopropylsilylenebis(trifluoromethanesulfonate)
TRIFLUOROMETHANESULFONIC ACID DIISOPROPYLSILYLENE ESTER
DIISOPROPYLSILYL BIS(TRIFLUOROMETHANE-SU LFONATE), TECH.
Bis(trifluoromethanesulfonic acid)diisopropylsilanediyl ester
Methanesulfonic acid, trifluoro-, bis(1-methylethyl)silylene ester
Methanesulfonic acid, 1,1,1-trifluoro-, bis(1-methylethyl)[[(trifluoromethyl)sulfonyl]oxy]silyl ester | [Molecular Formula]
C8H14F6O6S2Si | [MDL Number]
MFCD00043111 | [MOL File]
85272-30-6.mol | [Molecular Weight]
412.4 |
| Chemical Properties | Back Directory | [Boiling point ]
85-86 °C2 mm Hg(lit.) | [density ]
1.396 g/mL at 25 °C(lit.) | [refractive index ]
n20/D 1.382(lit.) | [Fp ]
>230 °F | [form ]
liquid | [Specific Gravity]
1.396 | [Hydrolytic Sensitivity]
8: reacts rapidly with moisture, water, protic solvents | [BRN ]
3567500 |
| Hazard Information | Back Directory | [Physical properties]
bp 85–86°C/2mmHg;d 1.396 g cm?3; fp 110°C. | [Uses]
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. | [storage]
DIISOPROPYLSILYL BIS(TRIFLUOROMETHANESULFONATE) should be stored in the refrigerator under an inert atmosphere of argon or nitrogen. Special care should be used when handling since diisopropysilyl bis(trifluoromethanesulfonate) has been classified as a corrosive.
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