Process for preparing isepamicin

Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives

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536 185, 536 186, C07H 100

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054420474

ABSTRACT:
An improved process for converting gentamicin B to isepamicin comprising forming 3,6'-di-N-formylgentamicin B, acylating the 1-amino group with an N-protected (S)-isoserine compound and removing all the blocking groups under conditions which result in high yields of isepamicin. A novel formylating agent, 2-formylmercaptobenzothiazole, and intermediate compounds are also disclosed.

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Tsuchiya, et al. Tetrahedron Letters No. 51, pp. 4951-4954 (1979).
Thomas, et al. Tetrahedron Letters, vol. 21, pp. 4981-4984 (1980).
Greenstein, et al. Chemistry of the Amino Acids, vol. 2, John Wiley & Sons, pp. 920-921.
Greene Protective Groups in Organic Synthesis, John Wiley & Sons (1981) p. 52.

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