A B HO Write the missing product or reagent in each of the following: HO OTBDPS NHBoc H N-Boc En 0. i-ProTMS, TMSOTY, CH₂Cl₂ It, 24 h 0 (Hint: Think of TMS as a big proton. These conditions are dehydrating.) Olde D HOH C Ome =Ph (DHQ)₂PHAL (0.01 eq) K₂ Os 042H₂0 (0.005 eq) K₂Fe(CN) (3 eq) K₂CO, (3 eq) CH₂SO₂NH₂ (1 eq) t-BuOH:H₂0 (1:1) 0°C, 22 h DMSO, (COCI), CH₂Cl₂ E₂N, -78°C to It G A B E TBAF, THF, 3 h, it Ade, C(Ode) (4 eq) TsOHH₂0 (0.05 eq) CH₂Cl₂, 50°C, 25 h F

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Chapter1: Chemical Foundations
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A
B
HO
Write the missing product or reagent in each of the following:
HO
OTBDPS
NHBoc
H
N-Boc
En 0,
i-ProTMS, TMSOTY, CH₂Cl₂
It, 24 h
0
(Hint: Think of TMS as a big
proton. These conditions are
dehydrating.)
Olde
D
H OH
C
Ome
=Ph
(DHQ)₂PHAL (0.01 eq)
K₂ Os 042H₂0 (0.005 eq)
K₂Fe(CN) (3 eq)
K₂CO, (3 eq)
CH₂SO₂NH₂ (1 eq)
t-BuOH:H₂0 (1:1)
0°C, 22 h
DMSO, (COCI), CH₂Cl₂
E₂N, -78°C to It
G
A
B
E
TBAF, THF, 3 h, it
Ade, C(Ode) (4 eq)
TsOHH₂0 (0.05 eq)
CH₂Cl₂, 50°C, 25 h
F
Transcribed Image Text:A B HO Write the missing product or reagent in each of the following: HO OTBDPS NHBoc H N-Boc En 0, i-ProTMS, TMSOTY, CH₂Cl₂ It, 24 h 0 (Hint: Think of TMS as a big proton. These conditions are dehydrating.) Olde D H OH C Ome =Ph (DHQ)₂PHAL (0.01 eq) K₂ Os 042H₂0 (0.005 eq) K₂Fe(CN) (3 eq) K₂CO, (3 eq) CH₂SO₂NH₂ (1 eq) t-BuOH:H₂0 (1:1) 0°C, 22 h DMSO, (COCI), CH₂Cl₂ E₂N, -78°C to It G A B E TBAF, THF, 3 h, it Ade, C(Ode) (4 eq) TsOHH₂0 (0.05 eq) CH₂Cl₂, 50°C, 25 h F
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