1-O-methyl 3,5-di-O-benzyl β(D)xylo-pentoaldofuranose | 79083-39-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-O-methyl 3,5-di-O-benzyl β(D)xylo-pentoaldofuranose
• 英文别名: 1-O-methyl-3,5-di-O-benzyl-β-D-xylofuranose；methyl 3,5-di-O-benzyl-β-D-xylofuranoside；(2R,3R,4R,5R)-2-methoxy-4-phenylmethoxy-5-(phenylmethoxymethyl)oxolan-3-ol
• CAS: 79083-39-9
• 化学式: C₂₀H₂₄O₅
• 分子量: 344.408
• InChiKey: SOWIHMANTOCUNZ-YSTOQKLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-O-methyl 3,5-di-O-benzyl β(D)xylo-pentoaldofuranose 在 trityl tetrafluoroborate 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以89%的产率得到1,2-anhydro-3,5-di-O-benzyl-α-D-xylofuranose
  参考文献：
  名称：

  Mild and Efficient Chemoselective Deprotection of Anomeric O-Methyl Glycosides with Trityl Tetrafluoroborate

  摘要：

  A facile chemoselective deprotection of anomeric O-methyl glycosides has been achieved in good to excellent yields within 10-40 min with use of trityl tetrafluoroborate in dichloromethane at ambient temperatures. The present method is easily implemented and tolerates different functional groups.

  DOI：

  10.1021/jo800693w
• 作为产物：
  描述：

  1,2:3,5-双-O-异亚丙基-alpha-D-呋喃木糖 在 氢氧化钾 、 硫酸 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 55.0h， 生成 1-O-methyl 3,5-di-O-benzyl β(D)xylo-pentoaldofuranose
  参考文献：
  名称：

  Aminonuclosides and Their Derivatives; XII¹. A New Synthesis of 1-O-Methyl-3-azido-2,3-dideoxy-D-ribofuranose

  摘要：

  DOI：

  10.1055/s-1984-31038

文献信息

• A convenient method for deuteration at the alpha position of an oxo group in carbohydrates
  作者：Ahmed El Nemr、Tsutomu Tsuchiya

  DOI：10.1016/s0040-4039(98)00539-5

  日期：1998.5

  CH-Hydrogens at the alpha position of an oxo group in carbohydrates are readily exchanged in 4:4:2:3 1,4-dioxane-THF-Et3N-D2O.

  碳水化合物中一个羰基的α位上的CH-氢很容易在4：4：2：3 1,4-二恶烷-THF-Et 3 N-D 2 O中交换。
• A facile synthesis of 1,2-anhydroglycofuranose benzyl ethers
  作者：Yuguo Du、Fanzuo Kong

  DOI：10.1016/0040-4039(94)02311-x

  日期：1995.1

  The synthesis of 1,2-anhydromanno-, -lyxo-, -gluco-, and -xylofuranose benzyl ethers was successfully achieved via intramolecular reaction of the corresponding C-1 alkoxide with C-2 bearing tosyloxy group. The key intermediates, furanose 2-sulfonates, were prepared from the corresponding 1,2-diols and tosyl chloride under phase transfer condition in good yields.

  通过相应的C-1醇盐与带有甲苯磺酰氧基的C-2的分子内反应，成功地完成了1,2-脱水甘露糖基-，-lyxo-，-葡萄糖-和-xylofuranose苄基醚的合成。在相转移条件下，由相应的1,2-二醇和甲苯磺酰氯制备了关键中间体呋喃糖2-磺酸盐，收率很高。
• Direct α-Selective Glycosylations of Acetyl-Protected 2-Deoxy- and 2,6-Dideoxythioglycosides by Preactivation Protocol
  作者：Xin-Shan Ye、Yin-Suo Lu、Qin Li、Yuan Wang

  DOI：10.1055/s-0029-1219943

  日期：2010.6

  An efficient preactivation protocol for the highly α-stereo-selective glycosylation of2-deoxy- and 2,6-dideoxysugars has been developed using acetyl-protected 2-deoxy- and 2,6-dideoxythioglycosides as glycosyl donors. The approach allows a wide range of glycosyl acceptors and donors to be used.

  使用乙酰保护的 2-脱氧-和 2,6-双脱氧硫糖苷作为糖基供体，开发了一种用于 2-脱氧-和 2,6- 双脱氧糖的高度 α-立体选择性糖基化的有效预活化方案。该方法允许使用范围广泛的糖基受体和供体。
• Highly Direct α-Selective Glycosylations of 3,4-<i>O</i>-Carbonate-Protected 2-Deoxy- and 2,6-Dideoxythioglycosides by Preactivation Protocol
  作者：Yin-Suo Lu、Qin Li、Li-He Zhang、Xin-Shan Ye

  DOI：10.1021/ol801190c

  日期：2008.8.21

  A new efficient pre-activation method for the highly alpha-stereoselective glycosylation of 2-deoxysugars and 2,6-dideoxysugars has been developed using 2-deoxy- and 2,6-dideoxythioglycosides as glycosyl donors. The approach allows a wide range of glycosyl acceptors and donors to be used; the alpha-selectivity is very good to excellent.

  使用2-脱氧和2,6-二脱氧硫代糖苷作为糖基供体，已经开发出一种用于2-脱氧糖和2,6-二脱氧糖的高度α-立体选择性糖基化的新的有效预活化方法。该方法允许使用广泛的糖基受体和供体。alpha选择性非常好，甚至非常好。
• The Use of Grignard Reagents in the Synthesis of Carbohydrates. III. The One-way Anomerization of Methyl Glycofuranosides and the Opening of Their Furanose Rings
  作者：Masajiro Kawana、Hiroyoshi Kuzuhara、Sakae Emoto

  DOI：10.1246/bcsj.54.1492

  日期：1981.5

  The anomerization of methyl glycofuranoside derivatives with methylmagnesium iodide or t-butylmagnesium bromide occurred in a one-way manner. For example, methyl 5-O-benzyl-β-D-ribofuranoside (3β) was converted into the corresponding α-anomer (3α) in a 95% yield when a mixture of 3β and t-butylmagnesium bromide in benzene–ether was heated at about 75 °C to remove the ether; the reverse reaction (from

  甲基呋喃糖苷衍生物与甲基碘化镁或叔丁基溴化镁的异构化以单向方式发生。例如，当 3β 和叔丁基溴化镁在苯-醚中的混合物加热时，甲基 5-O-苄基-β-D-呋喃核糖苷 (3β) 以 95% 的产率转化为相应的 α-异头物 (3α)在约 75°C 下除去乙醚；逆反应（从3α到（3β）没有进行。3β与甲基碘化镁反应得到开链产物（33%），除3α（30%）外，还测试了20种异头异构体，并对其作用机理进行了研究。在反应过程中也观察到用格氏试剂裂解苄基或三苯甲基保护基团。