methyl O--(2->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside | 125288-74-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl O--(2->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside
• 英文别名: methyl [methyl (5-acetamido-4,7,8,9-tetra-O-benzyl-3,5-dideoxy-D-glycero-D-galacto-2-nonulpyranosid)onate]-α-(2,6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside；methyl (2R,4S,5R,6R)-5-acetamido-2-[[(2R,3R,4S,5R,6S)-6-methoxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]methoxy]-4-phenylmethoxy-6-[(1S,2R)-1,2,3-tris(phenylmethoxy)propyl]oxane-2-carboxylate
• CAS: 125288-74-6
• 化学式: C₆₈H₇₅NO₁₄
• 分子量: 1130.34
• InChiKey: ZWCKZADSRDWHRQ-SNWNPUIDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.27
• 重原子数：
  83.0
• 可旋转键数：
  30.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  156.93
• 氢给体数：
  1.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  methyl O--(2->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 生成 methyl (2R,4S,5R,6R)-5-acetamido-4-hydroxy-2-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]methoxy]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate
  参考文献：
  名称：

  An efficient approach to streoselective glycosylation of N-acetylneuraminic acid: Used of phenylselenyl group as a stereocontrolling auxillary

  摘要：

  DOI：

  10.1016/s0040-4039(00)61852-x
• 作为产物：
  描述：

  methyl 5-acetamido-4,7,8,9-tetra-O-benzyl-3-bromo-3,5-dideoxy-D-erythro-L-manno-2-nonulopyranosonate 在 四氯化碳 、 偶氮二异丁腈 、 4 A molecular sieve 、 三苯基氢化锡 、 potassium tert-butylate 、 氰化汞 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 mercury dibromide 、 三(二甲胺基)膦 作用下， 以 四氢呋喃 、 四氯化碳 、 甲苯 、 叔丁醇 为溶剂， 反应 40.0h， 生成 methyl O--(2->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  Highly stereoselective glycosylation of N-acetylneuraminic acid aided by a phenylthio substituent as a stereocontrolling auxilliary

  摘要：

  DOI：

  10.1016/s0040-4039(00)80400-1

文献信息

• Highly stereoselective glycosylation of sialic acid aided by stereocontrolling auxiliaries
  作者：Yukishige Ito、Tomoya Ogawa

  DOI：10.1016/s0040-4020(01)97586-6

  日期：1990.1

  .alpha.-Selective glycosylation of sialic acid was achieved by using a sialic acid donor which carries a stereocontrolling auxiliary such as selenide or sulfide group at C-3 position.
• Per-<i>O</i>-Benzylated Ethyl 5-<i>N</i>-Acetyl-α-thiosialoside as a Glycosyl Donor for α-Silylation
  作者：Mei Xiao、Na Lei、Yongliang Zhang、Zhenni Huo、Dahai Ding、Jian Gao、Zhongwu Guo、Guofeng Gu、Feng Cai

  DOI：10.1080/07328303.2018.1508589

  日期：2018.7.24

  Per-O-benzylated ethyl 5-N-acetyl--thiosialoside 1 was synthesized and its reactivity as a sialyl donor was investigated. It was demonstrated that the reactions of 1 with various primary and secondary alcohol acceptors, including monosaccharides, gave good to excellent yields (53-92%) and acceptable to excellent -selectivity (:=2 approximate to 10:1) , showing its promise for application to sialoglycan synthesis.
• ITO, YUKISHIGE;OGAWA, TOMOYA, TETRAHEDRON, 46,(1990) N, C. 89-102
  作者：ITO, YUKISHIGE、OGAWA, TOMOYA

  DOI：——

  日期：——