195873-64-4

Upstream product

• 18039-26-4 2,3,4-tri-O-benzyl-D-xylopyranose 
• 19493-09-5 Methylenetriphenylphosphorane 
• 100-39-0 benzyl bromide 
• 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 
• 13263-74-6 D-xylose diethyl dithioacetal 
• 87-72-9 D-Xylose 
• 201603-43-2 tert-Butyl-dimethyl-((2R,3R,4S)-2,3,4-tris-benzyloxy-hex-5-enyloxy)-silane 
• 185987-56-8 2-(R)-3-(S)-4-(R)-tribenzyloxy-5-t-butyldimethylsilyloxy-pentanal 
• 91-09-8 methyl xyloside 
• 215303-20-1 (E)-(4S,5R,6R)-4,5,6-Tris-benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-hept-2-enoic acid methyl ester 
• 201603-52-3 tert-Butyl-dimethyl-((2R,3S,4R)-2,3,4-tris-benzyloxy-5,5-bis-ethylsulfanyl-pentyloxy)-silane 
• 201603-40-9 (2R,3S,4R)-5-(tert-Butyl-dimethyl-silanyloxy)-1,1-bis-ethylsulfanyl-pentane-2,3,4-triol 

Downstream Products

• 201603-46-5 methyl (2E,4R,5R,6S)-4,5,6-tri(benzyloxy)-2,7-octadienoate 
• 592497-04-6 3,4,5-tri-O-benzyl-1,2-dideoxy-6-O-vinyl-D-xylohept-1-ene 
• 592497-12-6 1,6-anhydro-3,4,5-tri-O-benzyl-2-deoxy-D-xylo-hept-1-enitol 
• 697766-92-0 1,2-anhydro-3,4,5-tri-O-benzyl-2-deoxy-β-D-idoseptanose 
• 697766-93-1 methyl 3,4,5-tri-O-benzyl-α-D-idoseptanoside 
• 697767-02-5 phenyl 3,4,5-tri-O-benzyl-1-thio-α-D-idoseptanoside 
• 157761-58-5 ((1R,2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-7-oxabicyclo-[4.1.0]heptan-2-yl)methanol (+)-2,3,4-tri-O-benzylcyclophellitol 
• 201603-61-4 (1R,2R,3R,4S,5R,6S)-4,5-bis(benzyloxy)-2-(hydroxymethyl)-7-oxabicyclo[4.1.0]heptan-3-ol 
• 201603-59-0 (1R,2R,3S,4R,5R,6R)-2,3,4-Tris-benzyloxy-5-iodomethyl-7-oxa-bicyclo[4.1.0]heptane 
• 201603-57-8 (3aR,4R,5S,6R,7S,7aR)-4,5,6-Tris-benzyloxy-7-iodo-octahydro-benzofuran-2-ol 
• 201603-58-9 Formic acid (1R,2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-2-iodo-6-iodomethyl-cyclohexyl ester 
• 201603-54-5 (3aR,4R,5S,6R,7S,7aR)-4,5,6-Tris-benzyloxy-7-iodo-hexahydro-benzofuran-2-one 
• 201603-50-1 ((1S,4S,5R,6R)-4,5,6-Tris-benzyloxy-cyclohex-2-enyl)-acetic acid methyl ester 
• 201603-48-7 (3S,4R,5R,6S)-4,5,6-Tris-benzyloxy-3-vinyl-oct-7-enoic acid methyl ester 

Relevant academic research and scientific papers

Straightforward synthesis of diverse 1-deoxyazapyranosides via stereocontrolled nucleophilic additions to six-membered cyclic nitrones

A systematic study of diastereoselective nucleophilic addition of Grignard reagents to six-membered chiral tri-O-benzyl cyclic nitrones is described. With all eight chiral cyclic nitrones and asymmetric reaction conditions in hand, a practical methodology is established for the preparation of diverse 1-deoxyazapyranosides bearing various stereogenic centers. We have developed practical methods to prepare all eight six-membered chiral cyclic nitrones. Using these cyclic nitrones and diastereoselective nucleophilic additions, 12 examples of diverse 1-deoxyazapyranosides including enantiomers were synthesized to demonstrate the generality and flexibility of this new approach.

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.

Synthesis, crystal structure, and reactivity of a D-xylose based oxepine

The synthesis and X-ray crystal structure of a D-xylose-based oxepine (9) are reported. The oxepine was prepared from 2,3,4-tri-O-benzyl-D-xylose by the three-step sequence (Wittig olefination, vinyl ether formation, and ring closing metathesis) we recently reported. Epoxidation of this cyclic enol ether (9) using dimethyldioxirane (DMDO) gave 1,2-anhydro-β-D-idoseptanose (10), which was trapped by a number of nucleophiles to give α-idoseptanosides. The stereochemistry of epoxidation was assigned based on product analysis. Spectroscopic data of methyl 2,3,4,5-tetra-O-acetyl-α-D-idoseptanoside, derived from the methanolysis product 11, was compared to data of its enantiomer, the known methyl 2,3,4,5-tetra-O-acetyl-α-L-idoseptanoside.

Carbohydrate-based oxepines: Ring expanded glycals for the synthesis of septanose saccharides

A ring-closing metathesis (RCM) approach to a family of carbohydrate-based oxepines is described. A variety of readily accessible, protected monosaccharide derived dienes were used to demonstrate the utility of the synthetic sequence and to investigate ho

Synthesis of cyclitols via ring-closing metathesis

A convenient synthesis of enantiomerically pure and differentially protected L-chiro- and myo-inositols as well as conduritols B and F from 2,3,4-tri-O-benzyl-D-xylopyranose via ring-closing metathesis is reported. The facile synthesis of conduritol B con

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

Enantiospecific synthesis of a differentially protected L-chiro-inositol from D-xylose

A convenient synthesis of differentially protected L-chiro-inositol 7 from 2,3,4-tri-O-benzyl-D-xylopyranose is described The structure of 7 was confirmed by its transformation to the pentabenzylated derivative of(-)quebrachitol.