Chapter 24, Problem 24.47AP

Interpretation Introduction

Interpretation:

The structure of compound $A$ which is a monomethyl ether of $\text{D-glucose}$ 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 the 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.