Arabinitol, 2-0-methyl

Hydrogen bonding in polycrystalline ribitol, xylitol, D-arabinitol, methyl a-D-manno-, methyl a-D-gluco- and methyl p-D-galacto-pyranoside has been studied by IR spectroscopy at 20-300 °K. ... 

Deoxy arabinitol 5-Deoxy arabinitol Methyl 3-bromo-3-deoxy-arabino8ide Arabinose dithioacetal Lyxoee Derivatives Lyxoee... 

Pentitol synthesis An asymmetric synthesis of L-arabinitol involves condensation of the (E)-a,fJ-unsaturated ester (2) with the anion of methyl (R)-p-tolyl sulfoxide (1). The resulting p-keto sulfoxide (3) is reduced stereoselectively by ZnCl2/DIBAH (13, 115-116) to 4. Osmylation of 4 with (CH,)3NO and a catalytic amount of 0s04 (13, 224-225) yields essentially a single triol (5). Finally, a Pum-merer rearrangement of the sulfoxide followed by reduction of an intermediate... 

Galbis et al. described a variety of carbohydrate-based linear polyesters 61 of the poly(alkylene dicarboxylate) type that were obtained by polycondensation reactions of the alditols 2,3,4-tri-(9-methyl-L-arabinitol (9) and 2,3,4-tri-O-methyl-xylitol (10), and the aldaric acids 2,3,4-tri-(9-methyl-L-arabinaric acid (26) and 2,3,4-tri-(9-methyl-xylaric acid (27), butanediol, and adipic acid were also used as comonomers [28]. Copolyesters of the poly(aIkylene-c )-arylene dicarboxylate) type were obtained using bisphenols as comonomers (Scheme 1). Chemical polycondensation reactions were conducted in bulk or in solution. Enzymatic polycondensation reactions of adipic acid with the above-mentioned alditols were carried out successfully using Lipozyme and Novozyme 435. The hydrolytic degradations of some of these polyesters were also described. 

Copolyurethanes based on L-arabinitol and 2,2 -dithiodiethanol have been obtained by polyaddition reaction of mixtures of 2,2 -dithiodiethanol (DiT) and 2,3,4-tri-O-methyl-L-arabinitol (9) or 2,3,4-tri-O-benzyl-L-arabinitol (11) to 1,6 hexamethylene diisocyanate (HDI) [118]. 

S Omura, El Tomoda, N Tabata, Y Ohyama, A Abe, M Namikoshi. Roselipins, novel fungal metabolites having a highly methylated fatty acid modified with a mannose and an arabinitol. J Antibiot 52 586-589, 1999. 

Both 2,5-anhydro-D-mannitol and 2,5-anhydro-D-glucitol contain the requisite 1,4-anhydro-D-arabinitol ring system.215-240 The D-mannitol derivative is about 3.5 times as potent an inhibitor as the D-glucitol derivative, perhaps by virtue of the fact that it may bind to con A either through the hydroxyl groups at C-l, C-3, and C-4, or C-3, C-4, and C-6 (compare Ref. 429). Finally, the important observation that methyl a-and /3-D-fructofuranoside are inhibitors (the (3 anomer being approximately three times as active as the a anomer) provides an explanation for the interaction of con A with plant and bacterial levans120-215-364 (see Section II,l,h). 

Hung, R R, Straub, J A, Whitesides, G M, a-Amino aldehyde equivalents as substrates for rabbit muscle aldolase s3mthesis of l,4-dideoxy-l,4-imino-D-arabinitol and 2(R),5(R)-bis(hydroxy-methyl)-3(R),4(R)-dihydrox3fpyrrolidine, J. Org. Chem., 56, 3849-3855, 1991. 

Enders and Jegelka [88] have used l,3-dioxan-5-one 122, a protected dihydroxyacetone derivative, to construct enantiomerically pure C5- to C9-deoxycarbohydrates. For example, reaction of 122 with SAMP gives the hydrazone 123, which is deprotonated and alkylated with methyl iodide to yield 124. The monoalkylated hydrazone is then alkylated in the same manner with chloromethyl benzyl ether to form 125. Cleavage of the hydrazone with ozone furnishes the protected ulose 126 (>98% de, >98% ee), which is deprotected to (—)-5-deoxy-L-r/ir o-3-pentulose 127. Reduction of 126 with L-Selectride, followed by deprotection, provides 5-deoxy-D-arabinitol 128 (>95% de, >95% ee) (Scheme 13.46). 

Amyloses, 273, 283, 306, 310, 340, 341 Aniline, p-bromo-, 112 Anthranilic acid, 155 Arabinitol, 2-amino-2-deoxy-n-, 60 Arabinonic acid, 2,3,5-tri-O-methyl-D-, amide, 195... 

In a reaction that resembles the work of Gray and coworkers described above, Hughes and Speakman noted a 1—>4 migration of a methoxyl group in the reaction of the dimethyl acetal (22) with tetrabutylam-monium benzoate in iV-methylpyrrolidinone. The immediate product was the 4-0-methyl-ii-lyxose hemiacetal benzoate (24), which could be converted into the known 2-0-methyl-L-arabinitol (4-0-methyl-L-lyxitol)... 

Synthesis from i-arabinose Synthesis of l,4-dideoxy-l,4-imino-L-arabinitol (2) from methyl 3-L-arabinopyranoside has been reported (Scheme 4). The double inversion involving the introduction of the azide function at CA has been effected in... 

Synthesis from a-xylose The synthesis of 1,4-dideoxy-1,4-imino-L-arabinitol (2) can also be achieved from D-xylose (Scheme Thns, methyl (3-D-xylopyranoside (22) has... 

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