69304-37-6

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1,1,3,3-TETRAISOPROPYL-1,3-DICHLORODISILOXANE

Product Code: SIT7273.0

Cas No: 69304-37-6

750 g
$1,623.00
25 g
$429.00
5 g
$108.00
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Bridging Silicon-Based Blocking Agent

Used as a protecting group for reactive hydrogens in alcohols, amines, thiols, and carboxylic acids. Organosilanes are hydrogen-like, can be introduced in high yield, and can be removed under selective conditions. They are stable over a wide range of reaction conditions and can be removed in the presence of other functional groups, including other protecting groups. The tolerance of silylated alcohols to chemical transformations summary is presented in Table 1 of the Silicon-Based Blocking Agents brochure.

Tetraisopropyldichlorodisiloxane; Dichlorotetraisopropyldisiloxane; 1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane; TIPDS
  • Highly useful for protection of 3’,5’- dihydroxynucleosides
  • Protects 1,2-diequatorial diols
  • Summary of selective deprotection conditions is provided in Table 7 through Table 20 of the Silicon-Based Blocking Agents brochure

    • Specific Gravity: 0.986

    Flashpoint: 76°C (169°F)

    HMIS Key: 3-2-1-X

    Hydrolytic Sensitivity: 8: reacts rapidly with moisture, water, protic solvents

    Formula: C12H28Cl2OSi2

    Refractive Index: 1.4543

    Application: Review of synthetic utility.1
    Review on organosilane protecting groups.2
    Reagent for protection of 3',5' hydroxy nucleosides.3,4
    Key review in natural products synthesis.5
    Protects the four equatorial hydroxyls of inositol in a single step.6

    Reference: 1. Handbook of Reagents for Organic Synthesis, Reagents for Silicon-Mediated Organic Synthesis, Fuchs, P. L. Ed., John Wiley and Sons, Ltd., 2011, p. 230-233.
    2. Larson, G. L. “Silicon-Based Blocking Agents” Gelest, Inc. 2014.
    3. Kanaya, E. N. et al. Biochemistry 1987, 26, 7159.
    4. Markiewicz, W. J. Chem. Res. 1979, 24.
    5. Ziegler, T. et al. Trends Org. Chem. 1997, 6, 91.
    6. Martin-Lomas, M. et al. Eur. J. Org. Chem. 2000, 1539.

    Fieser: F&F: Vol. 16, p 125.