methyl 2,4-dideoxy-3-O-methyl-4-(N-acetylamino)-β-L-xylopyranoside | 128072-24-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: methyl 2,4-dideoxy-3-O-methyl-4-(N-acetylamino)-β-L-xylopyranoside
• 英文别名: N-[(3S,4S,6S)-4,6-dimethoxyoxan-3-yl]acetamide
• CAS: 128072-24-2
• 化学式: C₉H₁₇NO₄
• 分子量: 203.238
• InChiKey: DYWSYMTWKQOMOO-CIUDSAMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2,4-dideoxy-3-O-methyl-4-(N-acetylamino)-β-L-xylopyranoside 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以80%的产率得到methyl 2,4-dideoxy-4-(ethylamino)-3-O-methyl-β-L-threo-pentopyranoside
  参考文献：
  名称：

  的改进的立体选择性合成都是甲基α-和对应于E环的氨基糖成分β糖苷的加利车霉素γ 1我和埃斯波霉素阿1

  摘要：

  的E环的单糖组分（α和β端基异构体）刺孢霉素γ 1我和埃斯波霉素阿1已经通过从甲基2-脱氧- α-和β-d-ribopyranoside开始的有效和改进的立体选择性方法合成。在每种情况下，合成方法都使用环状硫酸盐和中间体活化的氮丙啶的区域选择性开环。

  DOI：

  10.1016/s0040-4020(97)00921-6
• 作为产物：
  描述：

  4-(S)-(2-formyl-1(S)-methoxyethyl)-2,2-dimethyl-3-(tert-butoxycarbonyl)oxazolidine 在 吡啶 、 对甲苯磺酸 、 zinc(II) chloride 作用下， 以 甲醇 为溶剂， 反应 36.0h， 生成 methyl 2,4-dideoxy-3-O-methyl-4-(N-acetylamino)-β-L-xylopyranoside
  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

• Preparation of the 4-ethylamino sugar of calicheamicin: Assignment of absolute configuration.
  作者：Daniel Kahne、Dan Yang、May D Lee

  DOI：10.1016/s0040-4039(00)94323-5

  日期：1990.1

  The absolute configuration of the 4-ethylamino sugar of calicheamicin is established to be 3S,4S by comparison with material obtained from asymmetric synthesis from L-serine.

  与从L-丝氨酸的不对称合成获得的材料相比，加利车霉素的4-乙基氨基糖的绝对构型被确定为3S，4S。
• Asymmetric Allylboration of 2-N,3-O-Isopropylidene-N-Boc-L-serinal: Diastereoselective Synthesis of the Calicheamicin .gamma.1I Amino Sugar
  作者：William R. Roush、J. A. Hunt

  DOI：10.1021/jo00109a008

  日期：1995.2

  Syntheses of the calicheamicin amino sugar 6 and its erythro diastereomer 7 have been completed by a sequence involving the asymmetric allylboration of N-Boc-serinal acetonide L-8 with the tartrate ester modified allylboronates (R,R)-9 and (S,S)-9, respectively. The reaction of(R,R)-9 and L-8 in toluene provides 14 with 89:11 selectivity, whereas the reaction of(S,S)-9 with L-8 in Et(2)O provides the diastereomer 15 with 90:10 selectivity. It is shown that the relatively modest diastereoselectivity of these double asymmetric reactions is compromised by the low enantiomeric purity of 8 (86-87% ee), and data are provided indicating that these reactions should be highly diastereoselective (greater than or equal to 95:5 in each case) if performed with enantiomerically pure aldehyde. The two diastereomeric homoallylic alcohols, 14 and 15, are easily elaborated into the targeted amino sugars 6 and 7 via the acetamide-substituted pyranosides 22 and 26. Methyl pyranosides 22a and 22e were shown to adopt preferentially the unexpected conformations B and D, with axial acetamide substituents, in nonpolar solvents, while the expected conformations A and C were strongly favored in d(6)-DMSO because of hydrogen bonding interactions with the solvent. The syntheses of 6 and 7 reported herein are expected to facilitate the design and synthesis of analogs of the calicheamicin aryl tetrasaccharide 3, which should prove useful in further analysis and applications of oligosaccharides as DNA binders.
• KAHNE, DANIEL;YANG, DAN;LEE, MAY D., TETRAHEDRON LETT., 31,(1990) N, C. 21-22
  作者：KAHNE, DANIEL、YANG, DAN、LEE, MAY D.

  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
• Improved stereoselective synthesis of both methyl α- and β-glycosides corresponding to the amino sugar component of the E Ring of calicheamicin γ1I and esperamicin A1
  作者：Fabrizio Badalassi、Paolo Crotti、Lucilla Favero、Franco Macchia、Mauro Pineschi

  DOI：10.1016/s0040-4020(97)00921-6

  日期：1997.10

  monosaccharide component (α and β-anomer) of the E Ring of calicheamicin γ1I and esperamicin A1 has been synthetized by an efficient and improved stereoselective procedure starting from methyl 2-deoxy-α- and β-D-ribopyranoside. The synthetic procedure makes use, in each case, of a cyclic sulphate and of the regioselective ring opening of an intermediate activated aziridine.

  的E环的单糖组分（α和β端基异构体）刺孢霉素γ 1我和埃斯波霉素阿1已经通过从甲基2-脱氧- α-和β-d-ribopyranoside开始的有效和改进的立体选择性方法合成。在每种情况下，合成方法都使用环状硫酸盐和中间体活化的氮丙啶的区域选择性开环。