18439-35-5

Upstream product

• 350255-13-9 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 100-58-3 phenylmagnesium bromide 
• 53167-11-6 1,2-O-isopropylidene-α-D-xylo-pentodialdo-1,4-furanose 
• 108-86-1 bromobenzene 
• 152185-56-3 3-O-Allyl-1,2-O-isopropylidene-α-D-xylo-pentodialdose 
• 70057-97-5 6-hydroxy-2,2-dimethyl-(3aR,5R,6S,6aR)-perhydrofuro[2,3-d][1,3]dioxole-5-carbaldehyde 
• 18685-18-2 3-O-benzyl-1,2-5,6-O-diisopropylidene-α-D-glucofuranose 
• 65462-15-9 3-O-benzyl-1,2-O-isopropylidene-β-L-arabino-pentodialdo-1,4-furanose 
• 18439-43-5 3-O-benzyl-1,2-O-isopropylidene-5-C-phenyl-α-D-gluco-pentafuranose 
• 18439-42-4 3-O-benzyl-1,2-O-isopropylidene-5-C-phenyl-α-L-ido-pentofuranose 
• 18439-34-4 (3aR,5R,6S,6aR)-5-((S)-hydroxy(phenyl)methyl)-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxole-6-ol 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 18549-40-1 1,2-O-isopropylidene-α-D-glucofuranose 

Downstream Products

• 136778-39-7 (+)-goniofufurone 
• 1233484-17-7 5-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-5-C-phenyl-α-D-gluco-pentofuranose 
• 1241404-75-0 (5R,SP)-1,2-O-isopropylidene-5-phenyl-3,5-O-(5'-(2',3'-O-isopropiliden-5-metyluridinyl))phosphoryl-α-D-xylofuranose 
• 1241404-76-1 (5R,RP)-1,2-O-isopropylidene-5-phenyl-3,5-O-(5'-(2',3'-O-isopropiliden-5-metyluridinyl))phosphoryl-α-D-xylofuranose 
• 1262487-78-4 (R)-((3aR,5R,6S,6aR)-6-(cinnamoyloxy)-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)(phenyl)methyl cinnamate 
• 1413282-41-3 C₁₂H₁₂O₆ 
• 918906-87-3 8-epi-crassalactone D 
• 1413282-39-9 3,5-O-carbonyl-1,2-O-isopropylidene-5-C-phenyl-α-D-glucopentofuranose 
• 1233484-11-1 5-O-(tert-butyldiphenylsilyl)-3-O-cinnamoyl-1,2-O-isopropylidene-5-C-phenyl-α-D-gluco-pentofuranose 
• 1262487-77-3 (R)-((3aR,5S,6S,6aR)-6-hydroxy-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)(phenyl)methyl cinnamate 
• 1190851-29-6 4-epi-(+)-crassalactone D 

Relevant academic research and scientific papers

On the nature of the electronic effect of multiple hydroxyl groups in the 6-membered ring-the effects are additive but steric hindrance plays a role too

Research during the last two decades has shown a remarkable directional component of the substituent effects of hydroxy groups, which has a profound effect on the properties of hydroxylated compounds such as carbohydrates. While the epimerisation of a single hydroxyl function is well studied the consequence of multiple epimerisations is more speculative. In this work the effect of three epimerisations was investigated. To this end epimeric 2-phenyl iminoxylitols that have a phenyl group as a conformational anchor and thus hydroxyl groups in the axial or equatorial position, respectively, were synthesized and their pKa and conformation were studied. The results show that the large difference in the electronic effect between the axial and equatorial hydroxyls is partially cancelled by counteracting steric hindrance from 1,3-diaxial interactions. Hydrogen bonding does not appear to play any role in the electronic influence of the hydroxyl groups.

Asymmetric synthesis and biological evaluation of (+)-cardiobutanolide, (?)-3-deoxycardiobutanolide and analogues as antiproliferative agents

Two natural products, (+)-cardiobutanolide and (?)-3-deoxycardiobutanolide, as well as five new analogues, were synthesized in several steps that included zinc-mediated THF ring opening, subsequent stereoselective olefination, and final Sharpless asymmetric dihydroxylation. In vitro antitumour activities of these compounds were evaluated against a panel of eight human tumour cell lines and one normal cell line. Some of compounds displayed powerful effects against tumour cells, but none of them were active toward normal cells. A SAR study revealed that the change of configuration at the C-6 and C-7 position of (+)-cardiobutanolide decreases antitumour activity of analogues. It also appears that the presence of a hydroxyl group at the C-3 position increases the activity of this type of lactones. A comparison of activities of conformationally rigid lactone goniofufurone with that of more flexible cardiobutanolide and 3-deoxycardiobutanolide indicates that steric flexibility has a positive effect on cytotoxicity. It was also confirmed that removal of the phenyl group may result in analogues of higher activity. Flow cytometry analysis revealed that the synthesized compounds did not induce apoptosis and necrosis of K562 cells. However, Western blot analysis showed that all compounds but one had an increased Bax/Bcl-2 protein expression ratio.

