The use of Grignard reagents in the synthesis of carbohydrates. III. The one-way anomerization of methyl glycofuranosides and the opening of their furanose rings.
スポンサーリンク
概要
- 論文の詳細を見る
The anomerization of methyl glycofuranoside derivatives with methylmagnesium iodide or <I>t</I>-butylmagnesium bromide occurred in a one-way manner. For example, methyl 5-<I>O</I>-benzyl-β-D-ribofuranoside (<B>3β</B>) was converted into the corresponding α-anomer (<B>3α</B>) in a 95% yield when a mixture of <B>3β</B> and <I>t</I>-butylmagnesium bromide in benzene–ether was heated at about 75 °C to remove the ether; the reverse reaction (from <B>3α</B> to (<B>3β</B>) did not proceed. The reaction of <B>3β</B> with methylmagnesium iodide gave open-chain products (33%), besides <B>3α</B> (30%). Twenty kinds of anomers were tested, and the mechanisms of the reactions were discussed. The cleavage of a benzyl- or trityl-protecting group with the Grignard reagent was also observed during the reaction.
- 公益社団法人 日本化学会の論文
著者
-
KUZUHARA Hiroyoshi
The Institute of Physical and Chemical Research (RIKEN)
-
Emoto Sakae
The Institute of Physical and Chemical Research
-
Kawana Masajiro
The Institute of Physical and Chemical Research
-
Kuzuhara Hiroyoshi
The Institute of Physical and Chemical Research
関連論文
- Regioselective Mono-2-C-iodination of Fully Methylated Cyclodextrins through Interconversions between Cyclic and Acyclic Structures
- Facile Synthesis of 6^1-O-(α-D-Galactopyranosyl)cyclomaltoheptaose from Commercially Available Branched Cyclodextrin
- Efficient and Regioselective Preparation of an Eight-membered Interglycosidic Benzylidene Derivative of β-Cyclodextrin
- Synthesis of a New Allosamidin Analog, N,N'-Diacetyl-β-Chitobiosyl Allosamizoline, and Its Inhibitory Activity against Some Chitinases
- Catalytic activities of salicylaldehyde derivatives. V. Syntheses and catalytic activities of some trimethylammonio derivatives of salicylaldehyde in the racemization of L-glutamic acid.
- The use of Grignard reagents in the synthesis of carbohydrates. I. The synthesis of deoxy and branched-chain deoxy sugars.
- The use of Grignard reagents in the synthesis of carbohydrates. III. The one-way anomerization of methyl glycofuranosides and the opening of their furanose rings.
- Preferential introduction of a pyridylmethyl group into sulfonamides as an approach to an intramolular transimination.
- Asymmetric synthesis of .ALPHA.-deuterated .ALPHA.-amino acids through nonenzymatic transamination reaction and the determination of their enantiomeric excesses.
- Optical resolution of pyridoxal-like pyridinophanes.
- A kinetic study of a Zn2+-catalyzed transamination reaction between pyridoxamine analogs with a pyridinophane structure and .ALPHA.-keto acids.
- Catalytic Activities of Salicylaldehyde Derivatives. III. An Improved Synthesis of 6-Nitrosalicylaldehyde
- Pyridoxal model compounds. II. The Diels-Alder reaction of 9-substituted 2-methoxyanthracenes.
- Formation and Reduction of 2-Acyl-1-tetralones
- The Reaction of Several o-Methoxy Aromatic Aldehydes with Ethylthioxide. Novel Substitution and Condensation
- Catalytic activities of salicylaldehyde derivatives. VII. Synthesis and catalytic activity of (2-formyl-3-hydroxyphenyl)dimethylsulfonium salt in the racemization of L-glutamic acid.
- Aldol condensation of aldehydes with ketones promoted by the copper(II) ion. Orientation to the chemical model for metalloaldolases.
- Pyridoxal Model Compounds. I. The Regioselective Formylation of Methoxy-substituted Aromatic Compounds
- Asymmetric Synthesis with Sugar Derivatives. V. The Synthesis of α-Hydroxy Acids on Insoluble Polymer Supports