4-pentenyl 4-O-β-D-galactopyranosyl-β-D-glucopyranoside | 153228-87-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 4-pentenyl 4-O-β-D-galactopyranosyl-β-D-glucopyranoside
• 英文别名: Pent-4-enyl β-D-lactoside；n-pentenyl (β-D-galactopyranosyl)-(1<*>4)-β-D-glucopyranoside；4-pentenyl β-D-galactopyranosyl-(1->4)-β-D-glucopyranoside；(2S,3R,4S,5R,6R)-2-[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-pent-4-enoxyoxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 153228-87-6
• 化学式: C₁₇H₃₀O₁₁
• 分子量: 410.419
• InChiKey: CZCQFXFYSHGMSP-BCKJCLKYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.7
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  179
• 氢给体数：
  7
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  4-pentenyl 4-O-β-D-galactopyranosyl-β-D-glucopyranoside 在 吡啶 、 三氯化铝 、 硼烷-三甲胺络合物 、 4 A molecular sieve 、 D(+)-10-樟脑磺酸 、 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 69.0h， 生成 n-pentenyl <6-O-(2-naphthylmethyl)-β-D-galactopyranosyl>-(1<*>4)-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of bi-fluorescence-labeled lactoside: A substrate for continual assay of ceramide glycanase

  摘要：

  A bi-fluorescence labeled derivative suitable for analysis of ceramide glycanase activity was constructed from 4-pentenyl lactoside. Selective modification of the galactosyl residue was attained by formation of 4',6'-naphthylmethylidene derivative, which was followed by regioselective reductive ring opening. The aglycon was extended by Michael addition of 2-aminoethanetiol, and dansylated at the terminal amino group. Excitation of the naphthyl group results in emission from the dansyl group, while the emission from the naphthyl group is quenched by the dansyl group. Upon digestion with ceramide glycanase, the energy transfer is severed and a decrease in the dansyl emission concommitant with an increase in the naphthyl emission was observed. This substrate was successfully used to analyze ceramide glycanase activity.

  DOI：

  10.1016/s0957-4166(00)80383-3
• 作为产物：
  描述：

  1',2',3',6',2,3,4,6-octa-O-acetyl-β-D-lactose 在 4 A molecular sieve 、 氢溴酸 、 碘 、 sodium methylate 、 乙酸酐 、 silver carbonate 作用下， 以 甲醇 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 35.0h， 生成 4-pentenyl 4-O-β-D-galactopyranosyl-β-D-glucopyranoside
  参考文献：
  名称：

  MBr1（globo-H）乳腺肿瘤抗原的第二代合成：正戊烯基糖苷方法在实现复杂糖蛋白连接方面的新应用。

  摘要：

  报道了六糖MBr1抗原（globo-H）的新合成。由于含有这种抗原的抗癌疫苗正进入前列腺癌的II期和III期临床试验，因此有必要对结构进行改进以提高效率。第二代合成的关键特征是制备globo-H作为其正戊烯基糖苷。该基团用作端基保护基和用作与载体蛋白生物缀合的接头。所得的合成物允许产生适当量的globo-H用于临床试验。

  DOI：

  10.1002/(sici)1521-3765(20000417)6:8<1366::aid-chem1366>3.0.co;2-k

文献信息

• Simple preparations of alkyl and cycloalkyl α-glycosides of maltose, cellobiose, and lactose
  作者：Shinkiti Koto、Motoko Hirooka、Takako Tashiro、Motokazu Sakashita、Masaharu Hatachi、Takayuki Kono、Miho Shimizu、Nahoko Yoshida、Sayaka Kurasawa、Natsuko Sakuma、Sunao Sawazaki、Akihiro Takeuchi、Naomi Shoya、Emi Nakamura

  DOI：10.1016/j.carres.2004.07.016

  日期：2004.10

  allyl, 4-pentenyl, and benzyl α-glycosides of maltose, cellobiose, and lactose were prepared (17–77% yield; α/β = 70/30–96/4) via a direct reaction of the free disaccharides with a binary AcBr–AcOH mixture, followed by glycosidation with alcohol using FeCl3 in MeNO2 or CH2Cl2, Zemplen deacetylation, and resolution of the anomeric mixture of glycosides by chromatography. Using MeCN as solvent for the

