| DIISOPROPYLSILYL BIS(TRIFLUOROMETHANESULFONATE) Basic information |
| Product Name: | DIISOPROPYLSILYL BIS(TRIFLUOROMETHANESULFONATE) |
| Synonyms: | DIISOPROPYLSILYL BIS(TRIFLUOROMETHANESULFONATE);TRIFLUOROMETHANESULFONIC ACID DIISOPROPYLSILYLENE ESTER;DIISOPROPYLSILYL BIS(TRIFLUOROMETHANE-SU LFONATE), TECH.;diisopropylbis(trifluoromethanesulfonyl)silane;Bis(trifluoromethanesulfonic acid)diisopropylsilanediyl ester;Diisopropylsilylenebis(trifluoromethanesulfonate);Methanesulfonic acid, trifluoro-, bis(1-methylethyl)silylene ester;Methanesulfonic acid, 1,1,1-trifluoro-, bis(1-methylethyl)[[(trifluoromethyl)sulfonyl]oxy]silyl ester |
| CAS: | 85272-30-6 |
| MF: | C8H14F6O6S2Si |
| MW: | 412.4 |
| EINECS: | |
| Product Categories: | |
| Mol File: | 85272-30-6.mol |
| DIISOPROPYLSILYL BIS(TRIFLUOROMETHANESULFONATE) Chemical Properties |
| Boiling point | 85-86 °C2 mm Hg(lit.) |
| density | 1.396 g/mL at 25 °C(lit.) |
| refractive index | n |
| Fp | >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 Information |
| Provider | Language |
|---|---|
| SigmaAldrich | English |
| 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) Preparation Products And Raw materials |
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