4-O-(2-acetamido-2-deoxy-3,4-O-isopropylidene-β-D-talopyranosyl)-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal | 263845-22-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-O-(2-acetamido-2-deoxy-3,4-O-isopropylidene-β-D-talopyranosyl)-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal
• 英文别名: N-[(3aR,4R,6S,7S,7aR)-6-[(R)-[(4S,5R)-5-(dimethoxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methoxy]-4-(hydroxymethyl)-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-yl]acetamide
• CAS: 263845-22-3
• 化学式: C₂₅H₄₃NO₁₂
• 分子量: 549.616
• InChiKey: AZMSQUNVLRYOAY-HXRBIADQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  38
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  142
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  4-O-(2-acetamido-2-deoxy-3,4-O-isopropylidene-β-D-talopyranosyl)-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal 在 氢氧化钾 、 18-冠醚-6 、 溶剂黄146 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.95h， 生成 4-O-(2-acetamido-6-O-benzyl-2-deoxy-β-D-talopyranosyl)-2,3-O-isopropylidene-aldehydo-D-glucose dimethyl acetal
  参考文献：
  名称：

  通过高立体选择性β-D-Galptoβ-D-ManNAcp转化法从乳糖中制备二糖β-D-ManNAcp-（1→4）-D-Glc新方法

  摘要：

  摘要从4-O-（2-乙酰氨基-2-脱氧- 3,4-O-异亚丙基-6-O-三苯甲基-β-D-talopyranosyl）-2,3：5,6-二-O-异亚丙基-醛-D-葡萄糖二甲基乙缩醛2，得自6'-O三苯甲基三丙酮半乳糖二甲基乙缩醛，如先前报道[Barili，PL; Berti，G .；卡特拉尼（G. Catelani）；达安德里亚（D'Andrea）Puccioni，L.从乳糖立体合成4-O-（2-乙酰氨基-2-脱氧-β-D-talopyranosyl）-D-葡萄糖衍生物。J.碳水化合物。化学 [2000，19，79–81。]将β-D-塔洛糖胺单元上的保护基团初步修饰为3'，6'-di-O-苄基衍生物6，一种新的C-4'差向异构立体选择方案，该方案采用（a）区域选择性脱水，通过与NaH-磺酰基二咪唑系统同时活化-消除反应，提供4'-deoxy-hex-3'-eno衍生物7，（b）其区域和立体

  DOI：

  10.1081/car-200030011
• 作为产物：
  描述：

  4-O-(2-acetamido-2-deoxy-3,4-O-isopropylidene-6-O-trityl-β-D-talopyranosyl)-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal 在 三氯化铁 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以77%的产率得到4-O-(2-acetamido-2-deoxy-3,4-O-isopropylidene-β-D-talopyranosyl)-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal
  参考文献：
  名称：

  通过高立体选择性β-D-Galptoβ-D-ManNAcp转化法从乳糖中制备二糖β-D-ManNAcp-（1→4）-D-Glc新方法

  摘要：

  摘要从4-O-（2-乙酰氨基-2-脱氧- 3,4-O-异亚丙基-6-O-三苯甲基-β-D-talopyranosyl）-2,3：5,6-二-O-异亚丙基-醛-D-葡萄糖二甲基乙缩醛2，得自6'-O三苯甲基三丙酮半乳糖二甲基乙缩醛，如先前报道[Barili，PL; Berti，G .；卡特拉尼（G. Catelani）；达安德里亚（D'Andrea）Puccioni，L.从乳糖立体合成4-O-（2-乙酰氨基-2-脱氧-β-D-talopyranosyl）-D-葡萄糖衍生物。J.碳水化合物。化学 [2000，19，79–81。]将β-D-塔洛糖胺单元上的保护基团初步修饰为3'，6'-di-O-苄基衍生物6，一种新的C-4'差向异构立体选择方案，该方案采用（a）区域选择性脱水，通过与NaH-磺酰基二咪唑系统同时活化-消除反应，提供4'-deoxy-hex-3'-eno衍生物7，（b）其区域和立体

  DOI：

  10.1081/car-200030011

文献信息

• Stereoselective Synthesis of 4-<i>O</i>-(2-Acetamido-2-Deoxy-β-D-Talopyranosyl)-D-Glucose Derivatives from Lactose
  作者：Pier Luigi Barili、Giancarlo Berti、Giorgio Catelani、Felicia D'Andrea、Leonardo Puccioni