  摘要麦芽糖，纤维二糖和乳糖的烷基，环烷基，烯丙基，4-戊烯基和苄基α-糖苷的制备是（17-77％的收率；α/β= 70 / 30-96 / 4）。游离的二糖与二元AcBr-AcOH混合物混合，然后使用FeNO3在MeNO2或CH2Cl2中与酒精进行糖基化，Zemplen脱乙酰化，并通过色谱分离糖苷的异头混合物。使用MeCN作为糖苷化步骤的溶剂，还制备了相应的β-生物苷（16-61％产率；α/β= 25 / 75-5 / 95）。
• New Applications of the <i>n</i>-Pentenyl Glycoside Method in the Synthesis and Immunoconjugation of Fucosyl GM₁:  A Highly Tumor-Specific Antigen Associated with Small Cell Lung Carcinoma
  作者：Jennifer R. Allen、Samuel J. Danishefsky

  DOI：10.1021/ja992594f

  日期：1999.12.1

  to allow for smooth global deprotection. The synthesis and subsequent immunocharacterization served to confirm the assigned structure of the natural tumor antigen. Fully synthetic conjugate 1c advances our program toward the goal of using a synthetic vaccine containing fucosyl GM1 as a potential target for immune attack against small cell lung carcinoma.

  岩藻糖基 GM1 戊烯糖苷 1b 的合成及其与载体蛋白 KLH 的结合产生 1c 是相关的。使用包含在还原端正戊烯基糖苷 (NPG) 中的侧链烯烃实现 1b 的生物偶联。努力的关键步骤是使用我们的磺酰胺糖苷化方案进行立体特异性 [3 + 3] 偶联反应（参见 23 + 12 → 15）。需要预先安装 NPG 以获得最佳 [3 + 3] 耦合产量并允许平滑的全局脱保护。合成和随后的免疫表征用于确认天然肿瘤抗原的指定结构。完全合成的偶联物 1c 使我们的计划朝着使用含有岩藻糖基 GM1 的合成疫苗作为免疫攻击小细胞肺癌的潜在目标的目标前进。
• Chemoenzymatic Synthesis of Globo‐series Glycosphingolipids and Evaluation of Their Immunosuppressive Activities
  作者：Pei‐Yun Chiang、Avijit K. Adak、Wei‐Lun Liang、Chen‐Yen Tsai、Hsin‐Kai Tseng、Jing‐Yan Cheng、Jih Ru Hwu、Alice L. Yu、Jung‐Tung Hung、Chun‐Cheng Lin

  DOI：10.1002/asia.202200403

  日期：2022.8.15

  glycosylation approach enables modular assembly of globo-series glycosphingolipids including Gb4, Gb5, SSEA-4, and Gbolo H using the common substrate β-lactosyl sphingosine, which facilitates modification of the ceramide backbone. The fatty acid chain lengths in Globo H ceramides have shown differences in immunosuppressive activities on T cells activation.

  一锅多酶糖基化方法能够使用共同底物 β-乳糖基鞘氨醇对包括 Gb4、Gb5、SSEA-4 和 Gbolo H 在内的 globo 系列鞘糖脂进行模块化组装，这有助于修饰神经酰胺骨架。Globo H 神经酰胺中的脂肪酸链长度显示出对 T 细胞活化的免疫抑制活性的差异。
• Synthesis of a carboxyl linker containing Pk trisaccharide
  作者：Shu-Yi Hsieh、Mi-Dan Jan、Laxmikant N. Patkar、Chien-Tien Chen、Chun-Cheng Lin

  DOI：10.1016/j.carres.2004.10.024

  日期：2005.1

  An efficient synthesis of a p(k) trisaccharide with a functionalized side arm at the reducing end for conjugation to other molecules is presented. Construction of the pk trisaccharide with a high alpha-selectivity was achieved in high yield by coupling a reactive galactosyl phosphite donor with a lactosyl acceptor. (C) 2004 Elsevier Ltd. All rights reserved.
• O-Isopropylidenation of carbohydrates catalyzed by vanadyl triflate
  作者：Chun-Cheng Lin、Mi-Dan Jan、Shiue-Shien Weng、Chang-Ching Lin、Chien-Tien Chen

  DOI：10.1016/j.carres.2006.04.001

  日期：2006.8

  Vanadyl triflate has been identified as a mild and efficient catalyst for the chemoselective O-isopropylidenation of functionalized carbohydrates with acetone and acetone equivalents. The current protocol is compatible with a diverse array of protecting groups and the products can be readily isolated by simple aqueous wash. (c) 2006 Elsevier Ltd. All rights reserved.