88165-22-4

Upstream product

• 88165-21-3 benzyl 2,3-O-isopropylidene-5-O-trifluoromethylsulphonyl-α-D-lyxofuranoside 
• 20786-73-6 (6-benzyloxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol 
• 5927-18-4 trimethyl phosphonoacetate 

Downstream Products

• 138-59-0 shikimic acid 
• 40983-58-2 methyl shikimate 

Relevant academic research and scientific papers

Enantiospecific Synthesis of Shikimic Acid from D-Mannose: Formation of a Chiral Cyclohexene by Intramolecular Olefination of a Carbohydrate-derived Intermediate

An enantiospecific synthesis of (-)-shikimic acid from D-mannose in an overall yield of 39percent is described, in which the key step is an intramolecular Wadsworth-Emmons olefination reaction of a phosphonate.Nucleophilic displacement of triflate from benzyl 2,3-O-isopropylidene-5-O-trifluoromethylsulphonyl-α-D-lyxofuranoside by the sodium salt of t-butyl dimethoxyphosphorylacetate provides a rare example of substitution at the C-5 position of a furanose derivative by a carbanion.

An Entry to Chiral Cyclohexenes from Carbohydrates: A Short, Efficient, and Enantiospecific Synthesis of (-)-Shikimic Acid from D-Mannose

A short, efficient, and enantiospecific synthesis of (3R,4S,5R)-shikimic acid from benzyl 2,3-O-isopropylidene-α-D-lyxofuranoside (readily available from D-mannose) is described.