c) Study the following reaction scheme for the preparation of a natural glycoside (compound 7) and answer the questions that follow: OH OAc excess Ac,0 AcO´ НО HO pyridine, 0°C -OH AcO -OAc OH `OAc Compound 3 Compound 4 HBr OCH3 OAc OAc AcO AcO AcO AcO- OAc OAc Compound 6 Compound 5 Br NaOH, H2O OCH3 OH НО HO Compound 7

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter21: Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions
Section21.SE: Something Extra
Problem 41MP
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c) Study the following reaction scheme for the preparation of a natural glycoside
(compound 7) and answer the questions that follow:
OH
OAc
Но
excess Ac20
AcO
pyridine, 0°C
HO-
Но.
AcO-
-OAc
`0Ac
HO
Compound 3
Compound 4
HBr
OCH3
OAc
OAc
AcO'
AcO
AcO
AcO-
OAc
OAc
Compound 6
Compound 5
Br
NaOH, H2O
OCH3
Он
HO
НО
Compound 7
ii.
Identify the unknown reagent(s) in the reaction scheme which converts compound 5 to
compound 6.
Transcribed Image Text:c) Study the following reaction scheme for the preparation of a natural glycoside (compound 7) and answer the questions that follow: OH OAc Но excess Ac20 AcO pyridine, 0°C HO- Но. AcO- -OAc `0Ac HO Compound 3 Compound 4 HBr OCH3 OAc OAc AcO' AcO AcO AcO- OAc OAc Compound 6 Compound 5 Br NaOH, H2O OCH3 Он HO НО Compound 7 ii. Identify the unknown reagent(s) in the reaction scheme which converts compound 5 to compound 6.
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