170872-96-5

Upstream product

• 1005-56-7 phenylcarbonochloridothioate 
• 3067-56-9 D-glucurono-3,6-lactone acetonide 
• 14362-29-9 α-D-glucurono-γ-lactone 

Downstream Products

• 170872-98-7 Methyl 1,2-O-isopropylidene-5-O-(phenoxythiocarbonyl)-α-D-glucuronate 
• 956317-01-4 3,6-anhydro-5-O-benzyl-2-deoxy-7-C-phenyl-D-glycero-D-ido-heptono-1,4-lactone 
• 136778-39-7 (+)-goniofufurone 
• 111651-70-8 (3aR,6R,6aS)-6-Benzyloxy-5-methoxy-tetrahydro-furo[3,2-b]furan-2-one 
• 170873-33-3 3-O-(tert-Butyldimethylsilyl)-10-chloro-5,7,10-trideoxy-6,8,11-tri-O-(triethylsilyl)-1,2-O-isopropylidene-9-O-(methoxymethyl)-7-C-<<(2-nitrophenyl)seleno>methyl>-α-D-gluco-L-ido-undecofuranose 
• 170873-39-9 3,6,10-Tri-O-acetyl-8,11-anhydro-5,7-dideoxy-O-1,2-isopropylidene-9-O-(methoxymethyl)-7-C-<<(2-nitrophenyl)seleno>methyl>-β-L-ido-L-ido-undecofuranose 
• 170873-38-8 (3aR,5R,6S,6aR)-5-[(2R,3S)-2-Hydroxy-3-((2R,3R,4S)-4-hydroxy-3-methoxymethoxy-tetrahydro-furan-2-yl)-4-(2-nitro-phenylselanyl)-butyl]-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol 
• 170873-34-4 10,11-Anhydro-5,7-dideoxy-1,2-O-isopropylidene-9-O-(methoxymethyl)-7-C-<<(2-nitrophenyl)seleno>methyl>-β-L-ido-L-ido-undecofuranose 
• 170872-99-8 Methyl 3-O-(tert-butyldimethylsilyl)-1,2-O-isopropylidene-5-O-(phenoxythiocarbonyl)-α-D-glucuronate 
• 879881-41-1 (4R,5S)-4-Benzyloxy-5-((1S,2R,3R)-1,2-bis-benzyloxy-3-hydroxy-3-phenyl-propyl)-dihydro-furan-2-one 

Relevant academic research and scientific papers

Stereospecific α-alkoxystannane couplings with acyl chlorides: Total synthesis of (+)-goniofufurone

Stereospecific C-glycoside formation via Pd/Cu mediated coupling of PhCOCl with cyclic α-alkoxystannane 6, derived from D-glucurono-6,3-lactone, was the key transformation in a concise total synthesis of the anticancer agent (+)-goniofufurone.

Novel and stereocontrolled asymmetric synthesis of a new naturally occurring styryllactone, (+)-cardiobutanolide

An efficient and stereodefined strategy is described for the asymmetric synthesis of a new styryllactone from the stem bark of Goniothalamus cardiopetalus, cardiobutanolide. The synthetic process is based on requisite manipulation of the functionalized bicyclic lactol-lactone intermediate incorporating the glucuronolactone-derived skeleton in a complete stereoselective manner.

Synthesis of Undeculofuranoside Derivatives of the Herbicidins and of Analogues

The condensation of 3-O-(tert-butyldimethylsilyl)-5-deoxy-1,2-O-isopropylidene-α-D-xylo-hexodialdo-1,4-furanose (obtained in six steps (35percent) from D-glucurono-6,3-lactone) with the lithium enolate of (+/-)-6-endo-chloro-5-endo-(methoxymethoxy)-7-oxabicycloheptan-2-one (derived in six steps (25percent) from the Diels-Alder adduct of furan to 1-cyanovinyl acetate) was highly exo face selective giving two major aldols that were separated readily.One of them was converted to 6,10-anhydro-5-deoxy-1,2-O-isopropylidene-9-O-(methoxymethyl)-α-D-arabino-L-ido-7-undeculofuranose-(1,4)-pyranose-(7,3), a semiprotected form of the long-chain carbohydrate moiety of the herbicidins.The synthesis implies the acid-promoted isomerization of 10,11-anhydro-5,7-dideoxy-1,2-O-isopropylidene-9-O-(methoxymethyl)-7-C--β-L-ido-L-ido-undecofuranose.