Divergent total synthesis of crassalactones B and C and evaluation of their antiproliferative activity

A divergent total synthesis of cytotoxic natural products (+)-crassalactones B (2) and C (3) has been achieved by utilizing diacetone d-glucose (4) as a chiral precursor. The key steps of the synthesis of both targets 2 and 3 were a stereo-selective addit

Conformationally constrained goniofufurone mimics as inhibitors of tumour cells growth: Design, synthesis and SAR study

Synthesis of conformationally restricted (+)-goniofufurone (1) and 7-epi-(+)-goniofufurone (2) analogues, with embedded O-isopropylidene, O-methylidene or cyclic carbonate functions is disclosed starting from d-glucose. A number of potential bioisosteres

Divergent synthesis of cytotoxic styryl lactones isolated from Polyalthia crassa. The first total synthesis of crassalactone B

The first total synthesis of (+)-crassalactone B (2) and a new syntheses of (+)-crassalactone C (3) has been achieved starting from d-glucose. The natural products 2 and 3 can be selectively accessed by changing the conditions for TBDPS cleavage in the fi

Stereoselective total synthesis of styryl-lactones: (+)-crassalactones B and C, (+)-howiionol A, (+)-tricinnamate, (+)-goniofufurone and (+)-dicinnamoyl goniofufurone

The total synthesis of (+)-crassalactone B, (+)-crassalactone C, (+)-howiionol A, (+)-tricinnamate, (+)-goniofufurone, and (+)-dicinnamoyl goniofufurone is achieved by a 'chiron approach' starting from diacetone d-glucose (DAG). Mitsunobu inversion, Wittig olefination and ring closing metatheses were used as key steps for (+)-howiionol A and (+)-tricinnamate. Meldrum's acid was used for the synthesis of (+)-crassalactone C, (+)-goniofufurone, and (+)-dicinnamoyl goniofufurone. Yamaguchi esterification was used for (+)-crassalactone B, while a Grignard reaction followed by concomitant deallylation was first reported in the synthesis of (+)-dicinnamoyl goniofufurone.

Six-membered ring phosphates and phosphonates as model compounds for cyclic phosphate prodrugs: Is the anomeric effect involved in the selective and spontaneous cleavage of cyclic phosphate prodrugs?

(Chemical Equation Presented) In recent years, several six-membered ring phosph(on)ates and phosphonamides have been reported as potent prodrugs against liver diseases such as hepatitis B and C and also as antitumor agents. Apparently, the success for the

Conformational analysis of cyclic phosphates derived from 5-C′ substituted 1,2-O-isopropylidene-α-D-xylofuranose derivatives

Twelve 2-phenoxy-2-oxo-1,3,2-dioxaphosphorinanes fused with a 1,2-O-isopropylidene-α-D-xylofuranose moiety in cis orientation and substituted at the C′5 position were prepared in two steps from commercially available diacetone-α-D-glucose. Their conformations, and configurations were determined by 1H and 31P NMR and X-ray crystallographic techniques. Both, chair-twisted-chair and chair-boat equilibria were observed in solution. We observed that the strong anisotropic shielding effect of the benzene ring in the phenoxy group generates an upfield shift of the H1 hydrogen atom, when the cyclic phosphates adopt a boat conformation. This is due to a relative cis-orientation of the P-phenoxy group and the H1 proton of the 1,2-O-isopropylidene-α-D-xylofuranose moiety. Therefore, the configuration of the phosphorus center (SP or RP) can be determined by 1H NMR spectroscopy. Interestingly, the crystal structure of one of the cyclic phosphates exhibits two independent molecules in the asymmetric unit, one with a chair and the other one with a boat conformation.

Application of the reaction of D-glucose with meldrum's acid: Total synthesis of the styryl lactones (+)-goniofufurone and (+)-7-epi- goniofufurone

The syntheses of the styryl lactones (+)-goniofufurone (1) and (+)-7- epi-goniofufurone (2) from D-glucose are presented. The key steps are the formation of the lactone moiety by reaction of the hemiacetals 15 and 16 with meldrum's acid (3) and the addition of phenylmagnesium bromide to the aldehydes 9 or 12. In the last case, we obtained the L-ido and D-gluco configurated products 13 and 14 in a 3:1 mixture. However, addition of ZnCl2 shifted the diastereomeric ratio towards the desired compound 14.