methyl (2,4,5,7,8,9-hexa-O-acetyl-3-deoxy-D-glycero-β-D-galacto-2-nonulopyran-ose)onate | 123843-50-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (2,4,5,7,8,9-hexa-O-acetyl-3-deoxy-D-glycero-β-D-galacto-2-nonulopyran-ose)onate
• 英文别名: methyl (2,4,5,7,8,9-hexa-O-acetyl-3-deoxy-D-glycero-β-D-galacto-2-nonulopyranosid)onate；methyl (hexa-O-acetyl-3-deoxy-α-D-glycero-D-galacto-2-nonulopyranosid)onate；methyl (2R,4S,5R,6R)-2,4,5-triacetyloxy-6-[(1R,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
• CAS: 123843-50-5
• 化学式: C₂₂H₃₀O₁₅
• 分子量: 534.471
• InChiKey: CDJOMBIWROBESK-QDRUEPRISA-N

物化性质

• 熔点：
  103-104 °C
• 沸点：
  540.5±50.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  37
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  193
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  methyl (2,4,5,7,8,9-hexa-O-acetyl-3-deoxy-D-glycero-β-D-galacto-2-nonulopyran-ose)onate 在 三氟甲磺酸三甲基硅酯 作用下， 以 乙腈 为溶剂， 以63%的产率得到甲基4,5-二-O-乙酰基-2,6-脱水-3-脱氧-6-(1,2,3-三乙酰氧基丙基)己-2-酮酸酯
  参考文献：
  名称：

  2,3-Didehydro-2-deoxysialic acids structurally varied at C-5 and their behaviour towards the sialidase from Vibrio cholerae

  摘要：

  2,3-Didehydro-2-deoxy-N-trifluoroacetylneuraminic acid (5-trifluoroacetyl-Neu2en) (3) has been synthesised from Neu5Ac2en (1) by hydrazinolysis, to give Neu2en (2), followed by N-trifluoroacetylation. 2,3-Didehydro-2,3-dideoxy-D-glycero-D-galacto-2-nonulopyranoson ic acid (Kdn2en, 8) and 5-azido-2,3-didehydro-2,3,5-trideoxy-D-glycero-D-galacto-2-nonu lopyranosonic acid (5-azido-5-deoxy-Kdn2en, 9) have been prepared from the acetylated methyl esters of Kdn (4) and 5-azido-5-deoxy-Kdn (5) via Zemplén saponification. The behaviour of the above 2,3-didehydro-2-deoxysialic acids towards Vibrio cholerae sialidase has been investigated.

  DOI：

  10.1016/0008-6215(92)84150-q
• 作为产物：
  描述：

  (4S,5R)-2,2-dimethyl-5-[(1S,2R)-1,2,3-tris[[tert-butyl(dimethyl)silyl]oxy]propyl]-1,3-dioxolane-4-carbaldehyde 在 吡啶 、 4-二甲氨基吡啶 、 二甲基硫 、 Dowex 50W resin (H(+) form) 、 水 、 氯化铵 、 臭氧 、 三氟乙酸 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 45.53h， 生成 methyl (2,4,5,7,8,9-hexa-O-acetyl-3-deoxy-D-glycero-β-D-galacto-2-nonulopyran-ose)onate
  参考文献：
  名称：

  First total synthesis of (+)-3-deoxy-D-glycero-D-galacto-2-nonulosonic acid (KDN) from a non-carbohydrate source

  摘要：

  对映体纯顺式-1,2-二氢邻苯二酚 2 是通过微生物氧化氯苯得到的产物，通过十步反应顺序转化为 KDN 1。

  DOI：

  10.1039/a801889h

文献信息

• Stereoselective Synthesis of α-Keto-deoxy-D-glycero-D-galacto-nonulosonic Acid Glycosides by Means of the 4,5-O-Carbonate Protecting Group
  作者：David Crich、Chandrasekhar Navuluri

  DOI：10.1002/anie.200907178

  日期：——

  Unrivaled: A 1‐adamantyl thioglycoside derivative of the nonulosonic acid KDN, carrying a 4,5‐O‐carbonate protecting group, is a highly efficient and α‐selective KDN donor when activated using N‐iodosuccinimide (NIS) and trifluoromethanesulfonic acid (TfOH). Glycosylations conducted with this protecting group do not suffer from competing glycal formation.

  无与伦比的：非酮糖酸 KDN 的 1-金刚烷基硫糖苷衍生物，带有 4,5- O-碳酸酯保护基团，当使用N-碘代琥珀酰亚胺 (NIS) 和三氟甲磺酸 (TfOH ）。用该保护基团进行的糖基化不会受到竞争性糖基形成的影响。
• Facile Synthesis of 4-Acylamino-2,6-anhydro-2,3,4-trideoxy-D-glycero-D-galacto-non-2-enoic Acids.
  作者：Xue-Long SUN、Toshitsugu KAI、Makoto TANAKA、Hiroaki TAKAYANAGI、Kimio FURUHATA

  DOI：10.1248/cpb.43.1654

  日期：——

  The title compounds were synthesized from 3-deoxy-D-glycero-D-galacto-2-nonulosonic acid (5, KDN) by a new method which is similar to the Ritter reaction. The structures on these compounds were elucidated from the MS, elemental analysis, 1H-NMR and 13C-NMR, data, and the stereochemistry of methyl 4-benzoylamino-5, 7, 8, 9-tetra-O-acetyl-2, 6-anhydro-2, 3-dideoxy-D-glycero-D-galacto-non-2-enonate (13) was determined by X-ray crystallographic analysis.

