Synthesis of 5-O- and 6-O-methyldihydrostreptomycin.

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概要

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• 5-<I>O</I>- and 6-<I>O</I>-Methyldihydrostreptomycin have been prepared from dihydrostreptomycin by a sequence of reactions involving methylation of a selectively protected derivative (<B>4</B>) with diazomethane in the presence of tin(II) chloride. The structures of the final products were confirmed by their <SUP>13</SUP>C-NMR spectra and the TACu method.

• 公益社団法人 日本化学会の論文

著者

• Kobayashi Yoshihiko

  Institute For Solid State Physics University Of Tokyo

• Tsuchiya Tsutomu

  Institute of Bioorganic Chemistry

• Umezawa Sumio

  Institute of Bioorganic Chemistry

• Kobayashi Yoshihiko

  Institute of Bioorganic Chemistry

• Kishi Teruo

  Institute of Bioorganic Chemistry

• Koga Naokazu

  Institute of Bioorganic Chemistry

関連論文

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• Reactions of benzyl 2-benzyloxycarbonylamino-2-deoxy-3-O-mesyl-.ALPHA.-D-gluco- and -.ALPHA.-D-allopyranoside derivative with iodide.
• Syntheses of 23-C-substituted derivatives of mycaminosyl tylonolide and 4'-deoxymycaminosyl tylonolide.
• Transformation of dihydrostreptomycin into 3"-deoxydihydrostreptomycin.
• A synthesis of 3'-deoxybutirosin B.
• Structural studies on the cyclic carbamate derivatives of kanamycin A.
• Synthesis of 5-O- and 6-O-methyldihydrostreptomycin.
• Studies on O.RAR.N acyl migration in O-acyl-2-deoxystreptamines.
• Syntheses of 1-epikanamycin A and its 1-N-((S)-4-amino-2-hydroxybutyryl) derivative.
• Syntheses of lividomycin B analogues, 5-O-(3-O-(6-amino-6-deoxy-.BETA.-L-idopyranosyl)-.BETA.-D-ribofuranosyl)-3'-deoxyparomamine and 5-O-(2-O-(6-amino-6-deoxy-.BETA.-L-idopyranosyl)-.BETA.-D-ribofuranosyl)-3'-deoxyparomamine.
• Syntheses of 2',3'-dideoxykanamycin A, 2',3'-dideoxyamikacin and related substances.
• The total synthesis of neomycin C.
• Syntheses of recyclized macrolide antibiotics and related derivatives from mycaminosyltylonolide.
• Reactions of 2-guanidino-1-cyclohexanol with ketals and acetals.
• Synthesis of 5"-deoxy-5"-fluorolividomycin B.
• Synthesis of 2-amino-2,3-dideoxy-L-ribohexose.
• Synthesis of a masked derivative of 3'-deoxydihydrostreptobiosamine, a precursor for the synthesis of 3"-deoxydihydrostreptomycin.
• A synthesis of neamine.
• Synthesis of a lividomycin B analogue, 5-O-[3-O-(2-amino-2-deoxy-.ALPHA.-D-glucopyranosyl)-.BETA.-D-ribofuranosyl]-3'-deoxyparomamine.

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