Stereoselective synthesis of 1-α-cellobiosyloxy-2(R)- and -2(S)-propanol

Sugawara, Fumio; Nakayama, Haruhiko; Ogawa, Tomoya

doi:10.1016/s0008-6215(00)81808-x

Cited by 18 publications

(4 citation statements)

References 14 publications

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“…Construction of the O2- and O4-functionalized iminosugars was accomplished following a similar synthetic strategy for both, which started with p -methoxybenzylation of the free hydroxyl function of known allyl glucopyranosides 36 and 43 (Scheme ). Deallylation of the resulting products was achieved by isomerization (Wilkinson's catalyst mediated isomerization in the case of O2-PMB 37 and KO t Bu/DMSO for O4-PMB 44 ) followed by vinyl ether hydrolysis using iodine in THF/H 2 O.…”

Section: Resultsmentioning

confidence: 99%

Development of Adamantan-1-yl-methoxy-Functionalized 1-Deoxynojirimycin Derivatives as Selective Inhibitors of Glucosylceramide Metabolism in Man

et al. 2007

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In this article, we present a straightforward synthesis of adamantan-1-yl-methoxy-functionalized 1-deoxynojirimycin derivatives. The used synthetic routes are flexible and can be used to create a wide variety of lipophilic mono- and difunctionalized 1-deoxynojirimycin derivatives. The compounds reported here are lipophilic iminosugar based on lead compound 4, a potent inhibitor of the three enzymes involved in the metabolism of the glycosphingolipid glucosylceramide. Iminosugar-based inhibitors of glucosylceramide synthase, one of these three enzymes, have attracted increasing interest over the past decade due to the crucial role of this enzyme in glycosphingolipid biosynthesis. Combined with the fact that an increasing number of pathological processes are being linked to excessive glycosphingolipid levels, glucosylceramide synthase becomes a very attractive therapeutic and research target. Our results presented here demonstrate that relocating the lipophilic moiety from the nitrogen atom to other positions on the 1-deoxynojirimycin ring system does not lead to a more potent or selective inhibitor of glucosylceramide synthase. The beta-aza-C-glycoside analogue (17) retained the best inhibitory potency for glucosylceramide synthase and is a more potent inhibitor than the therapeutic agent N-butyl-1-deoxynojirimycin (3), marketed as treatment for Gaucher disease under the commercial name Zavesca.

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Section: Resultsmentioning

confidence: 99%

Development of Adamantan-1-yl-methoxy-Functionalized 1-Deoxynojirimycin Derivatives as Selective Inhibitors of Glucosylceramide Metabolism in Man

et al. 2007

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“…Glycosyl acceptor 8 was prepared from the known methyl 2-acetamido-2-deoxy-β--glucopyranoside 1 (Scheme 1). [11] Thus, deacetylation of 1 under Zemplén conditions, followed by selective protection of the 4,6-diol of the resulting 2 as a benzylidene acetal by treatment with benzaldehyde dimethyl acetal [12] in the presence of catalytic camphor-10-sulfonic acid in DMF, gave partially protected 3. N-Deacetylation of 3 with Ba(OH) 2 ·8H 2 O [13] afforded the free amine 4 in 87% overall yield, and this compound was treated with the diazo transfer reagent triflic azide (TfN 3 ) in the presence of 4-(dimethylamino)pyridine (DMAP) in methanol [14] to give the corresponding 2-azido-2-deoxyglucopyranoside 5 in 73% yield.…”

Section: Resultsmentioning

confidence: 99%

Selectively Protected Disaccharide Building Blocks for Modular Synthesis of Heparin Fragments

Haller

Boons

2002

Eur. J. Org. Chem.

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“…The ring opening reaction with nucleophiles (Nu -) should lead to the formation of rhynchosporoside and related substances. To obtain glucopyranosides (4,5), methyl 2,3,4,6-tetra-0-benzyl-l-deoxy-l-thio-{3-D-glucopyranoside (12) was prepared from pentaacetyl glucose in a 81.2% overall yield. The methylthio group was easily converted into chloride via a hydroxyl group (13) with thionyl chloride and dimethylformamide 8 ) in a quantitive yield.…”

Section: And Discussionmentioning

confidence: 99%