  标题化合物是通过一种类似于Ritter反应的新方法从3-去氧-D-甘露糖-D-半乳糖-2-非烯醇酸（5，KDN）合成的。这些化合物的结构通过质谱、元素分析、1H-NMR和13C-NMR数据进行了解释，甲基4-苯甲酰氨基-5, 7, 8, 9-四-O-乙酰基-2, 6-脱水-2, 3-去氧-D-甘露糖-D-半乳糖-非-2-烯酸（13）的立体化学则通过X射线晶体学分析确定。
• Synthesis of 3-deoxy-D-manno-2-octulosonic acid (KDO) and its analogs based on KDO aldolase-catalyzed reactions
  作者：Takeshi Sugai、Gwo Jenn Shen、Yoshitaka Ichikawa、Chi Huey Wong

  DOI：10.1021/ja00055a008

  日期：1993.1

  3-Deoxy-D-manno-2-octulosonic acid (D-KDO) was synthesized from D-arabinose and pyruvate in 67% yield by using KDO aldolase (EC 4.1.2.21) from Aureobacterium barkerei strain KDO-37-2 (ATCC 49977). Studies on the substrate specificity of the enzyme with more than 20 natural and unnatural sugars indicate that this enzyme widely accepts trioses, tetroses, pentoses, and hexoses as substrates, especially

  3-脱氧-D-甘露糖-2-辛糖酸 (D-KDO) 使用来自巴氏金杆菌菌株 KDO-37-2 (ATCC) 的 KDO 醛缩酶 (EC 4.1.2.21) 从 D-阿拉伯糖和丙酮酸以 67% 的产率合成49977）。对该酶具有 20 多种天然和非天然糖的底物特异性的研究表明，该酶广泛接受丙糖、丁糖、戊糖和己糖作为底物，尤其是在 1 位具有 R 构型的酶。2位取代基对羟醛反应影响不大
• Sialyl aldolase in organic synthesis: from the trout egg acid 3-deoxy-D-glycero-D-galacto-2-nonulosonic acid (KDN) to branched-chain higher ketoses as possible new chirons.
  作者：Claudine Augé、Christine Gautheron、Serge David、Annie Malleron、Bertrand Cavayé、Bénédicte Bouxom

  DOI：10.1016/s0040-4020(01)97593-3

  日期：1990.1

  N-Acetylneuraminate pyruvate lyase accepts as substrates varied non-nitrogeneous sugars. Condensation of pyruvate with D-mannose yields 3-deoxy-D-glycero-D-galacto-2-nonulosonic acid (KDN) a component of rainbow trout egg polysialoglycoprotein. From some easily available monosaccharides were prepared other ulosonic acids: 3-deoxy-D-galacto-2-octulosonic 35dideoxy-D-gluco-2-nonulosonic and 37-dideo

  N-乙酰神经氨酸丙酮酸裂解酶接受各种非氮源糖作为底物。丙酮酸与D-甘露糖的缩合产生3-脱氧-D-甘油-D-半乳糖-2-壬基磺酸（KDN），它是虹鳟鱼卵多唾液酸糖蛋白的一种成分。从一些容易得到的单糖制备其它ulosonic酸：3-脱氧-D-半乳-2-辛酮糖35dideoxy-D-葡糖-2- nonulosonic和37二脱氧D-半乳-2- nonulosonic酸。葡萄糖不是良好的底物，D-阿拉伯糖产生了预期的3-脱氧-D-葡萄糖的混合物-2-辛基磺酸（19％）和3-脱氧-D-甘露糖-2-辛基磺酸（16％）。后者是来自细菌多糖的众所周知的糖酸KDO，其是由缩合步骤中的异常取向导致的。通过保留2-脱氧-2- C -2-苯基-D-的76％收率的转化，证明了酶对糖的C（2）处的取代基的性质的相对冷漠，只要保留了D-甘露聚糖构型即可。甘露糖转化成35-二脱氧-5 - C-苯基-D-葡萄糖-2-壬基磺
• Studies on sialic acids. XIII. Isolation of 3-deoxy-D-glycero-D-galacto-2-nonulopyranosonic acid (KDN) from chum salmon, Oncorhynchus keta.
  作者：Mitsunobu NAKAMURA、Kimio FURUHATA、Kiyoko YAMAZAKI、Haruo OGURA、Hisao KAMIYA、Hitoshi IDA

  DOI：10.1248/cpb.37.2204

  日期：——

  A method for analysis of 3-deoxy-D-glycero-D-galacto-2-nonulopyranosonic acid (KDN) by high-performance liquid chromatography (HPLC) with a strongly basic anion-exchange resin was developed. The method was applied to detect free KDN in water used to rinse of fertilized eggs of chum salmon, Oncorhynchus keta. Furthermore, KDN was isolated from the water as a fully protected derivative.

  采用强碱性阴离子交换树脂，建立了高效液相色谱法（HPLC）分析3-脱氧-D-甘油-D-半乳-2-壬磺吡喃糖酸（KDN）的方法。该方法用于检测大马哈鱼（Oncorhynchus keta）受精卵冲洗水中的游离 KDN。此外，还从水中分离出了 KDN 的完全保护衍生物。