Page 308 - Advanced Organic Chemistry Part B - Reactions & Synthesis

280 (d)
Ph P HO
2
CHAPTER 3
Functional Group CH PPh from
2
Interconversion N 2 2 N CH OH
by Substitution,
) COC O
3 3
Including Protection and (CH ) COC O (CH 3 3
Deprotection
(e) H
PPh 2 HO H
Ph P CH 3 from H CH 3
2
CH 3 H CH 3 OH
(f) H OCH Ph CH 3
2
CH 3 from O
CH CH CH(SC H ) PhCH 2 O
2 5 2
2
2
H
N 3 OCH 3
(g) O CCH 3
2
CO H
HO 2
O CH CO CH 3 from C
2
2
H CH CO H
CO CH 3 2 2
2
(h) CH 3 CH 3
O OTBDMS O OTBDMS
O O OCH 3 from O OH OCH
C H C H 3
2 5
C H SO -p -C H NO 2 2 5 C H
2 5
2 5
6 4
2
)
(i) OC(CH 3 3 OC(CH )
3 3
from
PhCH OCH 2 O O PhCH OCH 2 O O
2
2
3.6. Indicate conditions that would be appropriate for the following transformations
involving introduction or removal of protective groups:
(a) CH 3 CH 3
CH 3 CH 3
OH OCH 2 OCH CH OCH 3
2
2
(CH ) CH (CH 3 2
) CH
3 2
O
(b) O
CH 3
CH 3
CH OH
CH 2 2
CH CH OTBDPS
2
2
O
CH 3
CH O
O OH 3
O OH
CH 3 O OH
CH 3 O OH