The Wohl degradation, shown in Fig. P24.51, can be used to convert an aldose into another aldose
Question:
The Wohl degradation, shown in Fig. P24.51, can be used to convert an aldose into another aldose with one fewer carbon. Give the structure of the missing compounds as well as the curved-arrow mechanisms for the conversion of B to C and C to arabinose.
Transcribed Image Text:
H- НО- H H CH O -OH -H -OH -OH CH₂OH Figure P24.51 NH₂OH A an oxime excess Ac₂0 B C18H25O12N H- AcO- H- H- Na+ ACO C=N C -OAc H -OAC -OAC CH₂OAC Na CH₂O. HO- H- H- CH O -H -OH -OH CH₂OH D-arabinose
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Compound A is the corresponding oxime see Table 193 on text p 985 and compound B results from acetyl...View the full answer
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