DIISOPROPYLSILYL BIS(TRIFLUOROMETHANESULFONATE) Chemical Properties

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

Hazard Codes 

C

Risk Statements 

34-37

Safety Statements 

26-36/37/39-45

RIDADR 

UN 3265 8/PG 2

WGK Germany 

3

F 

10-21

HazardClass 

8

PackingGroup 

III

MSDS

• Language:English Provider:SigmaAldrich

DIISOPROPYLSILYL BIS(TRIFLUOROMETHANESULFONATE) Usage And Synthesis

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.

DIISOPROPYLSILYL BIS(TRIFLUOROMETHANESULFONATE)(85272-30-6)Related Product Information

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