methyl 4,6-dideoxy-4-<<<2,6-dideoxy-4-S-<4-<<3-O-methyl-α-L-rhamnopyranosyl>oxy>-5-iodo-2,3-dimethoxy-6-methylbenzoyl>-4-thio-β-D-ribo-hexopyranosyl>oxy>amino>-2-O-<2,4-dideoxy-4-(ethylamino)-3-O-methyl-α-L-threo-pentopyranosyl>-β-D-glucopyranoside | 129834-73-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4,6-dideoxy-4-<<<2,6-dideoxy-4-S-<4-<<3-O-methyl-α-L-rhamnopyranosyl>oxy>-5-iodo-2,3-dimethoxy-6-methylbenzoyl>-4-thio-β-D-ribo-hexopyranosyl>oxy>amino>-2-O-<2,4-dideoxy-4-(ethylamino)-3-O-methyl-α-L-threo-pentopyranosyl>-β-D-glucopyranoside
• 英文别名: methyl 4,6-dideoxy-4-<<<2,6-dideoxy-4-S-<4-<<6-deoxy-3-O-methyl-α-L-mannopyranosyl>oxy>-5-iodo-2,3-dimethoxy-6-methylbenzoyl>-4-thio-β-D-ribo-hexopyranosyl>pxy>amino>-2-O-<2,4-dideoxy-4-(N-ethylamino)-3-O-methyl-α-L-xylopyranosyl>-β-D-glucopyranosi；methyl 4,6-dideoxy-4-<<(2,4,6-trideoxy-4-<<4-<(6-deoxy-3-O-methyl-α-L-mannopyranosyl)oxy>-5-iodo-2,3-dimethoxy-6-methylbenzoyl>thio>-β-D-ribo-hexopyranosyl)oxy>amino>-2-O-<2,4-dideoxy-4-(ethylamino)-3-O-methyl-α-L-threo-pentopyranosyl>-β-D-glucopy..；calicheamicin γ₁^I；methyl 4,6-dideoxy-4-{[(2,6-dideoxy-4-S-{4-[(3-O-methyl-α-L-rhamnopyranosyl)oxy]-5-iodo-2,3-dimethoxy-6-methylbenzoyl}-4-thio-β-D-ribo-hexopyranosyl)oxy]amino}-2-O-[2,4-dideoxy-4-(ethylamino)-3-O-methyl-α-L-threo-pentopyranosyl]-β-D-glucopyranoside；Calicheamicin Gamma-1-Oligosaccharide；S-[(2R,3S,4S,6S)-6-[[(2R,3S,4S,5R,6R)-5-[(2S,4S,5S)-5-(ethylamino)-4-methoxyoxan-2-yl]oxy-4-hydroxy-6-methoxy-2-methyloxan-3-yl]amino]oxy-4-hydroxy-2-methyloxan-3-yl] 4-[(2S,3R,4R,5S,6S)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy-5-iodo-2,3-dimethoxy-6-methylbenzenecarbothioate
• CAS: 129834-73-7
• 化学式: C₃₈H₆₁IN₂O₁₇S
• 分子量: 976.876
• InChiKey: LLRIDSCDUGRTJE-MKLYLBDDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  59
• 可旋转键数：
  17
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  258
• 氢给体数：
  6
• 氢受体数：
  20

反应信息

• 作为反应物：
  描述：

  methyl 4,6-dideoxy-4-<<<2,6-dideoxy-4-S-<4-<<3-O-methyl-α-L-rhamnopyranosyl>oxy>-5-iodo-2,3-dimethoxy-6-methylbenzoyl>-4-thio-β-D-ribo-hexopyranosyl>oxy>amino>-2-O-<2,4-dideoxy-4-(ethylamino)-3-O-methyl-α-L-threo-pentopyranosyl>-β-D-glucopyranoside 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 methyl 4,6-dideoxy-4--5,6-dimethoxy-2-methylbenzoyl>thio>-β-D-ribohexopyranosyl)oxy>amino>-2-O-(2,4-dideoxy-4-(ethylamino)-3-O-methyl-α-L-threo-pentopyranosyl)-β-D-glucopyranoside
  参考文献：
  名称：

  Li, Tianhu; Zeng, Zijian; Estevez, Virginia A., Journal of the American Chemical Society, 1994, vol. 116, # 9, p. 3709 - 3715

