5-acetamido-4,7,8,9-tetra-O-benzyl-2,3-dehydro-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonic acid | 125288-69-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-acetamido-4,7,8,9-tetra-O-benzyl-2,3-dehydro-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonic acid
• 英文别名: (2R,3R,4S)-3-acetamido-4-phenylmethoxy-2-[(1S,2R)-1,2,3-tris(phenylmethoxy)propyl]-3,4-dihydro-2H-pyran-6-carboxylic acid
• CAS: 125288-69-9
• 化学式: C₃₉H₄₁NO₈
• 分子量: 651.756
• InChiKey: NXEGUXLNLKJLNJ-VUCFBZHLSA-N

物化性质

• 沸点：
  833.7±65.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.83
• 重原子数：
  48.0
• 可旋转键数：
  17.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  112.55
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  5-acetamido-4,7,8,9-tetra-O-benzyl-2,3-dehydro-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonic acid 在 palladium on activated charcoal 吡啶 、 4-二甲氨基吡啶 、 偶氮二异丁腈 、 二乙胺基三氟化硫 、 三氟甲磺酸三甲基硅酯 、 氢气 、 三正丁基氢锡 、 sodium methylate 、 silver(I) acetate 、 三正丁基锡三氟基磺酸盐 作用下， 以 甲醇 、 四氯化碳 、 乙醚 、 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 47.75h， 生成 1,2;3,4-Di-O-isopropyliden-6-O-(methyl-5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-didesoxy-D-glycero-α-D-galacto-2-nonulopyranosylonat)-α-D-galactopyranose
  参考文献：
  名称：

  Highly stereoselective glycosylation of sialic acid aided by stereocontrolling auxiliaries

  摘要：

  .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.

  DOI：

  10.1016/s0040-4020(01)97586-6
• 作为产物：
  描述：

  methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate 在 氢氧化钾 、 sodium methylate 、 四丁基碘化铵 、 barium(II) oxide 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 生成 5-acetamido-4,7,8,9-tetra-O-benzyl-2,3-dehydro-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonic acid
  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

文献信息

• A new strategy for stereoselective synthesis of sialic acid-containing glycopeptide fragment
  作者：Zhi-Guang Wang、Xu-Fang Zhang、Yukishige Ito、Yoshiaki Nakahara、Tomoya Ogawa

  DOI：10.1016/s0968-0896(96)00172-1

  日期：1996.11

  Sialic acid donor 5, which has a thiophenyl group as a stereocontrolling auxiliary and thiomethyl group as a leaving group was prepared and subjected to model glycosylation. Reactions with acceptor substrates 6, 7, and 8 gave coupled products 9b, 10b, and 11b, respectively, in a higher efficiency than previously observed for the bromide la. This reaction was further applied to the synthesis of protected glyco-amino acid fragment 12, that is strategically designed for the synthesis of sialic acid containing glycopeptides. Copyright (C) 1996 Elsevier Science Ltd
• ITO, YUKISHIGE;OGAWA, TOMOYA, TETRAHEDRON, 46,(1990) N, C. 89-102
  作者：ITO, YUKISHIGE、OGAWA, TOMOYA

  DOI：——

  日期：——