Aminocyclitols. XVII. A Facile Synthesis of 2-Deoxystreptamine

Suami, Tetsuo; Lichtenthaler, Frieder W.; Ogawa, Seiichiro; Nakashima, Yasuo; Sano, Hiroshi

doi:10.1246/bcsj.41.1014

Cited by 17 publications

(8 citation statements)

References 17 publications

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“…Early syntheses in the laboratories of Nakajima et al (2) and Suami et al (3) embodied elegant concepts in certain stages but, being predicated on the use of achiral starting materials such as "benzeneglycols" (cyclohexadienediols) and myo-inositol, they did not lend themselves to, nor were they intended for, the synthesis of stereospecifically substituted, chiral derivatives of 21. The same was true for an approach departing from 4,6-dinitropyrogallol (4) and for the more recent and convenient, high-yielding synthesis from 4,5-epoxycyclohexene reported by Prinzbach et al (5).…”

Section: -Deoxystreptaminementioning

confidence: 99%

A chiral approach to 2-deoxystreptamine

Baer¹,

Arai²,

Radatus³

et al. 1987

Can. J. Chem.

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A new synthesis of 2-deoxystreptamine (21), a component of numerous antibiotics, was developed. Starting from D-mannose, it proceeds through chiral intermediates and is designed to furnish starting points for the preparation of stereospecifically modified derivatives of the meso compound 21. 1 ,2-Dideoxy-I-nitro-D-manno-heptitol (2), obtainable from mannose by the nitromethane method, was protected as the 4,5:6,7-di-0-isopropylidene derivative 4, which was mesylated or triflated in position 3. From the sulfonic esters (5 and 6) two different routes involving displacement by azide, partial deacetonation at 0-6,7, periodate oxidation, and cyclization of the resulting nitroaldohexose derivatives converged to give 1~-(1,3/2,4,6)- On a mis au point une nouvelle synthbse de la dCsoxy-2 streptamine (21), un composant de plusieurs antibiotiques. Utilisant le D-mannose comme produit de dCpart, cette synthbse procbde par le biais d'intermkdiaires chiraux et il est prCvu qu'elle pourra fournir des points de dCpart pour la prkparation de dCrivCs modifiCs d'une f a~o n stCrCospCcifique du composC me's0 21. Le didCsoxy-1,2 nitro-1 D-manno-heptitol (2), que l'on peut obtenir a partir du mannose en faisant appel a la mCthode au nitromethane, a Ct C protegC sous la forme du dCrivC di-0-isopropylidbne-4,5:6,7 (4) et l'on aensuite transforme en dCrivC mCsylC ou triflC en position 3. A partir des esters sulfoniques (5 et 6), deux voies differentes impliquant une substitution par un ion azoture, une dtacCtonation partielle en 0-6,7, une oxydation periodique et une cyclisation des dCriv6s nitroaldohexoses qui en rCsultent convergent pour donner l'azido-6 0-isopropylidbne-l,2 nitro-4 cyclohexanetriol-l,2,3 1~(1,3/2,4,6) (19), un intermidiaire clC. L'hydrogCnation catalytique fournit ensuite la 0-isopropylidkne-4,5 dCsoxy-2 streptamine optiquement active (23) qui a Ct C isolCe sous la forme de son dCrivC N,N1-diacCtylC (24). La dtacCtonation du composC 19 fournit l'azidonitrotriol 15 qui est rCduit en 21. On discute de I'utilitC potentielle d'intermediaires chiraux dans les synthbses stCrCospCcifiques d'aminoglycosides contenant la dCsoxystreptamine.[Traduit par la revue]

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Section: -Deoxystreptaminementioning

confidence: 99%

A chiral approach to 2-deoxystreptamine

Baer¹,

Arai²,

Radatus³

et al. 1987

Can. J. Chem.

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“…The ir spectra of the three crops of crystals were all superimposable on that of an authentic sample. 27 Pentaacetyl-2-bromo-2-deoxystreptamine-2-14C (26). Anhydrous m>'o-inosadiamine-l,3-i-14C dihydrochloride (25-14C, 290 mg, obtained by hydrolysis of labeled 12) was heated in a sealed tube with acetyl bromide (0.41 ml) and acetic anhydride (0.88 ml) and worked up as described in the preceding section for the unlabeled compound.…”

Section: Experimental Section28mentioning

confidence: 99%

“…Pentaacetyl-2-deoxystreptamine (27). A slurry of pentaacetyl-2-bromo-2-deoxystreptamine (26, 440 mg) and acetic anhydride (15.4 ml) was stirred vigorously with pulverized zinc metal (7.8 g).…”

Section: Experimental Section28mentioning

confidence: 99%

“…The infrared spectrum was superimposable on that of an authentic sample. 27 Pentaacetyl-2-deoxystreptamine-l-14C (27). A slurry of labeled 26 (220 mg), acetic anhydride (7.7 ml), and pulverized zinc (3.9 g) was treated as for the unlabeled material in the preceding section.…”

Section: Experimental Section28mentioning

confidence: 99%

“…Under conditions slightly modified from OR 25, R = R' = H; R" = OH 26, R = Ac: R' = Br; R" = H 27, R = Ac; R' = R" = H 28, R = R' = R" = H those earlier reported,26•27 we obtained a somewhat better yield (81%) in the introduction of bromine into 25. Debromination was effected by treating pentaacetyl-2bromo-2-deoxystreptamine (26) with zinc, acetic anhydride, and water at room temperature to give pentaacetyl-2-deoxystreptamine (27) in 82% yield. Compound 27 was hydrolyzed with boiling 6 N hydrochloric acid to give deoxystreptamine dihydrochloride (28) in 96% yield.…”

mentioning

confidence: 99%

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Chemistry of the neomycins. XIII. Synthesis of aminocyclitols and aminosugars via nitromethane condensations

Ogawa¹,

Rinehart²,

Kimura³

et al. 1974

J. Org. Chem.

Self Cite

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Base-catalyzed cylizations of 2-acetamido-2,6-dideoxy-6-nitro-a-D-gluco-(and -L-ido-) thiofuranosides with subsequent hydrogenations have given two known inosadiamines-streptamine and myo-inosadiamine-1,3-and two previously unknown optically active inosdiamines-lL-myo-inosadiamine-1,5 and lL-epi-inosadiamine-1,3. Starting from myo-inosadiamine-1,3, 2-deoxystreptamine was synthesized in three steps. Neosamines B and C have also been prepared. The structures of all new compounds were determined by their nmr spectra and the reaction sequences.

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