Synthesis of daunosamine hydrochloride from a D-mannose starting

Details Synthesis of daunosamine hydrochloride from a D-mannose starting Synthesis of daunosamine hydrochloride from a D-mannose starting

1976-06-22

1977-05-17

Gotts, Lewis

Organic compounds -- part of the class 532-570 series

Organic compounds

Carbohydrates or derivatives

536 4, 536 18, 424180, C07G 1100

Patent

active

040243338

ABSTRACT:
A method for synthesizing daunosamine hydrochloride from methyl .alpha.-D-mannopyranoside. The major features of the preparative route involve the formation of a 2-deoxy-3-keto intermediate, whose oxime is reduced with high stereoselectivity to the D-ribo-3-amino compound, followed by a stereospecific step late in the sequence to introduce the terminal C-methyl group with inversion at C-5, to generate the required L-lyxo stereochemistry. The synthesis procedure affords daunosamine hydrochloride in 40% overall yield, with no chromatographic procedures for isolation being required in any of the steps.

REFERENCES:
evans, Carbohydrate Research, vol. 21, (1972) pp. 473-475.
Beynon et al., J. Chem. Soc. (c), 1969, pp. 272-281.
Acton et al., "Commun. to the Editor," J. of Med. Chem., 1974, vol. 17, No. 6, pp. 659-660.
Gaylord, "OXIMES," Red. w/Complex Metal Hydrides, p. 751, Intersci. Publ. NY 1956.

Affiliated with

Also associated with

Rating

Synthesis of daunosamine hydrochloride from a D-mannose starting does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Synthesis of daunosamine hydrochloride from a D-mannose starting, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Synthesis of daunosamine hydrochloride from a D-mannose starting will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-1835852