301523-39-7

Upstream product

• 38838-06-1 methyl 5-deoxy-5-iodo-2,3-isopropylidene-β-D-ribofuranoside 
• 106-95-6 allyl bromide 
• 100-46-9 benzylamine 
• 444883-29-8 (4S,6S)-6-[(triethylsilyl)oxy]-7-octen-1-yn-4-ol 
• 948056-06-2 N-(4S,5R)-benzyl-((2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)methylene)amine 
• 155934-55-7 (4R,5R)-2,2-dimethyl-5-vinyl-[1,3]dioxolane-4-carbaldehyde 
• 444883-30-1 (4S,5S,6R)-4-[(N-benzyl)amino]-5,6-(isopropylidenedioxy)-7-octen-1-yne 

Downstream Products

• 483341-78-2 (3R,4S,5S)-3,4-O-isopropylidene-5-(N-benzyl)-o-nitro-benzensulfon-amino-octa-1,7-diene-3,4-diol 
• 688334-35-2 (1S,2R,6S)-6-(N-benzyl)-o-nitrobenzenesulfonamino-cyclohex-3-ene-1,2-diol 
• 483341-80-6 (1S,2R,6S)-6-(N-benzyl)-o-nitrobenzenesulfonamino-1,2-di-O-carbonyl-cyclohex-3-ene-1,2-diol 
• 483341-79-3 (1S,2R,6S)-6-(N-benzyl)-o-nitrobenzenesulfonamino-1,2-O-isopropylidene-cyclohex-3-en-1,2-diol 
• 483341-81-7 (1R,4R,6S)-4,6-bis[(N-benzyl)-o-nitrobenzenesulfon-amino]-cyclohex-2-enol 

Relevant academic research and scientific papers

Carbohydrate carbocyclization by a zinc-mediated tandem reaction and ring-closing enyne metathesis

Methyl 5-deoxy-5-iodo-pentofuranosides are reductively ring-opened and propargylated in a tandem fashion in the presence of zinc. The 1,7-enynes thus obtained are subjected to ring-closing enyne metathesis with catalyst B to produce functionalized 1-vinyl cyclohexenes. By adding BnNH2 to the tandem reaction, an amino group can be introduced in the 1,7-enyne products. Addition of 2-TMS-ethynylcerium(III) chloride after the reductive ring-opening produces the corresponding 1,6-enynes. Further annulation of the product 1,3-dienes can be achieved through a Diels - Alder reaction with good control of stereochemistry. These procedures constitute efficient methods for rapid carbocyclization and annulation of carbohydrates to produce a variety of functionalized five- and six-membered ring systems.

A stereoselective route towards highly functionalized 4,6-diaminocyclohexene derivatives

A flexible synthetic route towards chirally pure 4,6-diaminocyclohexene derivatives based on palladium catalyzed allylic amination of carbohydrate derived cyclohexenes is presented.

Carbohydrate carbocyclization by a novel zinc-mediated domino reaction and ring-closing olefin metathesis

A general method for carbocyclization of carbohydrates is described using two consecutive organometallic transformations: a novel zinc-mediated domino reaction to give functionalized dienes followed by ring-closing olefin metathesis. In the first reaction

Zinc-mediated domino elimination-alkylation of methyl 5-iodopentofuranosides: An easy route to unsaturated carbohydrates for transition metal-catalyzed carbocyclizations

5-Iodopentofuranosides are converted with zinc and allyl/propargyl bromide into dienes/enynes which are further used in carbohydrate annulation reactions.