345341-14-2

Upstream product

• 61550-02-5 (furan-2-yloxy)-trimethylsilane 
• 81028-12-8 (4S,5R)-4-benzyloxymethyl-2,2-dimethyl-1,3-dioxolane-5-carboxaldehyde 
• 121896-38-6 2-tert-butyldimethylsilyloxyfuran 
• 77-76-9 2,2-dimethoxy-propane 
• 78469-77-9 (4S,5S)-4-benzyloxymethyl-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolane 
• 37031-29-1 (-)-dimethy-2,3-O-isopropylidene-L-tartrate 
• 50622-09-8 2,3-O-isopropylidene-L-threitol 

Downstream Products

• 583040-14-6 (R)-5-[(S)-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-dihydro-furan-2-one 
• 138584-55-1 1,2,3,4-tetra-O-acetyl-6,7-O-isopropylidene-8-O-benzyl-L-threo-D-talo-octopyranose 
• 138584-54-0 1,2,3,4-tetra-O-acetyl-6,7-O-isopropylidene-8-O-benzyl-L-threo-D-talo-octopyranose 
• 138584-53-9 2,3,5-tri-O-(trimethylsilyl)-6,7-O-isopropylidene-8-O-benzyl-L-threo-D-talo-octono-1,4-lactone 
• 138584-52-8 (3S,4R,5R)-5-[(R)-((4R,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-trimethylsilanyloxy-methyl]-3,4-dihydroxy-dihydro-furan-2-one 
• 583039-93-4 (1'S,4''R,5R,5''S)-5-[(5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-(tert-butyldimethylsilanyloxy)methyl]-3,4-dihydro-5H-furan-2-one 
• 138584-51-7 5-O-(trimethylsilyl)-6,7-O-isopropylidene-8-O-benzyl-2,3-dideoxy-L-galacto-oct-2-enono-1,4-lactone 

Relevant academic research and scientific papers

Variable strategy toward carbasugars and relatives. 5. Focus on preparation of chiral nonracemic medium-sized carbocycles

The feasibility of sequential vinylogous aldol (intermolecular)/silylative aldol (intramolecular) addition reactions involving furan- and pyrrole-based dienoxysilanes, 6 and 12, in the synthesis of carbasugar frameworks is illustrated by the preparation of the scantily investigated carbaseptanose and carbaoctanose representatives of this class of compounds. The target compounds, 1, 2, 3, ent-2, ent-3, and 4, were obtained from readily available carbohydrate precursors (5 and 19) in yields of 21-30% over 8-12 steps. The irreversible silylative ring-closing aldolisation of γ-substituted dihydro-5H-furan-2-one and pyrrolidin-2-one aldehydes (9, 16, ent- 16, and 22) driven by the TBSOTf/ Pri2EtN Lewis acid-Lewis base couple was shown to be a practical, diastereoselective maneuver to forge the densely functionalized, medium-sized core carbocycles.

Synthesis of carba sugars from aldonolactones. Part IV. Stereospecific synthesis of carbaheptopyranoses by radical-induced carbocyclisation of 2,3-unsaturated octonolactones

Three new carbaheptopyranoses, 6-deoxy-5a-carba-β-L-gulo- (8), 5a-carba-D-glycero-β-D-ido- (22) and 5a-carba-Lglycero-α-L-galacto-heptopyranose (25), have been prepared from 8-bromo-8-deoxy-2,3-unsaturated octono-1,4-lactones with L-galacto-, D-gluco- and D-manno-configuration, respectively. The key step was a regio- and stereoselective 6-exo-trig radical-induced carbocyclisation of the unsaturated octonolactones to give bicyclic cyclohexane-lactone derivatives. Reduction of the lactone moiety using Ca(BH4)2 gave the said carbaheptopyranoses. The 8-bromo-8-deoxy-2,3-unsaturated octonolactones were prepared from the inexpensive, commercially available D-glycero-D-gulo-heptonolactone and L-tartaric acid.

Highly stereoselective total synthesis of octopyranose derivatives

A couple of enantiomeric octopyranoses, endowed with differentiated protective groups, namely the L-threo-D-talo-and D-threo-L-talo- octose derivatives L-6 and D-6, were synthesized from the enantiomers of threose L-1 and D-1 in ca 10% overall yield in five individual steps. The synthetic plan emphasizes the value of 2-(trimethylsiloxy)furan (TMSOF) as four-carbon homologative reactant of homochiral aldehyde precursors en route to higher-carbon monosaccharide units.