150575-74-9

Upstream product

• 78136-16-0 2,3,4,6-tetra-O-benzyl-D-glucitol 
• 100-39-0 benzyl bromide 
• 21730-93-8 L-threonic acid-4-lactone 
• 81927-55-1 O-benzyl 2,2,2-trichloroacetimidate 
• 97506-01-9 (3R,4R)-3,4-bis(benzyloxy)-3,4-dihydro-2,5-furandione 
• 896448-10-5 (2R,3R)-2,3-Bis-benzyloxy-succinic acid monomethyl ester 

Downstream Products

• 113427-43-3 1,4-di-O-benzyl-L-threitol 

Relevant academic research and scientific papers

Synthesis of a Threosyl-C-nucleoside Phosphonate

A general synthetic route for the preparation of the first analogue of a new series of sugar-modified C-nucleoside phosphonates is detailed. Such derivative contains a four-carbon l-threose sugar moiety substituted with a phosphonomethoxy group at the 3′-position and pyrrolo[2,1-f][1,2,4]triazin-4-amine as nucleobase. A C-nucleoside was initially prepared by coupling a benzyl protected l-threono-1,4-lactone intermediate with the corresponding aglycon moiety. The choice of a tert-butyldiphenylsilyl group was found to be crucial to achieve the regioselective protection of the hydroxyl group at the 3′-position. Moreover, it allowed to smoothly perform further synthetic manipulations, including the introduction of a benzyl protected phosphonate synthon under basic conditions, which eventually led to the desired compound after final deprotection.

Synthesis of 4-membered carbasugars by way of stereoselective SmI 2-mediated aldehyde-alkene cyclization

A stereodivergent synthesis of the first examples of 4-membered carbasugars has been achieved from vitamin C by way of an efficient intramolecular SmI 2-mediated aldehyde-alkene coupling. In this key step, cylobutanes with four contiguous asymmetric centers are generated with a high level of stereocontrol.

Synthesis of glycaro-1,5-lactams and tetrahydrotetrazolopyridine-5- carboxylates: Inhibitors of β-D-glucuronidase and α-L-iduronidase

The known glucaro-1,5-lactam 8, its diastereoisomers 9-11, and the tetrahydrotetrazolopyridine-5-carboxylates 12-14 were synthesised as potential inhibitors of β-D-glucuronidases and α-L-iduronidases. The known 2,3-di-O-benzyl-4,6-O-benzylidene-D-galactos

Displacement Reactions on 2,3,4,6-Tetra-O-benzyl-1,5-di-O-sulfonyl-D-glucitols. Synthesis of (3R,4S)-3,4-Dibenzyloxy-2-(2-benzyloxyethylidene)tetrahydrofuran

Treatment of the 1,5-dimesylate and 1,5-ditosylate of 2,3,4,6-tetra-O-benzyl-D-glucitol 1 with tetrabutylammonium acetate in acetonitrile leads, through nucleophilic attack by O-2 at C-5 and normal displacement at C-1, to 1-O-acetyl-2,5-anhydro-3,4,6-tri-