3254-32-8

Upstream product

• 98-88-4 benzoyl chloride 
• 18549-40-1 1,2-O-isopropylidene-α-D-glucofuranose 
• 14927-09-4 O¹,O²-isopropylidene-O³,O⁵-phenylboranediyl-α-D-glucofuranose 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 37614-73-6 1,2-O-isopropylidene-α-D-glucofuranose 3-O-benzoate 
• 81712-63-2 Benzoic acid (R)-2-benzhydryloxy-2-((3aR,5R,6S,6aR)-6-benzhydryloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethyl ester 
• 13964-22-2 3-O-benzoyl-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 65-85-0 benzoic acid 
• 15354-69-5 5,6-anhydro-1,2-O-isopropylidene-α-D-glucofuranose 
• 23397-77-5 endo/exo-5,6-O-Benzylidene-1,2-O-isopropylidene-α-D-glucofuranose 
• 623-11-0 1-methyl-4-nitrosobenzene 

Downstream Products

• 1003600-48-3 2,3-dideoxy-D-arabino-hept-2-enoic acid δ-lactone 4,6-diacetate 7-benzoate 
• 124572-55-0 (1R)-O²-acetyl-O³,O⁶-dibenzoyl-1-(6-benzoylamino-purin-9-yl)-D-xylo-1,4-anhydro-5-deoxy-hexitol 
• 51785-67-2 3,6-di-O-benzoyl-1,2-O-isopropylidene-5-deoxy-α-D-xylo-hexofuranose 
• 7057-09-2 1,2-O-isopropylidene-5-deoxy-α-D-glucofuranose 
• 78841-73-3 methyl 3-O-benzoyl-5-O-benzyl-6-deoxy-β-L-idofuranoside 
• 78841-72-2 methyl 3-O-benzoyl-5-O-benzyl-6-deoxy-α-L-idofuranoside 
• 78841-70-0 5-O-benzyl-6-deoxy-1,2-O-isopropylidene-β-L-idofuranose 
• 78841-76-6 methyl 5-O-benzyl-2,6-dideoxy-α-L-lyxo-hexofuranoside 
• 78841-75-5 methyl 2,3-anhydro-5-O-benzyl-α-L-gulofuranoside 
• 78841-74-4 methyl 3-O-benzoyl-5-O-benzyl-6-deoxy-2-O-p-tolylsulfonyl-α-L-idofuranoside 
• 78841-69-7 5-O-benzyl-6-deoxy-1,2-O-isopropylidene-3-(2-phenethylsulfonyl)-β-L-idofuranose 
• 78841-71-1 3-O-benzoyl-5-O-benzyl-6-deoxy-1,2-O-isopropylidene-β-L-idofuranose 
• 78841-68-6 5-O-benzyl-6-deoxy-1,2-O-isopropylidene-3-O-(methylsulfonyl)-β-L-idofuranose 
• 78841-77-7 methyl 5-O-benzyl-2,6-dideoxy-3-O-(methylsulfonyl)-α-L-lyxo-hexofuranoside 

Relevant academic research and scientific papers

Boronic esters as protective groups in carbohydrate chemistry: processes for acylation, silylation and alkylation of glycoside-derived boronates

Procedures for selective installation of acyl, silyl ether and para-methoxybenzyl (PMB) ether groups to glycoside substrates have been developed, employing phenylboronic esters as protected intermediates. The sequence of boronic ester formation, functiona

New antitumour agents with α,β-unsaturated δ-lactone scaffold: Synthesis and antiproliferative activity of (?)-cleistenolide and analogues

A stereoselective total synthesis of (?)-cleistenolide (1) from D-glucose has been achieved. This new approach for the synthesis of (?)-cleistenolide and analogues involves a one-C-atom degradation of the chiral precursor, (Z)-selective Wittig olefination, followed by the final δ-lactonisation. Synthesized compounds showed potent growth inhibitory effects against selected human tumour cell lines, especially 2,4,6-trichlorobenzoyl derivative 12, which in the culture of MDA-MB 231 cells displayed the highest activity (IC500.02?μM) of all compounds under evaluation. A preliminary SAR study reveals the structural features that are beneficial for antiproliferative activity of synthesized δ-lactones, such as presence of either electron-withdrawing or electron-donating substituents in the aromatic ring, as well as the presence of cinnamoyl functionality instead of benzoyl group at the O-7 position.

A concise total synthesis of cleistenolide

A concise total synthesis of cleistenolide has been achieved from D-glucose. The synthesis of cleistenolide proceeds in six steps from D-glucose diacetonide in 42.5% overall yield. Selective benzoylation and Still-Gennari olefination are the key reactions involved in the synthesis.

Modifying the regioselectivity of glycosynthase reactions through changes in the acceptor

Successful glycosynthase-mediated reactions have been performed on 6-O-benzyl-, 6-O-(4-nitrobenzyl)-, and 6-O-benzoyl-D-glucopyranose to give 1,2-β- and 1,3-β-D-glycosylated products; 4-O-benzyl-D-xylopyranose gave only a 1,2-β-glycosylated product. A rat

Control of regioselectivity in reactions of dialkylstannylene acetals. Part I. A dramatic reversal of regioselectivity in mono-p-toluenesulfonation reactions

The regioselectivities of p-toluenesulfonation reactions of dialkylstannylene acetals obtained from a number of carbohydrate-derived terminal 1,2-diols in the absence of added nucleophiles have been explored as functions of the carbohydrate structure, the

Regioselective monotosylation of non-protected and partially protected glycosides by the dibutyltin oxide method

Tosylation of non-protected glycopyranosides with p-toluenesulfonyl chloride in the presence of 4-dimethylaminopyridine, after activiation of the glycosides by dibutyltin oxide, gave mono-O-tosylates in good yield. The regioselectivity in this tosylation

DIPHENYLMETHYLATION OF CARBOHYDRATE HYDROXYL GROUPS BY THE REACTION WITH DIAZO(DIPHENYL)METHANE

Diphenylmetylation of carbohydrate hydroxyl groups may be effected by the thermal reaction with diazo(diphenyl)methane in absence of catalysts.Migration of the labile ester groups of methyl 2,3,4-tri-O-acetyl-α-D-glucopyranoside and 3-O-benzoyl-1,2-O-isopropylidene-α-D-glucofuranose does not occur during diphenylmethylation by this procedure.The diphenylmethyl group may be readily removed by catalytic hydrogenolysis, and is sufficiently acid-stable to enable the selective hydrolysis of acetal groups.Its use as an O-4 protecting-group and as a non-participating O-2 protecting-group in α-glucoside synthesis has been demonstrated in syntheses of methyl 2,3,6-tri-O-methyl-α-D-glucopyranoside and kojibiose octa-acetate, respectively.

A Simple Regioselective Partial Hydrolysis of Di-O-isopropylidene Monosaccharides with Copper(II) Ion

Copper(II) ion was found to be effective for regioselective removal of the 5,6-O-isopropylidene group of α-D-mannose and α-D-glucose derivatives in alcohols at ambient temperature.