Chapter 24, Problem 24.46AP

Interpretation Introduction

(a)

Interpretation:

The synthesis of isotopically labeled compound, $\text{D-glucose}$, is to be stated.

Concept introduction:

Killani Fischer synthesis is the three step process. In the first step, an aldose is converted into two cyanohydrins with an increased asymmetric carbon in the carbon chain by reacting with $\text{HCN}$. In the second step, the cyanohydrins are further hydrolyzed to form aldonic acids. In the third step, the aldonic acids are finally reduced to yield two diastereomeric aldoses. The overall use of Killani Fischer synthesis is to synthesize two diastereomeric aldoses with an increased asymmetric carbon from an aldose.

Interpretation Introduction

(b)

Interpretation:

The synthesis of isotopically labeled compound, $\text{D-glucose}$ is to be stated.

Concept introduction:

Killani Fischer synthesis is the three step process. In the first step, an aldose is converted into two cyanohydrins with an increased asymmetric carbon in the carbon chain by reacting with $\text{HCN}$. In the second step, the cyanohydrins are further hydrolyzed to form aldonic acids. In the third step, the aldonic acids are finally reduced to yield two diastereomeric aldoses. The overall use of Killani Fischer synthesis is to synthesize two diastereomeric aldoses with an increased asymmetric carbon from an aldose.

Interpretation Introduction

(c)

Interpretation:

The synthesis of isotopically labeled compound, $\text{D-glucose}$ is to be stated.

Concept introduction:

Ruff degradation is a process in which an aldose is converted into another aldose containing one carbon less than the starting aldose. In this process, an aldose is converted into aldonic acid by oxidation with ${\text{Br}}_{\text{2}}{\text{/H}}_{\text{2}}\text{O}$ and $\text{Ca}{\left(\text{OH}\right)}_{\text{2}}$. The decarboxylation of calcium salt of aldonic acid occurs when it is treated with $\text{Fe}$ and ${\text{H}}_{\text{2}}{\text{O}}_{\text{2}}$ and results in the formation of an aldose containg a carbon atom less than the starting aldose.

Killani Fischer synthesis is a three step process: conversion of aldose into cyanohydrins; hydrolysis; and reduction. The overall use of Killani Fischer synthesis is to synthesize two diastereomeric aldoses with an increased asymmetric carbon from an aldose.