1986
DOI: 10.1016/0008-6215(86)80004-0
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The synthesis of some seven-carbon sugars via the osmylation of olefinic sugars

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Cited by 58 publications
(15 citation statements)
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“…After reduction with diisobutylaluminium hydride and catalytic bishydroxylation of 70 and 74 with osmium tetroxide, respectively, separation of the isomers is feasible via benzoylation to separate the L-glycero-L-gulo derivative 71 from the D-glycero-D-manno-heptoside 72, or via acetylation to isolate the crystalline L-glycero-D-manno-heptoside derivative 76 " Fig. (14)" [134,135]. Although the number of steps is high, the procedure is reliable to give multi-gram amounts of the 1 and 2.…”
Section: B) Synthesis Of Heptose Phosphatesmentioning
confidence: 99%
“…After reduction with diisobutylaluminium hydride and catalytic bishydroxylation of 70 and 74 with osmium tetroxide, respectively, separation of the isomers is feasible via benzoylation to separate the L-glycero-L-gulo derivative 71 from the D-glycero-D-manno-heptoside 72, or via acetylation to isolate the crystalline L-glycero-D-manno-heptoside derivative 76 " Fig. (14)" [134,135]. Although the number of steps is high, the procedure is reliable to give multi-gram amounts of the 1 and 2.…”
Section: B) Synthesis Of Heptose Phosphatesmentioning
confidence: 99%
“…As an additional example of utilization in a synthetic route, we applied our setup and methodology within the established synthetic approach towards d - glycero - d - manno heptose 9 (Scheme 4) [34, 35], which is the biological precursor of 3 . The key intermediate 5 (derived from d -mannose in multiple steps) underwent OsO 4 mediated dihydroxylation to deliver dd - manno -isomer 6 as a mixture with the minor ll - gulo isomer 7 [34, 35].…”
Section: Demonstration Of Successful Upscaling To Multigram Quantitiesmentioning
confidence: 99%
“…5) were prepared by hydrazinolysis of pure D-xylose and D-arabinose, respectively, following literature procedures. 13 Heptopyranosides were synthesized by addition of allyloxymethyl magnesium chloride to D-manno-aldehyde 6 (Scheme 1) followed by deprotection of the primary hydroxyl group by (PPh 3 ) 3 RhCl and Dabco to furnish a mixture of products.…”
Section: Synthesis Of Acyclic Diols and Triolsmentioning
confidence: 99%
“…So far structural determination studies on this class of compounds have been limited to NMR, optical rotation, and melting point measurements of derivatives requiring, in most cases, large amounts of material. 3 As part of our ongoing efforts to develop new methodologies for assigning absolute configurations of acyclic systems using the exciton chirality circular dichroic method, 4 we have undertaken studies on heptopyranosides and heptofuranosides in order to devise a microscale approach for their structural elucidation.…”
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confidence: 99%