triisopropylsilyl-Cl reagent reacts only once with the starting material. Me Me HO OH Me NH₂ iPr iPr-Si-iPr DMAP (base) Et3N

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter10: Alcohols
Section: Chapter Questions
Problem 10.52P: Alcohols are important for organic synthesis, especially in situations involving alkenes. The...
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During many organic syntheses it is a common practice to introduce a silyl ether protecting group to mask the activity of an OH group. In
this example, the silyl group chosen is the triisopropylsilyl group. Draw the product of the following transformation, assuming that the
triisopropylsilyl-Cl reagent reacts only once with the starting material.
Me Me
HO
How
HO
H
"H
OH
OH
• Use the wedge/hash bond tools to indicate stereochemistry where it exists.
• For your convenience, the starting material has been drawn for you in the sketchpad.
NH₂
.Me
NH₂
iPr
iPr-Si-iPr
CI
DMAP (base)
Et3N
Sn [F
Transcribed Image Text:During many organic syntheses it is a common practice to introduce a silyl ether protecting group to mask the activity of an OH group. In this example, the silyl group chosen is the triisopropylsilyl group. Draw the product of the following transformation, assuming that the triisopropylsilyl-Cl reagent reacts only once with the starting material. Me Me HO How HO H "H OH OH • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • For your convenience, the starting material has been drawn for you in the sketchpad. NH₂ .Me NH₂ iPr iPr-Si-iPr CI DMAP (base) Et3N Sn [F
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