188003-35-2

Upstream product

• 188003-23-8 (2S,3S,4S,5R,6R)-6-Benzyloxy-3,4,5-tris-(2,2-dimethyl-propionyloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 188003-25-0 (4S,5R,6R)-6-Benzyloxy-4,5-bis-(2,2-dimethyl-propionyloxy)-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester 
• 3080-47-5 methyl (benzyl 2,3,4-tri-O-acetyl-β-D-glucopyranosid)uronate 
• 108852-23-9 O¹-benzyl-β-D-glucopyranuronic acid methyl ester 
• 188003-31-8 (2R,3R,4R,5R,6R)-6-Benzyloxy-3-bromo-4,5-bis-(2,2-dimethyl-propionyloxy)-2-hydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester 

Downstream Products

• 188003-41-0 (2R,4R,5R,6R)-6-Benzyloxy-4,5-bis-(2,2-dimethyl-propionyloxy)-3-oxo-tetrahydro-pyran-2-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Regio and stereoselective conversion of Δ4-uronic acids to L-ido- and D-glucopyranosiduronic acids

Synthesis of L-ido- and D-glucopyranosiduronic acids was performed starting from protected Δ4-uronic acids 3a-f. Bromination of the C-4,5 double bond provided the trans-diaxial bromohydrin derivatives 6a-d, which were converted to the corresponding epoxides 7a-d in high yields. Direct reduction of these epoxides using borane-tetrahydrofuran complex afforded the D-glucopyranosiduronic acids 9b-d, while Lewis acid rearrangement through the C-4 keto intermediate 10b-d afforded the L-idopyranosiduronic acids 11b-d.