Allopyranoside

In a second approach (see Figure 3) the alloside derivative 11 was converted, by mild acid hydrolysis, into methyl 2-O-toluene-p-sulfonyl a-D-allopyranoside (18). Acid catalyzed acetonation of compound 18... [Pg.70]

Our initial studies were directed towards the synthesis and characterization of phenylboronate esters derived from methyl 6-deoxy-/ -D-allopyranoside, methyl a-L-rhamnopyranoside, methyl -L-fucopyranoside, and methyl 6-deoxy-/ -D-glucopyranoside. Previous work (14) in this laboratory indicated that the reaction of triphenylboroxole and methyl... [Pg.73]

The Action of Alkali on Methyl 2 3-Anhydro-a-D-allopyranoside and l 5-Anhydro-2-deoxy-3-0-toluene-p-sulphonyl-D-arabino-hexitol," A. B. Foster, M. Stacey, and S. V. Vardheim, Acta Chem. Scand., 12(1958) 1819-1824. [Pg.32]

Sucrose+acceptor= P-D-fructofuranosyl 3-dehydro-ot-D-allopyranoside + reduced acceptor (EC 1.1.99.13)... [Pg.80]

Methyl 3-azido-4-0-benzoyl-6-bromo-2,3,6-trideoxy-2-fluoro-a-D-allopyranoside... [Pg.82]

Treatment of benzyl 2-acetamido-3,4-anhydro-2-deoxy-6-C>-trityl-a-D-allopyranoside (412) with tetrabutylammonium fluoride [BU4NF in refluxing (refl.) MeCN, 24 h] gave, under diaxial ring-opening, benzyl 2-acetamido-2,4-dideoxy-4-fluoro-6-f9-trityl-a -D-gulopyranoside (413), in... [Pg.163]

D-allopyranoside (421) was treated similarly (KHFj, ethylene glycol, 160°, 4 h), the 3-fluoro-D- /wco derivative 422 (42%) was obtained mainly, contrary to the Fiirst-Plattner rule, together with the 2-deoxy-2-fluoro-D-a/rro derivative 423 (17%). [Pg.164]

C17H23Br09 Methyl 2,3-anhydro-6-bromo-6-deoxy-4-0-(4,6-di-0-ace-tyl-2,3-dideoxy-a-D-erythro-hex-2-enopyranosyl)-a-D-allopyranoside (MBEHAP)98... [Pg.248]

C12H22Ou Ca2+ Cl2 5 H2O a-D-Allopyranosyl a-D-allopyranoside calcium chloride, pentahydrate (alio,alio-trehalose calcium chloride, pentahydrate) ALTRCA 38 451... [Pg.391]

Similarly, a series of cyclophosphamides 143-145 were synthesized in good yields (78-87%) with very high diastereoselectivity by reacting alkyl 2-amino-4,6-0-benzylidene-2-deoxy-D-allopyranosides 140-142 with /V,/V-bis-(2-chlorocthyl) amidophosphoryl dichloride 138. Subsequent hydrogenolysis of cyclophosphamides 143-145 gave excellent yields (85-90%) of cyclophosphamides 146-148 which show higher hydrophilicity than their precursors (Scheme 41) [72],... [Pg.125]

Reactivity at 0-3, in addition to that at 0-4 and 0-6, was observed with methyl )3-D-galactopyranoside, which, when treated with sulfuryl chloride, yielded methyl 3,4,6-trichloro-3,4,6-trideoxy-/J-D-allopyranoside 2-(chlorosulfate) in 56% yield.352 In contrast, under similar conditions, methyl a-D-galactopyranoside gave352 methyl 4,6-dichloro-4,6-dideoxy-a-D-glucopyranoside 2,3-di(chlorosulfate). Further examples of the dependence of the reactivity on the configuration of C-l are the conversion of methyl 4,6-0-benzylidene-/3-D-glucopyranoside into methyl 4,6-0-benzylidene-3-chloro-3-deoxy-/3-i>allopyranoside by sulfuryl chloride,352 and of methyl 4,6-0-benzylidene-a-D-glucopyranoside, under similar conditions, into the 2,3-di(chlorosulfate).355... [Pg.74]

An important step in the synthesis of paratose (3,6-dideoxy-n-rtfoo-hexose) involved the conversion of methyl 3-chloro-3-deoxy-/8-D-allopyranoside into methyl 3,6-dichloro-3,6-dideoxy-/8-D-allo-pyranoside in 33% yield.359... [Pg.75]

On treatment with 30 equivalents of methanesulfonyl chloride in N,N-dimethylformamide for 8 days at 65°, methyl /3-maltoside gave a mixture of methyl 3,6-dichloro-4-0-(6-chloro-6-deoxy-a-D-glucopyranosyl)-3,6-dideoxy-/3-D-allopyranoside, isolated in 46%... [Pg.81]

In the aldohexopyranose series, treatment of methyl 2,3-anhydro-4,6-di-O-methyl-a-D-allopyranoside (34), or of the corresponding 4,6-diacetate (39), with hydrogen tetrafluoroborate in hydrogen fluoride at 70° afforded121 the corresponding derivatives of 2-deoxy-2-fluoro-D-al-tropyranosyl fluoride (35 and 40) and 3-deoxy-3-fluoro-D-glucopyrano-syl fluoride (36 and 41). Compounds 35 and 36 were hydrolyzed, and... [Pg.215]

Y. Ali and A. C. Richardson, The reduction of azides with sodium borohydride. A convenient synthesis of methyl 2-acetamido-2-deoxy4,6-0-benzylidene-a-D-allopyranoside, Carbohydr. Res., 5 (1967) 441 448. [Pg.62]

Y. Ali, A. C. Richardson, C. F. Gibbs, and L. Hough, Some further ring-opening reactions of methyl 4,6-0-benzylidene-2,3-dideoxy-2,3-epimino-a-D-allopyranoside and its derivatives, Carbohydr. Res., 1 (1968) 255-271. [Pg.62]

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