  摘要：

  DOI：
• 作为产物：
  描述：

  phenyl 2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside 在 吡啶 、 4-二甲氨基吡啶 、 ruthenium trichloride 、 lithium hydroxide 、 sodium periodate 、 2,6-二叔丁基-4-甲基吡啶 、 4 A molecular sieve 、 四丁基氟化铵 、 水 、 二正丁基氧化锡 、 溶剂黄146 、 三乙胺 、 间氯过氧苯甲酸 、 三丁基氧化锡 作用下， 以 四氢呋喃 、 四氯化碳 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 111.66h， 生成 methyl 4,6-dideoxy-4-<<<2,6-dideoxy-4-S-<4-<<3-O-methyl-α-L-rhamnopyranosyl>oxy>-5-iodo-2,3-dimethoxy-6-methylbenzoyl>-4-thio-β-D-ribo-hexopyranosyl>oxy>amino>-2-O-<2,4-dideoxy-4-(ethylamino)-3-O-methyl-α-L-threo-pentopyranosyl>-β-D-glucopyranoside
  参考文献：
  名称：

  亚砜糖基化法简明合成加利车霉素低聚糖

  摘要：

  报道了加利车霉素寡糖的短合成。所有糖苷键均使用亚砜糖基化反应构建，证明了该方法的有效性。已开发出一种在寡糖中引入 NO 糖苷键的通用方法，并用于构建连接环 A 和 B 的 NO 键。在合成的最后一步，加利车霉素寡糖的两半以完全脱保护的形式偶联。这种会聚合成允许快速构建加利车霉素寡糖的衍生物，以测试特定结构特征在 DNA 结合中的重要性

  DOI：

  10.1021/ja00084a018

文献信息

• Groneberg; Miyazaki; Stylianides, Journal of the American Chemical Society, 1993, vol. 115, # 17, p. 7593 - 7611
  作者：Groneberg、Miyazaki、Stylianides、Schulze、Stahl、Schreiner、Suzuki、Iwabuchi、Smith、Nicolaou

  DOI：——

  日期：——
• Studies Related to the Carbohydrate Sectors of Esperamicin and Calicheamicin: Definition of the Stability Limits of the Esperamicin Domain and Fashioning of a Glycosyl Donor from the Calicheamicin Domain
  作者：Randall L. Halcomb、Serge H. Boyer、Mark D. Wittman、Steven H. Olson、Derek J. Denhart、Kevin K. C. Liu、Samuel J. Danishefsky

  DOI：10.1021/ja00126a013

  日期：1995.5

  The core trisaccharide regions of esperamicin and the aryltetrasaccharide region of calicheamicin have been synthesized. The minimum protection modalities necessary to stabilize structures against rearrangement to an isomeric azafuranose series were ascertained (see compounds 12 and 65). Deprotection of the 2-(trimethylsilyl)ethoxycarbonyl carbamate from 65 led to azafuranose 14 characterized as methyl glycoside 15. Using this insight, it was possible to fashion, for the first time, a pre-glycosyl donor (see compound 128) corresponding to the complete arylsaccharide sector of calicheamicin gamma(1)(I) at the oxidation level of the domain. Among the key assembly strategies were the conversion of alpha-thiophenylpseudoglycals to allal derivatives (see 44 --> 45); the interfacing of epoxide-mediated glycosylation with iodoglycosylation (see 30 --> 47 --> 48); the synthesis of hydroxylamine glycosides via triflate displacement (see 61 + 91 --> 101); and a new route to p-hydroxybenzonitriles (see formation of 86).
• Halcomb, Randall L.; Boyer, Serge H.; Danishefsky, Samuel J., Angewandte Chemie, 1992, vol. 104, # 3, p. 314 - 317
  作者：Halcomb, Randall L.、Boyer, Serge H.、Danishefsky, Samuel J.

  DOI：——

  日期：——
• Concise Synthesis of the Calicheamicin Oligosaccharide Using the Sulfoxide Glycosylation Method
  作者：Soong Hoon Kim、David Augeri、Dan Yang、Daniel Kahne

  DOI：10.1021/ja00084a018

  日期：1994.3

  A short synthesis of the calicheamicin oligosaccharide is reported. All the glycosidic linkages have been constructed using the sulfoxide glycosylation reaction, demonstrating the efficacy of the method. A general method to introduce N-O glycosidic linkages in oligosaccharides has been developed and employed to construct the N-O bond that connects rings A and B. In the final step of the synthesis,

  报道了加利车霉素寡糖的短合成。所有糖苷键均使用亚砜糖基化反应构建，证明了该方法的有效性。已开发出一种在寡糖中引入 NO 糖苷键的通用方法，并用于构建连接环 A 和 B 的 NO 键。在合成的最后一步，加利车霉素寡糖的两半以完全脱保护的形式偶联。这种会聚合成允许快速构建加利车霉素寡糖的衍生物，以测试特定结构特征在 DNA 结合中的重要性
• Li, Tianhu; Zeng, Zijian; Estevez, Virginia A., Journal of the American Chemical Society, 1994, vol. 116, # 9, p. 3709 - 3715
  作者：Li, Tianhu、Zeng, Zijian、Estevez, Virginia A.、Baldenius, Kai U.、Nicolaou、Joyce, Gerald F.

  DOI：——

  日期：——