四环[4.3.02,9.05,7]壬烷 | 74513-18-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 四环[4.3.02,9.05,7]壬烷
• 英文名称: n-dodecyl β-D-galactopyranosyl-(1->4)-β-D-glucopyranoside
• 英文别名: n-dodecyl β-D-lactoside；dodecyl-β-lactoside；Dodecyl 4-O-I(2)-D-galactopyranosyl-I(2)-D-glucopyranoside；(2S,3R,4S,5R,6R)-2-[(2R,3S,4R,5R,6R)-6-dodecoxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 74513-18-1
• 化学式: C₂₄H₄₆O₁₁
• 分子量: 510.623
• InChiKey: NLEBIOOXCVAHBD-ARYMTDNSSA-N

物化性质

• 熔点：
  106-111 °C(Solv: methanol (67-56-1))
• 沸点：
  703.5±60.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  35
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  179
• 氢给体数：
  7
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  1',2',3',6',2,3,4,6-octa-O-acetyl-β-D-lactose 在 molecular sieve 、 三氟化硼乙醚 、 sodium methylate 作用下， 以 甲醇 、 1,2-二氯乙烷 为溶剂， 反应 34.0h， 生成 四环[4.3.02,9.05,7]壬烷
  参考文献：
  名称：

  Effect of Anomeric Linkage on the Sialylation of Glycosides by Cells

  摘要：

  The synthesis of sialylated glycosides using saccharide primers and cells was investigated. alpha center dot and beta center dot Saccharide primers were chemically synthesized and introduced into B16 melanoma cells to prime oligosaccharide synthesis. Incorporation of alpha- and beta-dodecyl lactosides into B16 cells resulted in the sialylation of the galactose residue to give GM3-type oligosaccharides. The beta-dodecyl galactoside primer was sialylated but the alpha-dodecyl galactoside primer was not. Both the alpha- and beta-dodecyl glucoside primers were not elongated. In the glycosylation of primers by cells, this research confirmed that sialyl transferases tolerate acceptor modifications and are permissive to primer elongation regardless of the alpha- or beta-linkage to the aglycon unit. However, the presence of the terminal galactose residue that is beta-linked to the adjacent saccharide or aglycon unit is essential for sialylation by cellular enzymes to occur.

  DOI：

  10.1080/07328300500208107

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）。
• PROCESS FOR PRODUCING OLIGOSACCHARIDE CHAIN
  申请人：Keio University

  公开号：EP1384786A1

  公开（公告）日：2004-01-28

  The present invention relates to a method for producing oligosaccharides comprising giving saccharide primers to human cells, plant cells or yeast, and a method for producing oligosaccharides comprising giving saccharide primers to cells (excluding COS-7 cells) cultured using a high-density culturing method. The oligosaccharides are applicable to drugs, pharmaceuticals, diagnostic agents, sugar chain tips etc.

  本发明涉及一种生产低聚糖的方法，包括向人体细胞、植物细胞或酵母提供糖引物，以及一种生产低聚糖的方法，包括向采用高密度培养法培养的细胞（不包括 COS-7 细胞）提供糖引物。这些寡糖适用于药物、药品、诊断剂、糖链提示等。
• Process for producing oligosaccharide chains
  申请人：——

  公开号：US20040086981A1

  公开（公告）日：2004-05-06

  The present invention relates to a method for efficiently producing oligosaccharide for use in pharmaceutical drugs, medicals, glyco chips and the like from cells, said method comprising giving saccharide primers to human cells, plant cells, or yeast, or giving saccharide primers to cells cultured using a high-density culture method.

  本发明涉及一种从细胞中高效生产用于制药、医疗、糖芯片等的寡糖的方法，所述方法包括向人体细胞、植物细胞或酵母细胞提供糖引物，或向采用高密度培养法培养的细胞提供糖引物。
• PROCESS FOR PRODUCING OLIGOSACCHARIDE CHAINS
  申请人：GLYCOMEDICS, INC.

  公开号：EP1384786B1

  公开（公告）日：2010-01-27
• 5a-Carba-glycopyranoside primers: potential building blocks for biocombinatorial synthesis of glycosphingolipid analogues
  作者：Hiroshi Aoyama、Seiichiro Ogawa、Toshinori Sato

  DOI：10.1016/j.carres.2009.06.029

  日期：2009.10

  Three ether-linked alkyl 5a-carba-glycopyranosides 1b,d, and 5b, and 5a'-carba-lactoside 7b were examined as potent primers in mouse 1316 melanoma cells for their feasibility as building blocks for oligosaccharide biosynthesis. Uptake by B16 cells was first observed for all carba-glycoside primers, and, especially, the 5a-carba-sugar analogues of N-acetyl-beta-D-glucosaminide 1b and beta-D-glucoside 1d were shown to produce two-to-four-fold larger amounts of glycosylated products than the corresponding true sugar primers 1a and 1c. The carba glycoside uptake by cells resulted in beta-galactosylation and subsequent sialylation of the incorporated galactose residues, giving rise to glycosylated products 3b and 3d having similar glycan structures as the ganglioside GM3. According to efficient uptake in cells, in addition to stability of the ether-linked pseudo-reducing ends of the oligosaccharides that formed, the carba glycoside primers have been demonstrated to be versatile building blocks for these biocombinatorial syntheses of glycolipid oligosaccharide mimetics. On the other hand, uptake for 5a-carba-galactopyranoside residue was found to be decreased by one-third for dodecyl 5a-carba-beta-D-galactopyranoside 5b. Observation of similar levels for 5a'-carba-beta-lactoside 7b under both cellular and cell-free conditions suggested that enzymes are likely to recognize the pyranose oxygen atom. (C) 2009 Elsevier Ltd. All rights reserved.