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Tetrahedron

Volumn 41, Issue 17, 1985, Pages 3455-3462

Total synthesis of acosamine and daunosamine utilizing a diastereoselective intramolecular [3+2] cycloaddition

(2) Wovkulich, P M a Uskokovic M R a

a HOFFMANN LA ROCHE INC (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DAUNOSAMINE;

ACOSAMINE; DRUG ANALYSIS; DRUG IDENTIFICATION; DRUG SYNTHESIS; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; THEORETICAL STUDY;

EID: 0022403658 PISSN: 00404020 EISSN: None Source Type: Journal
DOI: 10.1016/S0040-4020(01)96700-6 Document Type: Article

Times cited : (96)

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- For a listing of previous synthetic routes to d, l or dl-acosamine (3-amino-2,3,6-trideoxyl-L-arabino-hexose), daunosamine (3-amino-2,3,6-trideoxy-L-lyxo-hexose) and derivatives see footnote 2, in Ref. 3. See also
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26
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49
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51
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- The unwanted reaction of 9d → 15 is apparently an acid catalyzed reaction which is further aggravated by the use of more polar solvents Omission of an acid catalyst slows down the exchange reaction considerably and the lifetime of 9b is consequently extended Alternate routes to the nitrone 12d are being evaluated.

52
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- Karabatsos¹ Fenoglio²

53
- 84918055465
- 3—C—N—C angle is 60° (cf. ii).

54
- 84918055464
- 11 has suggested that favorable orbital interactions would arise when the carbon-oxygen bond is orthogonal to the nitrone in the transition state. The importance of such a rotamer in the present system is uncertain.

55
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56
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- 6i,j

57
- 84918055462
- We thank F. Arcamone for providing an authentic sample of methyl - 2,3,6 - trideoxy - 3 - trifluoroacetamido - α - L - arabinohexopyranoside (21e).

58
- 84918055461
- The structure was confirmed by an X-ray crystallographic analysis. We thank Dr J. Blount and his staff for making this determination.

59
- 84918055460
- These conditions were not optimized.

60
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