7-O-<2,3,6-Trideoxy-3-<6(S)-hydroxymethyl-2(R)-methoxymorpholin-4-yl>-α-L-lyxo-hexopyranosyl>-ε-isorhodomycinone | 127903-57-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 四环素类
• 英文名称: 7-O-<2,3,6-Trideoxy-3-<6(S)-hydroxymethyl-2(R)-methoxymorpholin-4-yl>-α-L-lyxo-hexopyranosyl>-ε-isorhodomycinone
• 英文别名: 7-O-[2,3,6-Trideoxy-3-(6(S)-hydroxymethyl-2(R)-methoxymorpholin-4-yl)-α-L-lyxo-hexopyranosyl]-ε-isorhodomycinone；methyl (1R,2R,4S)-2-ethyl-2,5,7,10,12-pentahydroxy-4-[(2R,4S,5S,6S)-5-hydroxy-4-[(2S,6R)-2-(hydroxymethyl)-6-methoxymorpholin-4-yl]-6-methyloxan-2-yl]oxy-6,11-dioxo-3,4-dihydro-1H-tetracene-1-carboxylate
• CAS: 127903-57-5；127995-98-6；128049-36-5
• 化学式: C₃₄H₄₁NO₁₅
• 分子量: 703.697
• InChiKey: OIJZADXXSIDXEQ-OWNBXVAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.67
• 重原子数：
  50.0
• 可旋转键数：
  7.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  242.21
• 氢给体数：
  7.0
• 氢受体数：
  16.0

反应信息

• 作为产物：
  描述：

  甲基-Β-D-吡喃半乳糖苷 在 sodium periodate 、 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 27.0h， 生成 7-O-<2,3,6-Trideoxy-3-<6(S)-hydroxymethyl-2(R)-methoxymorpholin-4-yl>-α-L-lyxo-hexopyranosyl>-ε-isorhodomycinone
  参考文献：
  名称：

  Semisynthetic ε-(iso)rhodomycins: a new glycosylation variant and modification reactions

  摘要：

  Synthesis of 7-O-(3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosyl)-e-(iso)rhodomycinones 16 and 17, and their 3'-morpholino derivatives are described. Glycosylation (trimethylsilyl triflate, 10:1 dichloro-methane-acetone, -35-degrees-) of 1-O-tert-butyldimethylsilyl-2,3,6-trideoxy-4-O-p-nitrobenzoyl-?? 3-trifluorace-tamido-beta-L-lyxo-hexopyranose (4) with e-rhodomycinone (e-RMN, 5) or e-isorhodomycinone (e-isoRMN, 6) afforded 7-O-alpha-glycosyl-e-RMN (9) and -e-isoRMN (12) in high yield. The glycosyl donors 2,3,6-trideoxy-4-O-p-nitrobenzoly-3-trifluoroacetamido-L-lyxo-hexopyranose (2) or its 1-O-trimethylsilylated alpha-anomer 3 were less suitable for the glycosylation of these aglycons. Saponification of 9 and 12 provided 16 and 17, respectively, which reacted with various 2,2'-oxydiacetaldehydes under conditions of reductive alkylation to give 3'-morpholinyl-e-(iso)rhodomycins.

  DOI：

  10.1016/0008-6215(91)80147-f

文献信息

• KOLAR, CENEK;KNEISSL, GUNTHER;KNODLER, URSULA;DEHMEL, KONRAD, CARBOHYDR. RES., 209,(1991) C. 89-100
  作者：KOLAR, CENEK、KNEISSL, GUNTHER、KNODLER, URSULA、DEHMEL, KONRAD

  DOI：——

  日期：——