18390-72-2

Upstream product

• 13143-95-8 methyl 4-azido-2,3-di-O-benzoyl-4-deoxy-β-L-arabinopyranoside 
• 118117-09-2 methyl 4-azido-4-deoxy-2,3-O-isopropylidene-α-L-arabinopyranoside 
• 25029-43-0 methyl 4-O-p-nitrobenzenesulfonyl-β-D-xylopyranoside 
• 80245-11-0 methyl 2,3-di-O-benzoyl-α-D-xylopyranoside 
• 222973-58-2 methyl 2,3-di-O-benzoyl-β-L-arabinopyranozide 
• 83158-23-0 methyl 2,3-di-O-benzoyl-4-O-p-toluenesulfonyl-α-D-xylopyranoside 
• 101242-41-5 methyl 2,3-di-O-benzoyl-4-O-trifluoromethylsulfonyl-α-L-arabinopyranoside 
• 18930-05-7 methyl 2,3-di-O-benzoyl-4-bromo-4-deoxy-D-xylopyranoside 
• 612-05-5 methyl-β-D-xylopyranoside 
• 118117-08-1 methyl 2,3-O-isopropylidene-4-O-trifluoromethylsulfonyl-β-D-xylopyranoside 
• 118203-99-9 methyl 2,3-O-isopropylidene-β-D-xylopyranoside 

Downstream Products

• 96016-77-2 4-azido-2,3-di-O-benzyl-4-deoxy-β-L-arabinopyranose 
• 96022-39-8 methyl 4-azido-2,3-di-O-benzyl-4-deoxy-α-L-arabinopyranoside 
• 52019-89-3 (2S,3S,4S)-2-(hydroxymethyl)pyrrolidine-3,4-diol 

Relevant academic research and scientific papers

Efficient synthesis of 4-amino-4-deoxy-L-arabinose and spacer-equipped 4-amino-4-deoxy-L-arabinopyranosides by transglycosylation reactions

Methyl 4-azido-4-deoxy-l-arabinopyranoside has been synthesized in five steps starting from methyl-d-xylopyranoside in a multigram scale without chromatographic purification in 78% overall yield. The transformation relied on selective tosylation/nosylatio

Synthesis of and evaluation of lipid A modification by 4-substituted 4-deoxy arabinose analogs as potential inhibitors of bacterial polymyxin resistance

Three sets of novel 4-deoxy-l-arabinose analogs were synthesized and evaluated as potential inhibitors of the bacterial resistance mechanism in which lipid A, on the outer membrane, is modified with 4-amino-4-deoxy-l-arabinose (l-Ara4N). One compound diminished the transfer of l-Ara4N onto lipid A. These results suggest that small molecules might be designed that would effect the same reversal of bacterial resistance observed in genetic knockouts.

A CONVENIENT SYNTHESIS OF 4-AMINO-4-DEOXY-L-ARABINOSE AND ITS REDUCTION PRODUCT, 1,4-DIDEOXY-1,4-IMINO-L-ARABINITOL

Methyl β-D-xylopyranoside in a mixture of N,N-dimethylformamide and 2-methoxypropene containing a little hydrogen chloride gave preponderantly the 2,3-O-isopropylidene derivative, which was readily converted into its 4-trifluoromethanesulfonate.The facile displacement of the triflate group gave a 4-azido-4-deoxy-α-L-arabinopyranoside derivative, and this, on mild acid treatment, was hydrolyzed to the 2,3-diol, or under more vigorous conditions to 4-azido-4-deoxy-L-arabinose.Methyl 2,3-di-O-acetyl-4-azido-4-deoxy-α-L-arabinopyranoside, from the diol, appears (1H-n.m.r. data) to exist as an equilibrating mixture of the 4C1 and 1C4 conformers in chloroform solution.The reduction of the azido sugar by hydrogen over Pd/C in 6M HCl yielded 4-amino-4-deoxy-L-arabinose as its hydrochloride; in 0.1M HCl, further reactions occurred to give 1,4-dideoxy-1,4-imino-L-arabinitol as the final product.The aminodeoxypentose from lipid A precursor IIA, isolated from a Salmonella mutant by Raetz et al. in 1985, was shown to be identical with the synthetic aminoarabinose by t.l.c., 1H-n.m.r. spectroscopy, and g.l.c. of the acetylated reduction products.

IDENTIFICATION OF THE 2-HYDROXYMETHYL-3,4-DIHYDROXYPYRROLIDINE (OR 1,4-DIDEOXY-1,4-IMINOPENTITOL) FROM ANGYLOCALYX BOUTIQUEANUS AND FROM ARACHNIODES STANDISHII AS THE (2R, 3R, 4S)-ISOMER BY THE SYNTHESIS OF ITS ENANTIOMER.

The D-xylo and L-arabino isomers of 1,4-dideoxy-1,4-iminopentitol have been synthesised from L-arabinose, and the L-arabino isomer was found to be the enantiomer of the alkaloid from Angylocalyx Boutiqueanus.The alkaloid from Arachniodes Standishii, recently reported to have the xylo configuration, was also shown to be the D-arabino isomer.