201603-46-5

Upstream product

• 21204-67-1 methyl (triphenylphosphoranylidene)acetate 
• 195873-64-4 3,4,5-tri-O-benzyl-1,2-dideoxy-D-xylohept-1-enitol 
• 201603-52-3 tert-Butyl-dimethyl-((2R,3S,4R)-2,3,4-tris-benzyloxy-5,5-bis-ethylsulfanyl-pentyloxy)-silane 
• 215303-21-2 (2S,3S,4S,5S,6R)-4,5,6-Tris-benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-2,3-dihydroxy-heptanoic acid methyl ester 
• 100-39-0 benzyl bromide 
• 13263-74-6 D-xylose diethyl dithioacetal 
• 18039-26-4 2,3,4-tri-O-benzyl-D-xylopyranose 
• 91-09-8 methyl xyloside 
• 87-72-9 D-Xylose 
• 195873-65-5 (2S,3R,4S)-2,3,4-Tris-benzyloxy-hex-5-enal 
• 215303-20-1 (E)-(4S,5R,6R)-4,5,6-Tris-benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-hept-2-enoic acid methyl ester 
• 201603-43-2 tert-Butyl-dimethyl-((2R,3R,4S)-2,3,4-tris-benzyloxy-hex-5-enyloxy)-silane 
• 201603-40-9 (2R,3S,4R)-5-(tert-Butyl-dimethyl-silanyloxy)-1,1-bis-ethylsulfanyl-pentane-2,3,4-triol 
• 185987-56-8 2-(R)-3-(S)-4-(R)-tribenzyloxy-5-t-butyldimethylsilyloxy-pentanal 

Downstream Products

• 674325-82-7 methyl (3S,4R,5R,6S)-3-(4-methoxybenzo[d][1,3]dioxol-6-yl)-4,5,6-tri(benzyloxy)-7-octenoate 
• 906098-24-6 methyl (3S,4R,5R,6S)-3-(3,4-dimethoxyphenyl)-4,5,6-tri(benzyloxy)-7-octenoate 
• 906098-25-7 methyl (3S,4R,5R,6S)-3-(4-fluorophenyl)-4,5,6-tri(benzyloxy)-7-octenoate 
• 906098-23-5 (1R,2R,3S,6R)-6-(4-methoxybenzo[d][1,3]dioxol-6-yl)-4-cyclohexene-1,2,3-triol 
• 906098-33-7 4-((1S,4S,5R,6R)-4,5,6-tri(benzyloxy)cyclohex-2-enyl)-1,2-dimethoxybenzene 
• 906098-31-5 1-((3S,4R,5R,6S)-4,5,6-tri(benzyloxy)octa-1,7-dien-3-yl)-4-fluorobenzene 
• 906098-32-6 1-((3S,4R,5R,6S)-4,5,6-tri(benzyloxy)octa-1,7-dien-3-yl)-4-chlorobenzene 
• 906098-29-1 (3S,4R,5R,6S)-3-(4-chlorophenyl)-4,5,6-tri(benzyloxy)-7-octen-1-ol 

Relevant academic research and scientific papers

Synthesis and biological evaluation of aromatic analogues of conduritol F, L-chiro-inositol, and dihydroconduritol F structurally related to the amaryllidaceae anticancer constituents

Pancratistatin is a potent anticancer natural product, whose clinical evaluation is hampered by the limited natural abundance and the stereochemically complex structure undermining practical chemical preparation. Fifteen aromatic analogues of conduritol F, L-chiro-inositol, and dihydroconduritol F that possess four of the six pancratistatin stereocenters have been synthesized and evaluated for anticancer activity. These compounds serve as truncated pancratistatin analogues lacking the lactam ring B, but retaining the crucial C10a-C10b bond with the correct stereochemistry. The lack of activity of these compounds provides further insight into pancratistatin's minimum structural requirements for cytotoxicity, particularly the criticality of the intact phenanthridone skeleton. Significantly, these series provide rare examples of simple aromatic conduritol and inositol analogues and, therefore, this study expands the chemistry and biology of these important classes of compounds.

An approach to pancratistatins via ring-closing metathesis: Efficient synthesis of novel 1-aryl-1-deoxyconduritols F

Structurally novel cyclitols, 1-aryl-1-deoxyconduritols F, were efficiently prepared from D-xylose, utilizing RCM as a key step. Various aromatic residues were incorporated in the cyclitol skeleton with total stereochemical control, utilizing a diastereoselective aryl cuprate addition to a γ-alkoxy enoate. The synthetic route establishes a firm foundation for a practical synthesis of the antitumor alkaloid pancratistatin and its aryl analogues.

Free Radical Studies and Solutions to the Synthesis of (+)-Cyclophellitol

D-Xylose serves as a starting material for approaches to the synthesis of the glucosidase inhibitors, (+)-cyclophellitol (1) and (+)-epi-cyclophellitol (2). An investigation of the cyclization of diastereomeric oxiranyl radicals to achieve this goal was m