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HomeProduct name listDIISOPROPYLSILYL BIS(TRIFLUOROMETHANESULFONATE)

DIISOPROPYLSILYL BIS(TRIFLUOROMETHANESULFONATE)

Synonym(s):Trifluoromethanesulfonic acid diisopropylsilylene ester

DIISOPROPYLSILYL BIS(TRIFLUOROMETHANESULFONATE) Structural

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.Coupling of products 5a–d

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  n20/D 1.382(lit.)
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)
ghs
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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