Methyl 4-azido-4,6-dideoxy-2,3-di-O-4-methoxybenzyl-α-D-mannopyranoside | 172603-66-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methyl 4-azido-4,6-dideoxy-2,3-di-O-4-methoxybenzyl-α-D-mannopyranoside
• 英文别名: (2S,3S,4S,5R,6R)-5-azido-2-methoxy-3,4-bis[(4-methoxyphenyl)methoxy]-6-methyloxane
• CAS: 172603-66-6
• 化学式: C₂₃H₂₉N₃O₆
• 分子量: 443.5
• InChiKey: YNJIILFAILJBPF-LNMYJNIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Methyl 4-azido-4,6-dideoxy-2,3-di-O-4-methoxybenzyl-α-D-mannopyranoside 在 吡啶 、 硫化氢 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (S)-2-Phenyl-[1,3]dioxane-4-carboxylic acid [(2R,3R,4S,5S,6S)-6-methoxy-4,5-bis-(4-methoxy-benzyloxy)-2-methyl-tetrahydro-pyran-3-yl]-amide
  参考文献：
  名称：

  衍生自3-脱氧-1-甘油-tetronic酸的新型N-酰化试剂1

  摘要：

  用三氟乙酸处理市售的N - Boc -4- O-苄基-1-高丝氨酸，然后将相应的N-脱保护的衍生物脱氨，得到4 - O-苄基-3-脱氧-1-甘油-四氢代酸。 （5）。在保护4-位的3-脱氧-1-甘油-四氢代酸的另一种方法中，L-苹果酸中的羧基被还原，并且所得的三醇被亚苄基化。在t存在下氧化与CrO 3-吡啶配合物形成的2,4- O-亚苄基衍生物丁基醇，得到吨丁基2,4- ø -亚苄基-3-脱氧升-甘油基-tetronate（13）。在Na +交换H +后，将后者用氢氧化钠水溶液皂化，得到2，4 - O-亚苄基-3-脱氧-1-甘油-四氢代酸（15）。在13中打开乙缩醛环，然后将叔丁酯官能团水解裂解，得到的材料与以原始方式获得的5没有区别。当测试它们的N效率时对D-过胺的衍生物进行酰化，酸5和15均以高收率得到了相应的四氢酰胺基衍生物。

  DOI：

  10.1080/07328309608005668
• 作为产物：
  描述：

  甲基 4-叠氮基-4,6-二脱氧吡喃甘露糖苷 、 4-甲氧基氯苄 在 sodium hydroxide 、 四丁基溴化铵 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以13%的产率得到Methyl 4-azido-4,6-dideoxy-2,3-di-O-4-methoxybenzyl-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis and crystal structure of methyl 4,6-dideoxy-4-(3-deoxy-l-glycero-tetronamido) - 2-O-methyl-α-d-mannopyranoside, the methyl α-glycoside of the terminal unit, and presumed antigenic determinant, of the O-specific polysaccharide of Vibrio cholerae O:1, serotype Ogawa

  摘要：

  Methyl 4-azido-4,6-dideoxy-3-O-benzyl-alpha-D-mannopyranoside and its analogous 3-O-(4-methoxybenzyl) derivative were methylated and the 2-O-methyl derivatives formed were converted into methyl 4-amino-4,6-dideoxy-2-O-methyl-alpha-D-mannopyranoside. Reaction of the latter with 3-deoxy-L-glycero-tetronolactone gave the methyl glycoside of 4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-2-O-methyl-alpha-D-mannopyranose, the monosaccharide that is reported to be the terminal moiety of the O-specific polysaccharide of Vibrio cholerae 0:1, serotype Ogawa. The unit cell packing of the compound, which crystallized as a monohydrate, differs from that of the previously described crystalline compound lacking the 2-O-methyl group. The unmethylated sugar is the terminal moiety of the O-specific polysaccharide of Vibrio cholerae 0:1, serotype Inaba. The crystal structure of methyl 4,6-dideoxy-2-0-methyl-4-trifluoroacetamido-alpha-D-mannopyranoside is also described.

  DOI：

  10.1016/0008-6215(95)00147-l

文献信息

• New<i>N</i>-Acylating Reagents Derived from 3-Deoxy-<scp>l</scp>-<i>glycero</i>-tetronic Acid¹
  作者：Ping-sheng Lei、Yuji Ogawa、Pavol Kováč

  DOI：10.1080/07328309608005668

  日期：1996.5

  exchange for H+, 2,4-O-benzylidene-3-deoxy-l-glycero-tetronic acid (15). Opening of the acetal ring in 13, followed by hydrolytic cleavage of the t-butyl ester function gave material indistinguishable from 5 obtained in the original way. When tested for their efficiency of N-acylation of derivatives of D-perosamine, both acids 5 and 15 gave the corresponding tetronamido derivatives in high yields.

  用三氟乙酸处理市售的N - Boc -4- O-苄基-1-高丝氨酸，然后将相应的N-脱保护的衍生物脱氨，得到4 - O-苄基-3-脱氧-1-甘油-四氢代酸。 （5）。在保护4-位的3-脱氧-1-甘油-四氢代酸的另一种方法中，L-苹果酸中的羧基被还原，并且所得的三醇被亚苄基化。在t存在下氧化与CrO 3-吡啶配合物形成的2,4- O-亚苄基衍生物丁基醇，得到吨丁基2,4- ø -亚苄基-3-脱氧升-甘油基-tetronate（13）。在Na +交换H +后，将后者用氢氧化钠水溶液皂化，得到2，4 - O-亚苄基-3-脱氧-1-甘油-四氢代酸（15）。在13中打开乙缩醛环，然后将叔丁酯官能团水解裂解，得到的材料与以原始方式获得的5没有区别。当测试它们的N效率时对D-过胺的衍生物进行酰化，酸5和15均以高收率得到了相应的四氢酰胺基衍生物。
• Synthesis and crystal structure of methyl 4,6-dideoxy-4-(3-deoxy-l-glycero-tetronamido) - 2-O-methyl-α-d-mannopyranoside, the methyl α-glycoside of the terminal unit, and presumed antigenic determinant, of the O-specific polysaccharide of Vibrio cholerae O:1, serotype Ogawa
  作者：Ping-sheng Lei、Yuji Ogawa、Judith L. Flippen-Anderson、Pavol Kováĉ

  DOI：10.1016/0008-6215(95)00147-l

  日期：1995.9

  Methyl 4-azido-4,6-dideoxy-3-O-benzyl-alpha-D-mannopyranoside and its analogous 3-O-(4-methoxybenzyl) derivative were methylated and the 2-O-methyl derivatives formed were converted into methyl 4-amino-4,6-dideoxy-2-O-methyl-alpha-D-mannopyranoside. Reaction of the latter with 3-deoxy-L-glycero-tetronolactone gave the methyl glycoside of 4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-2-O-methyl-alpha-D-mannopyranose, the monosaccharide that is reported to be the terminal moiety of the O-specific polysaccharide of Vibrio cholerae 0:1, serotype Ogawa. The unit cell packing of the compound, which crystallized as a monohydrate, differs from that of the previously described crystalline compound lacking the 2-O-methyl group. The unmethylated sugar is the terminal moiety of the O-specific polysaccharide of Vibrio cholerae 0:1, serotype Inaba. The crystal structure of methyl 4,6-dideoxy-2-0-methyl-4-trifluoroacetamido-alpha-D-mannopyranoside is also described.