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Interglycosidic Acetals IV. Preparation and Regioselective Cleavage of Phenyl 2,2': 4,6: 4',6'-Tri-O-benzylidene-1-thio-.BETA.-laminaribiosides.
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- Sakairi Nobuo
- Division of Bioscience, Graduate School of Environmental Earth Science, Hokkaido University
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- Okazaki Yasunori
- Division of Bioscience, Graduate School of Environmental Earth Science, Hokkaido University
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- Furukawa Jun-ichi
- Division of Bioscience, Graduate School of Environmental Earth Science, Hokkaido University
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- Kuzuhara Hiroyoshi
- Department of Engineering, Saitama University
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- Nishi Norio
- Division of Bioscience, Graduate School of Environmental Earth Science, Hokkaido University
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- Tokura Seiichi
- Division of Bioscience, Graduate School of Environmental Earth Science, Hokkaido University
Bibliographic Information
- Other Title
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- Interglycosidic Acetals IV. Preparation and Regioselective Cleavage of Phenyl 2,2′ : 4,6 : 4′,6′-Tri-<i>O</i>-benzylidene-1-thio-<i>β</i>-laminaribiosides
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Description
A (+)-10-Camphorsulfonic acid-catalysed acetal exchange reaction of phenyl 1-thio-β-laminaribioside using 3.5 molar equivalents of α,α-dimethoxytoluene gave a tris(benzylidene acetal), which was isolated and characterized as phenyl 3′-O-acetyl-2,2′ : 4,6 : 4′,6′-tri-O-benzylidene-1-thio-β-laminaribioside, and the corresponding 3′-O-benzyl derivative 6. Upon a treatment with pyridinium p-toluenesulfonate, the interglycosidic 2,2′-acetal in 6 underwent selective cleavage to give the 2,2′-diol. Additionally, a reductive ring-opening reaction of 6 with lithium aluminium hydride/anhydrous aluminium chloride, followed by O-acetylation, gave the 2,6,6′-O-acetyl-4,2′,3′,4′-tetra-O-benzyl derivative in 73% yield. A different regioselectivity was observed in the reduction of 6 with borane-trimethylamine adduct/anhydrous aluminium chloride or sodium cyanotrihydroborate/methanesulfonic acid, giving the corresponding 2,4,4′-triol as the major product.
Journal
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- Bulletin of the Chemical Society of Japan
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Bulletin of the Chemical Society of Japan 71 (3), 679-683, 1998
The Chemical Society of Japan
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Keywords
Details 詳細情報について
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- CRID
- 1390282679097030272
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- NII Article ID
- 130004150029
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- ISSN
- 13480634
- 00092673
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- Text Lang
- en
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- Data Source
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- JaLC
- Crossref
- CiNii Articles
- OpenAIRE
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- Abstract License Flag
- Disallowed