methyl 3,4-di-O-acetyl-2,6-dideoxy-α-D-ribo-hexopyranoside | 33650-60-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3,4-di-O-acetyl-2,6-dideoxy-α-D-ribo-hexopyranoside
• 英文别名: methyl-(di-O-acetyl-α-D-ribo-2,6-dideoxy-hexopyranoside)；Methyl-(di-O-acetyl-α-D-ribo-2,6-didesoxy-hexopyranosid)；α-Methyl-3,4-di-O-acetyl-D-digitoxosid；[(2R,3R,4S,6S)-3-acetyloxy-6-methoxy-2-methyloxan-4-yl] acetate
• CAS: 33650-60-1
• 化学式: C₁₁H₁₈O₆
• 分子量: 246.26
• InChiKey: YYOUDJJKCIBTNG-LUGRLLCRSA-N

物化性质

• 熔点：
  82-83 °C(Solv: ethyl ether (60-29-7); pentane (109-66-0))
• 沸点：
  300.5±42.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.63
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  71.06
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl 3,4-di-O-acetyl-2,6-dideoxy-α-D-ribo-hexopyranoside 在 三氟甲磺酸三甲基硅酯 、 三氟化硼乙醚 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 6.17h， 生成 (3aR,4R,7aS)-2,2,4-trimethyl-6-phenylsulfanyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran
  参考文献：
  名称：

  通过糖基供体的构象辅助实现高度立体选择性的糖基化

  摘要：

  通过使用刚性糖基供体2的构象辅助，实现了2-脱氧-D-岩藻糖的高度α-立体选择性糖基化。2的糖基化的选择性比具有正常椅子构象的3的糖基化的选择性高得多。

  DOI：

  10.1016/0040-4039(91)80435-9
• 作为产物：
  描述：

  methyl 2-deoxy-4,6-O-benzylidene-α-D-ribo-hexopyranoside 在 4-二甲氨基吡啶 吡啶 、 N-溴代丁二酰亚胺(NBS) 、 lithium aluminium tetrahydride 、 barium carbonate 作用下， 以 四氢呋喃 、 四氯化碳 为溶剂， 反应 26.7h， 生成 methyl 3,4-di-O-acetyl-2,6-dideoxy-α-D-ribo-hexopyranoside
  参考文献：
  名称：

  Substrate Flexibility of Vicenisaminyltransferase VinC Involved in the Biosynthesis of Vicenistatin

  摘要：

  A glycosyltransferase VinC is involved in the biosynthesis of antitumor beta-glycoside antibiotic vicenistatin. It catalyzes a glycosyl transfer reaction between dTDP-alpha-D-vicenisamine and vicenilactam. Previous identification of its broad substrate specificity toward various glycosyl acceptors enabled us to explore the potential of VinC for glycodiversification. In vitro study of the substrate specificity toward several dTDP-sugars with vicenilactam established that VinC displayed activities with alpha-anomers of several dTDP-2-deoxy-D-sugars such as mycarose, digitoxose, olivose, and 2-deoxyglucose to afford respective beta-glycosides. Notably, beta-anomers of dTDP-2-deoxy-D-sugars also appeared to be accepted by VinC to form alpha-glycosides. Furthermore, VinC is capable of catalyzing glycosyl transfer reactions from both the alpha-anomer and beta-anomer of dTDP-L-mycarose, respectively, into beta-glycoside and alpha-glycoside. These results indicate that VinC is a unique glycosyltransferase possessing broad substrate specificity. The mechanism of this axially oriented glycosidic bond formation from the equatorially oriented dTDP-sugar might be explained by conformational change of dTDP-sugar to a boat conformation during the glycosyl transfer reaction. To apply these features of VinC for glycodiversification, 22 sets of structurally diverse glycosides were constructed using unnatural glycosyl donors and acceptors.

  DOI：

  10.1021/ja0685250

文献信息

• Die Konstitution der isomeren Acetyldigitoxine. 48. Mitteilung über Herzglykoside
  作者：Max Kuhn、Heinz Lichti、Albert von Wartburg

  DOI：10.1002/hlca.19620450318

  日期：——

  The reaction with phenylisocyanate transformed both acetyldigitoxin-α and acetyldigitoxin-β into their tris-phenylurethanes (I and IX, respectively). By degradation of these derivatives, the constitutions of the degluco-lanatosides could be elucidated. In acetyldigitoxin-α, the characteristic acetyl group is attached to C-3 of the terminal digitoxose unit, while the acetyl group of acetyldigitoxin-β

  与苯基异氰酸酯的反应将乙酰基数字毒菌素-α和乙酰基数字毒菌素-β都转化为它们的三苯基氨基甲酸酯（分别为I和IX）。通过降解这些衍生物，可以阐明去葡萄糖-羊毛脂苷的组成。在乙酰二氧肟酸-α中，特征性的乙酰基连接至末端三氧嘧啶糖单元的C-3，而乙酰基氧还蛋白-β的乙酰基位于末端糖的C-4。异构体乙酰可可恶素的可逆重排代表酰基迁移。
• Krystallisierte 2-Desoxy-d-allose und eine neue Synthese derd-Digitoxose Desoxyzucker 16. Mitteilung
  作者：M. Gut、D. A. Prins

  DOI：10.1002/hlca.19470300517

  日期：1947.8.1