(R)-2-(((4aR,6S,7R,8R,8aS)-7-acetamido-6-(benzyloxy)-2,2-dimethylhexahydropyrano[3,2-d][1,3]dioxin-8-yl)oxy)propanoic acid | 69323-67-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: (R)-2-(((4aR,6S,7R,8R,8aS)-7-acetamido-6-(benzyloxy)-2,2-dimethylhexahydropyrano[3,2-d][1,3]dioxin-8-yl)oxy)propanoic acid
• 英文别名: Benzyl 2-Acetamido-3-O-<(R)-1-carboxyethyl>-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranoside；benzyl 2-acetamido-3-O-(D-1-carboxyethyl)-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranoside；Benzyl 2-Acetamido-3-O-((R)-1-carboxyethyl)-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranoside；(2R)-2-[[(4aR,6S,7R,8R,8aS)-7-acetamido-2,2-dimethyl-6-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl]oxy]propanoic acid
• CAS: 69323-67-7
• 化学式: C₂₁H₂₉NO₈
• 分子量: 423.463
• InChiKey: FSTPIAWBNDKLRF-CAXYJRAJSA-N

物化性质

• 沸点：
  641.5±55.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.44
• 重原子数：
  30.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  (R)-2-(((4aR,6S,7R,8R,8aS)-7-acetamido-6-(benzyloxy)-2,2-dimethylhexahydropyrano[3,2-d][1,3]dioxin-8-yl)oxy)propanoic acid 在 Amberlite IR 120(H⁽¹⁺⁾) resin 作用下， 生成 benzyl 2-acetamido-2-deoxy-6-O-mesyl-3-O--4-O-(tetrahydropyran-2-yl)-α-D-glucopyranoside
  参考文献：
  名称：

  N-乙酰基-6-氨基-和-6-（酰基氨基）-6-脱氧muramoyl二肽的合成及其免疫佐剂活性。

  摘要：

  DOI：

  10.1016/s0008-6215(00)85146-0
• 作为产物：
  描述：

  D-GlcNAc 在 盐酸 、 sodium hydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 丙酮 为溶剂， 反应 34.0h， 生成 (R)-2-(((4aR,6S,7R,8R,8aS)-7-acetamido-6-(benzyloxy)-2,2-dimethylhexahydropyrano[3,2-d][1,3]dioxin-8-yl)oxy)propanoic acid
  参考文献：
  名称：

  Convergent Synthesis of Novel Muramyl Dipeptide Analogues: Inhibition of Porphyromonas gingivalis-Induced Pro-inflammatory Effects by High Doses of Muramyl Dipeptide

  摘要：

  Porphyromonas gingivalis (P.g.)-induced TNF-alpha can be affected by muramyl dipeptide (MDP) in a biphasic concentration-dependent manner. We found that in P.g.-exposed macrophages, treatment with 10 mu g/mL of MDP (MDP-low) up-regulated TNF-alpha by 29%, while 100 mu g/mL or higher (MDP-high) significantly decreased it (16% to 38%). MDP-high was found to affect the ubiquitin-editing enzyme A20 and activator protein 1 (AP1). An AP1 binding site was found in the promoter region of A20. A20 promoter activity was up-regulated after transfection of AP1 cDNA in cells. Four analogues of MDP (3-6) were prepared through a convergent strategy involving the synthesis of two unique carbohydrate fragments, 7a and 7b, using the peptide coupling reagents, EDCI and HOAt. Analogue 4 improved MDP function and P.g.-induced activities. We propose a new signaling pathway for TNF-alpha induction activated after exposing macrophages to both P.g. and MDP-high or analogue 4.

  DOI：

  10.1021/acs.jmedchem.6b00681

文献信息

• Synthesis of β(1–4)-Linked Disaccharides of<i>N</i>-Acetylglucosamine and<i>N</i>-Acetylmuramic Acid by Their Direct Condensation
  作者：Shoichi Kusumoto、Masahiro Imoto、Tsuyoshi Ogiku、Tetsuo Shiba

  DOI：10.1246/bcsj.59.1419

  日期：1986.5

  As a basic study in the synthetic approach to immunoactive cell wall peptidoglycan whose backbone is a β(1–4)-linked saccharide of alternating glucosamine and muramic acid, methods for the direct condensation of these sugar components were studied and O-(N-acetyl-β-muramyl)-(1→4)-N-acetyl-d-glucosamine and O-(N-acetyl-β-d-glucosaminyl)-(1→4)-N-acetylmuramic acid were synthesized. In the synthesis of the latter disaccharide, previous formation of an ester bond between the carboxyl group of muramic acid and the 6-hydroxyl group of glucosamine proved to facilitate the glycoside bond fromation between these sugar moieties.

  作为免疫活性细胞壁肽聚糖合成方法的一项基础研究，肽聚糖的骨架是由氨基葡萄糖和氨甲酰氨基葡萄糖交替组成的β(1-4)连接糖、研究人员研究了直接缩合这些糖成分的方法，并合成了 O-(N-乙酰基-β-木糖基)-(1→4)-N-乙酰基-d-葡糖胺和 O-(N-乙酰基-β-d-葡糖胺基)-(1→4)-N-乙酰基木糖酸。在合成后一种双糖时，事实证明，事先在苎麻酸的羧基和葡糖胺的 6-羟基之间形成的酯键有利于这些糖分子之间的糖苷键离化。
• Synthesis of C(6)-carboxylate analogs of N-acetylmuramic acid
  作者：Scott J. Hecker、Martha L. Minich

  DOI：10.1021/jo00311a026

  日期：1990.11
• YAMAMURA, YUITI;XASEHGAVA, AKIRA;ADZUMA, SIRO;KOBAYASI, SAKAEH
  作者：YAMAMURA, YUITI、XASEHGAVA, AKIRA、ADZUMA, SIRO、KOBAYASI, SAKAEH

  DOI：——

  日期：——
• YAMAMURA, YUICHI;HASEGAWA, AKIRA;AZUMA, ICHIRO;KOBAYASHI, SHIGERU
  作者：YAMAMURA, YUICHI、HASEGAWA, AKIRA、AZUMA, ICHIRO、KOBAYASHI, SHIGERU

  DOI：——

  日期：——