1.0 Natural Saccharides - digitoxin, kanamycin, salicin, glucose, sucrose, mannose

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1.1 nomenclature
simplest sugar glyceraldehyde - L and D stereochemistry

1.1 nomenclature II
keto-aldo-ose - pyranoses, furanoses

1.2 structure and conformation of monosaccharides

1.21 mechanism of hemiacetal formation
mutarotation of hemi-acetals, reasons and mechanism

1.22 Preferred chair conformation of pyranoses

1.23 Anomeric effect - Evidence, Explanation

1.23 Anomeric Effect II

1.23 Anomeric Effect III

1.3 Carbonyl group reactions

1.31 Carbonyl Group Reactions

1.31 Carbonyl Reactions II Oxidation/Reduction
oxidation - halogens, Ag+, to aldonic acids (lactones)
reduction to alditols

1.31 Synthesis of Chiral Starting materials

1.31 Carbonyl Reactions III Chain Shortening/Lengthening
condenstions- Killiani-Fischer extension, Wohl degradation

1.32 Acetal formation - Glycosides

1.32 Directed Glycoside Formation
formation of trans 1,2 substituents

1.32 In Situ Anomerisation
formation of cis 1,2 substituents

1.32 Glycoside Formation Summary
Glycoside formation - 4 x 1,2 regioisomers

1.4 Reactions of alcohols - see section 2

2.0. Protecting Groups

2.1 Protecting Groups for alcohols

Me ether
Bn ether

2.11 Ethers
for primary - Tr ether
for primary - silyl ether - TIPS
2.12 Alkylidenes for cis diols


2.13 Esters - Acetate and Benzoate

2.2 Protection for Amines - benzyl amine

2.21 Carbamates Cbz, Boc and Fmoc

2.3 Protection for Carboxylates - methyl, tert-butyl esters

2.31 Benzyl Ester

2.4 Summary table of deprotection conditions

3.0 Amino Acids - insulin, protease inhibitors, penicillin, aspartame, vasopressin, oxytocin

3.01 HIV Protease binding a peptide inhibitor

3.1 nomenclature
structures - natural amino acids - acid / base/ hydrophobic/phillic
L and D, R and S stereochemistry

3.2 Synthesis of amino acids

3.21 Strecker synthesis
3.22 alpha-bromination / Amination / Gabriel synthesis.
3.23 Alkylation of Glycine Synthons
3.24 Enzyme resolution of racemates
3.25 Asymmetric Amino Acid Synthesis - Seebach methodology

3.3 Peptide Synthesis - carboxyl activation

3.31 In Situ activation - DCC / DMAP and BOP
3.32 Activated Esters

4.0 Synthetic examples

4.1 Synthesis of Oxytocin

4.2 Oligosaccharide library synthesis
4.2 Oligosaccharide library synthesis II

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