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Volumn 121, Issue 26, 1999, Pages 6176-6182

Scavenging byproducts in the sulfoxide glycosylation reaction: Application to the synthesis of ciclamycin 0

Author keywords

[No Author keywords available]

Indexed keywords

ACID ANHYDRIDE; ANTHRACYCLINE ANTIBIOTIC AGENT; CICLAMYCIN 0; SULFOXIDE; UNCLASSIFIED DRUG;

EID: 0033532859     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja990690a     Document Type: Article
Times cited : (87)

References (49)
  • 9
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    • (1990) Top. Curr. Chem. , vol.154 , pp. 285
    • Thiem, J.1    Klaffke, W.2
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    • Horton, D., Hawkins, L. D., McGarvey, G. J., Eds.; American Chemical Society: Washington, DC, Chapter 8
    • (b) Thiem, J. In Trends in Synthetic Carbohydrate Chemistry; Horton, D., Hawkins, L. D., McGarvey, G. J., Eds.; American Chemical Society: Washington, DC, 1989; Chapter 8.
    • (1989) Trends in Synthetic Carbohydrate Chemistry
    • Thiem, J.1
  • 14
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    • (d) Kolar, C.; Bosslet, K.; Czech, J.; Gerken, M.; Hermentin, P.; Hoffmann, D.; Sedlacek, H. Chapter 4 in ref 2
    • (d) Kolar, C.; Bosslet, K.; Czech, J.; Gerken, M.; Hermentin, P.; Hoffmann, D.; Sedlacek, H. Chapter 4 in ref 2.
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    • and references therein
    • For other one-pot syntheses of oligosaccharides, see: (a) Yamada, H.; Harada, T.; Takahashi, T. J. Am. Chem. Soc. 1994, 116, 7919 and references therein.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 7919
    • Yamada, H.1    Harada, T.2    Takahashi, T.3
  • 20
    • 33845470339 scopus 로고
    • Pyrromycinone, 9, was obtained by acidic hydrolysis of marcellomycin, a generous gift from Bristol-Myers Squibb. Pyrromycinone can also be obtained through known synthetic routes or through degradation of other readily available anthracyclines; see: (a) Hauser, F. M.; Mal, D. J. Am. Chem. Soc. 1984, 706, 1098.
    • (1984) J. Am. Chem. Soc. , vol.706 , pp. 1098
    • Hauser, F.M.1    Mal, D.2
  • 23
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    • Ph.D. Thesis, Princeton University
    • Raghavan, S. Ph.D. Thesis, Princeton University, 1994.
    • (1994)
    • Raghavan, S.1
  • 27
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    • There may be more than one highly reactive sulfenylating agent produced in the reaction
    • There may be more than one highly reactive sulfenylating agent produced in the reaction.
  • 35
    • 33646955207 scopus 로고    scopus 로고
    • note
    • This specific alkene was chosen for a number of reasons: it is commercially available and inexpensive, and has a sufficiently high boiling point to permit azeotroping with toluene along with the other starting materials prior to reaction.
  • 36
    • 33646958906 scopus 로고    scopus 로고
    • note
    • Norbornylene was slightly less effective than 4-allyl-1,2-dimethoxybenzene, while vinylnorbornene, vinylnaphthalene, cyclopentene, and vinyltrimethylsilane were significantly less effective. No product was formed in the presence of triphenylphosphine or thioanisole.
  • 37
    • 33646952515 scopus 로고    scopus 로고
    • note
    • For comparison, glycosylation of 15 with sulfoxide 11 in the absence of a scavenger produced 16 in 45% yield along with 18% of the corresponding trisaccharide, showing that most of the improvement in yield is a result of the scavenger. However, similar improvements in yield (ID-15%) are observed when the C ring sulfoxide is coupled. These modest improvements in yield achieved by incorporating the 2,6-dichlorophenyl sulfide become important when multiple glycosylations are conducted.
  • 39
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    • For example, sulfenylating agents are known to react with alcohols, amines, and electron-rich aromatic rings. See ref 22
    • For example, sulfenylating agents are known to react with alcohols, amines, and electron-rich aromatic rings. See ref 22.
  • 40
    • 44949268152 scopus 로고
    • In addition to activating glycosyl sulfides, sulfenylating agents have been used to activate glycosyl xanthates and glycals. For activation of xanthates, see: (a) Marra, A.; Sinay, P. Carbohydr. Res. 1990, 195, 303.
    • (1990) Carbohydr. Res. , vol.195 , pp. 303
    • Marra, A.1    Sinay, P.2
  • 47
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    • The known C ring sulfoxide 6 can be synthesized from rhamnose in seven steps (58% overall yield); see ref 7
    • The known C ring sulfoxide 6 can be synthesized from rhamnose in seven steps (58% overall yield); see ref 7.
  • 49
    • 33646957416 scopus 로고    scopus 로고
    • 13C, and mass spectra for synthetic ciclamycin 0 were identical with the spectra reported in the literature (see refs 6 and 8)
    • 13C, and mass spectra for synthetic ciclamycin 0 were identical with the spectra reported in the literature (see refs 6 and 8).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.