193271-77-1

Upstream product

• 97-30-3 methyl-alpha-D-glucopyranoside 
• 3162-96-7 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 
• 3150-15-0 methyl 2,3-anhydro-4,6-O-benzilidene-α-D-mannopyranoside 
• 163580-26-5 methyl 4,6-O-benzylidene-3-C-cyano-3-deoxy-α-D-altropyranoside 
• 272113-74-3 methyl 4,6-O-benzylidine-3-C-cyano-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 542-92-7 cyclopenta-1,3-diene 
• 193271-74-8 methyl 4,6-O-benzylidene-2,3-dideoxy-3-C-formyl-α-D-erythro-hex-2-enopyranoside 

Downstream Products

• 193271-84-0 (1S,2S,3S,5R,8R,10S,11S,12R)-10-methoxy-5-phenyl-4,6,9-trioxatetracyclo[10.2.1.0^2,11.0^3,8]pentadec-13-ene-2-carboxylic acid methyl ester 
• 201025-01-6 (1S,2S,3S,5R,8R,10S,11S,12R)-10-methoxy-5-phenyl-2-(1-oxopropyl)-4,6,9-trioxatetracyclo[10.2.1.0^2,11.0^3,8]pentadec-13-ene 
• 910324-27-5 (1S,2S,4S,4aS,5R,6aS,9aS)-1-Benzoyloxy-2-iodomethyl-4-methoxy-8-methyl-7-oxo-1,2,4,4a,5,6,6a,7-octahydro-pentaleno[1,6a-c]pyran-5-carboxylic acid methyl ester 
• 910324-26-4 (1S,2S,4S,4aS,5R,6aS,9aS)-1-Benzoyloxy-2-bromomethyl-4-methoxy-8-methyl-7-oxo-1,2,4,4a,5,6,6a,7-octahydro-pentaleno[1,6a-c]pyran-5-carboxylic acid methyl ester 
• 910324-24-2 (2R,4aR,6S,6aS,7S,9R,9aR,9bS)-9a-Formyl-6-methoxy-2-phenyl-9-propionyl-octahydro-cyclopenta[4,5]pyrano[3,2-d][1,3]dioxine-7-carboxylic acid 
• 910324-28-6 (1S,4S,4aS,5R,6aS,9aS)-1-Benzoyloxy-4-methoxy-8-methyl-2-methylene-7-oxo-1,2,4,4a,5,6,6a,7-octahydro-pentaleno[1,6a-c]pyran-5-carboxylic acid methyl ester 
• 910324-29-7 (1S,4S,4aS,5R,6aS,9aS)-1-Benzoyloxy-4-methoxy-8-methyl-2,7-dioxo-1,2,4,4a,5,6,6a,7-octahydro-pentaleno[1,6a-c]pyran-5-carboxylic acid methyl ester 
• 910324-25-3 (2R,2aS,3S,4aR,7R,8aS,8bS,11aS)-3-Methoxy-10-methyl-11-oxo-7-phenyl-1,2,2a,3,4a,8a,11,11a-octahydro-5H-4,6,8-trioxa-pentaleno[6a,1-a]naphthalene-2-carboxylic acid methyl ester 
• 959842-59-2 (1S,2R,3S,5R,8R,10S,11S,12R)-2-(hydroxymethyl)-10-methoxy-5-phenyl-4,6,9-trioxatetracyclo[10.2.1.0^2,11.0^3,8]pentadec-13-ene 
• 676451-02-8 (1S,2S,4R,7R,9S,10S,11S,13R)-1,13-dicarbaldehyde-9-methoxy-4-phenyl-3,5,8-trioxatricyclo[8.3.0^1,10.0^2.7]tridecane-11-carboxylic acid methyl ester 
• 193271-80-6 C₂₀H₂₂O₆ 

Relevant academic research and scientific papers

Experimental and theoretical study of a Diels-Alder reaction between a sugar-derived nitroalkene and cyclopentadiene

The Diels-Alder reaction of a pyranose-derived nitroalkene 1 with cyclopentadiene is described, and the unexpected facial selectivity of the cycloaddition is analyzed by a computational study.

Enantiospecific approach toward pentalenolactone

The enantiospecific assembly of the pentalenolactones' carbon skeleton was achieved in 17 steps and 16% overall yield from methyl α-D- glucopyranoside. The synthetic strategy relies on two highly efficient key steps: an exo-diastereoselective Diels Alder

Diels-Alder reaction of sugar-derived cyclic dienophiles with cyclopentadiene. Factors affecting the reactivity and stereoselectivity

A sugar-derived cyclic dienophile showed a high exo and face selectivity in the Diels-Alder reaction with cyclopentadiene. Structural modifications on the dienophile structure were made, and the outcomes of the cycloaddition reactions were investigated. T

Efficient enantiospecific entry to a highly functionalized cyclopentane building block

A simple and efficient route has been developed for the synthesis of a polyfunctionalized cyclopentane in enantiomerically pure form. D-Glucose is the source of chirality for this versatile building block and a highly diastereoselective Diels-Alder reaction with cyclopentadiene is the key step.

Enantiospecific approach to a quinane skeleton related to pentalenolactones

A novel and general approach has been delineated for the enantiomerically pure synthesis of the angularly fused tricyclic system of the pentalenolactone family of compounds. D-Glucose is used as starting material and a diasteroselective Diels-Alder reaction sets the elements for the ring junctions.