692740-50-4

Upstream product

• 156769-28-7 methyl 2,3,4-tri-O-benzyl-6-deoxy-α-D-galactopyranoside 
• 75-08-1 ethanethiol 
• 50711-27-8 methyl 2,3-di-O-benzyl-4-deoxy-β-L-threo-pent-4-enopyranoside 
• 13231-27-1 Methyl-2,3-di-O-benzyl-6-desoxy-α-D-galactopyranosid 
• 444600-12-8 (1S,3S,4R,5R,6R)-4,5-Bis-benzyloxy-3-methoxy-2,7-dioxa-bicyclo[4.1.0]heptane 
• 17791-36-5 methyl 2,3-di-O-benzyl-α-D-glucopyranoside 
• 50711-26-7 methyl 2,3-di-O-benzyl-α-D-glucopyranosiduronic acid 

Downstream Products

• 692740-49-1 methyl 2-acetamido-2-deoxy-3,6-di-O-benzyl-4-O-[3,4,6-tri-O-benzyl-2-O-(2,3,4-tri-O-benzyl-α-D-fucopyranosyl)-β-L-galactopyranosyl]-β-L-glucopyranoside 
• 1202398-99-9 methyl 2,3,4-tri-O-benzyl-6-deoxy-β-L-altropyranoside 
• 1417781-43-1 methyl 2,3,4-tri-O-benzyl-6-deoxy-α-L-altropyranoside 
• 1417781-40-8 5-O-benzoyl-2,3,4-tri-O-benzyl-6-deoxy-L-altrose diethyl dithioacetal 

Relevant academic research and scientific papers

Synthesis of L-altrose and some derivatives

A convenient approach to the chemical synthesis of L-altrose (1) and its 6-deoxy derivative 2 has been developed by starting from D-galactose (9) and D-fucose (10), respectively. The 5-epimerization by a Mitsunobu inversion of the open-chain D-hexoses was the key step for these routes. Furthermore, the conversion of 2 into peracetylated TDP-6-deoxy-α-L-altrose (3a) was achieved by the cycloSal approach. However, the final deacetylation led to an unexpected side-reaction resulting in the previously unknown 6-deoxy-α-L-altropyranose 1,3-cyclophosphate (4).

Mirror-Image Carbohydrates: Synthesis of the Unnatural Enantiomer of a Blood Group Trisaccharide

Methyl D-glucoside and D-glucose pentaacetate are transformed, respectively, into methyl α-O-glucuronide 3 and hydroxymethyl β-C-glucuronide 9, which undergo decarboxylative elimination efficiently to produce 4-deoxypentenoside 4 and L-glucal 10. These unsaturated pyranosides provide an expeditious entry into mirror-image oligosaccharides, as demonstrated in the synthesis of the unnatural enantiomer of the H-type II blood group determinant trisaccharide (D-Fuc-(α1-2)-L-Gal-(β 1-4)-L-GlcNAc-β-OMe). This work illustrates that D-glucose, a common starting material in the synthesis of naturally occurring carbohydrates, can also be used to prepare their mirror-image analogues.