  DOI：10.1080/07328300008544066

  日期：2000.1

  The 6-O-trityl derivative of 2,3:5,6:3',4'-O-isopropylidenelactose dimethyl acetal (1) was converted through an oxidation/oximation/reduction sequence involving the free 2-OH group of the D-galactose moiety into the protected disaccharide 5 in up to 75% yield. The complete deprotection of 5 produced the disaccharide 4-O-(2-acetamido-2-deoxy-beta-D-talopyranosy)-D-glucose glucose (7a). The oxime LiAlH4 reduction step produced some unexpected side-products, the most abundant of which, the dimethyl acetal 9, deriving from cleavage of the D-glucose moiety, was formed only when the reaction was conducted in refluxing THF, but not when Et2O was used as the solvent.
• Improved Preparation of β‐<scp>d</scp>‐ManNAc‐(1→4)‐<scp>d</scp>‐Glc and β‐<scp>d</scp>‐TalNAc‐(1→4)‐<scp>d</scp>‐Glc Disaccharides and Evaluation of Their Activating Properties on the Natural Killer Cells NKR‐P1 and CD69 Receptors
  作者：Emanuele Attolino、Filippo Bonaccorsi、Giorgio Catelani、Felicia D'Andrea、Karel Křenek、Karel Bezouška、Vladimir Křen

  DOI：10.1080/07328300802030845

  日期：2008.6

  The synthetic access of either beta-D-ManNAc-(1-->4)-D-Glc (5) is beta-d-TalNAc-(1-->4)-D-Glc (6) disaccharides has been effectively improved with respect to previous syntheses (J. Carbohydr. Chem. 2000, 19, 79-91 and 2004, 23, 179-190), optimizing the preparation of suitably protected 4-O-(2-acetamido-2-deoxy-3,4-O-isopropylidene-beta-D-talopyranosyl)-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal derivatives obtained by complete stereoselective LiAlH4 reduction of new 2'-oximino precursors derived from lactose. The affinity of the disaccharides 5 and 6 toward the natural killer cell NKR-P1 and CD69 receptors has been evaluated and discussed.
• A New Preparation of the Disaccharide β‐<scp>D</scp>‐ManNAc<i>p</i>‐(1 → 4)‐<scp>D</scp>‐Glc from Lactose Through a Highly Stereoselective β‐<scp>D</scp>‐Gal<i>p</i>to β‐<scp>D</scp>‐ManNAc<i>p</i>Transformation
  作者：Emanuele Attolino、Giorgio Catelani、Felicia D'Andrea、Maria Nicolardi

  DOI：10.1081/car-200030011

  日期：2004.12.29

  Abstract A new method for the construction of the β‐D‐ManNAcp‐(1 → 4)‐D‐Glc framework from lactose avoiding the β‐mannosaminylation step was developed starting from 4‐O‐(2‐acetamido‐2‐deoxy‐3,4‐O‐isopropylidene‐6‐O‐trityl‐β‐D‐talopyranosyl)‐2,3:5,6‐di‐O‐isopropylidene‐aldehydo‐D‐glucose dimethyl acetal 2, obtained from 6′‐O‐trityl‐triacetonelactose dimethyl acetal, as previously reported [Barili, P

  摘要从4-O-（2-乙酰氨基-2-脱氧- 3,4-O-异亚丙基-6-O-三苯甲基-β-D-talopyranosyl）-2,3：5,6-二-O-异亚丙基-醛-D-葡萄糖二甲基乙缩醛2，得自6'-O三苯甲基三丙酮半乳糖二甲基乙缩醛，如先前报道[Barili，PL; Berti，G .；卡特拉尼（G. Catelani）；达安德里亚（D'Andrea）Puccioni，L.从乳糖立体合成4-O-（2-乙酰氨基-2-脱氧-β-D-talopyranosyl）-D-葡萄糖衍生物。J.碳水化合物。化学 [2000，19，79–81。]将β-D-塔洛糖胺单元上的保护基团初步修饰为3'，6'-di-O-苄基衍生物6，一种新的C-4'差向异构立体选择方案，该方案采用（a）区域选择性脱水，通过与NaH-磺酰基二咪唑系统同时活化-消除反应，提供4'-deoxy-hex-3'-eno衍生物7，（b）其区域和立体