[(2R,3R,4S,5S,6R)-4,5-diacetyloxy-6-bromo-2-(methylsulfonyloxymethyl)oxan-3-yl] acetate | 68354-94-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2R,3R,4S,5S,6R)-4,5-diacetyloxy-6-bromo-2-(methylsulfonyloxymethyl)oxan-3-yl] acetate
• CAS: 68354-94-9
• 化学式: C₁₃H₁₉BrO₁₀S
• 分子量: 447.258
• InChiKey: UTUXVPYHYRUEHL-BNDIWNMDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  140
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4S,5S,6R)-4,5-diacetyloxy-6-bromo-2-(methylsulfonyloxymethyl)oxan-3-yl] acetate 生成 2-S-(2,3,4-tri-O-acetyl-6-O-methylsulfonyl-α-D-mannopyranosyl)-2-thiopseudourea
  参考文献：
  名称：

  BALDESCHWIELER, J. D.;GAMBLE, R. C.;MAUK, M. R.;SHEN, TSUNG-YING;PONPIPOM+

  摘要：

  DOI：
• 作为产物：
  描述：

  [(2R,3R,4S,5S)-4,5,6-triacetyloxy-2-(methylsulfonyloxymethyl)oxan-3-yl] acetate 生成 [(2R,3R,4S,5S,6R)-4,5-diacetyloxy-6-bromo-2-(methylsulfonyloxymethyl)oxan-3-yl] acetate
  参考文献：
  名称：

  BALDESCHWIELER, J. D.;GAMBLE, R. C.;MAUK, M. R.;SHEN, TSUNG-YING;PONPIPOM+

  摘要：

  DOI：

文献信息

• A facile method for the preparation of sugar orthoesters promoted by anhydrous sodium bicarbonate
  作者：Shanqiao Wei、Jinzhong Zhao、Huawu Shao

  DOI：10.1139/v09-146

  日期：2009.12

  A facile and eco-friendly method for the preparation of sugar orthoesters by using anhydrous sodium bicarbon- ate is described. Various sugar orthoesers, including sugar-sugar orthoesters, were synthesized in good-to-excellent yields by the reaction of a protected glycosyl bromide with an alcohol or sugar.

  描述了一种使用无水碳酸氢钠制备糖原酸酯的简便且环保的方法。通过受保护的糖基溴与醇或糖的反应，以良好到优异的收率合成了各种糖原酸酯，包括糖-糖原酸酯。
• Environmentally Benign Synthesis of Sugar Orthoesters Promoted by Anhydrous Sodium Acetate and Ultrasound
  作者：Jinzhong Zhao、Shanqiao Wei、Aiqin Yue、Huawu Shao

  DOI：10.1002/cjoc.201100385

  日期：2012.3

  A convenient and alternative procedure for the synthesis of sugar orthoesters from glycosyl bromides with anhydrous sodium acetate as base under ultrasound irradiation is described. Various sugar and sugar‐sugar orthoesters were prepared in 70&percnt–91&percnt isolated yields.

  描述了一种在超声辐射下用无水乙酸钠为基础由糖基溴化物合成糖原酸酯的方便且可替代的方法。各种糖和糖原糖的制备产率为70％至91％。
• A simple and convenient method for the synthesis of pyranoid glycals
  作者：Jinzhong Zhao、Shanqiao Wei、Xiaofeng Ma、Huawu Shao

  DOI：10.1016/j.carres.2009.10.003

  日期：2010.1

  A simple, mild, and environmentally benign synthesis procedure of pyranoid glycals is described. In a novel fashion, protected glycopyranosyl bromides undergo the reductive elimination in the presence of zinc in phosphate buffer at room temperature. The pyranoid glycals were obtained in good-to-excellent yields (18 examples).

  描述了一种简单，温和的，对环境有益的吡喃糖类合成方法。以新颖的方式，在室温下在磷酸盐缓冲液中存在锌的情况下，受保护的吡喃葡萄糖基溴化物经历了还原消除。以良好至优异的产率获得了吡喃类糖（18个实施例）。
• Lipid vesicles bearing carbohydrate surfaces as lymphatic directed vehicles for therapeutic and diagnostic substances, their use and method of preparing them
  申请人：Merck & Co., Inc.

  公开号：EP0028917A2

  公开（公告）日：1981-05-20

  Lipid vesicles comprise a lipid bilayer which includes an analog of a cell-surface receptor such as dicetyl phosphate, stearylamine, 6-(5-cholesten-3β-yloxy)hexyl 1-thio-β-L-fucopyranoside, 6-(5-cholesten-3β-yloxy)hexyl 1-thio-β-D-galactopyranoside, 6-(5-cholesten- 3β-yloxy)hexyl 1-thio-a- D-mannopyranoside, 6-(5-cholesten- 3-yloxy)hexyl 2-acetamido-3-deoxy- 1-thio-β-D-galactopyranoside, 6-(5-cholesten- 3β-yloxy)hexyl 6-amino-6-deoxy-1-thio- β-D-galactopyranoside or 6-(5-cholesten- 3p-yloxy)hexyl 6-amino-6-deoxy-1- thio-a-D-mannopyranoside, together with cholesterol, distearoyl phospatidylcholine and an effective amount of a physiologically compatible radioactive tracer or a cytotoxic or therapeutic agent as a part of the vesicles. The vesicles of this invention can be administered to mammalian, including human, hosts and have been found to release the contents of the vesicles in a predetermined manner, and in some cases to be rapidly concentrated in the lymphatic system and/or liver, lungs, or spleen of the host.

  脂质囊泡由脂质双分子层组成，其中包括细胞表面受体的类似物，如磷酸二十六烷基酯、硬脂胺、6-(5-胆甾烯-3β-氧基)己基 1-硫代-β-L-吡喃葡萄糖苷、6-(5-胆甾烯-3β-氧基)己基 1-硫代-β-D-吡喃半乳糖苷、6-(5-胆甾烯-3β-氧基)己基 1-硫代-β-D-吡喃半乳糖苷、6-(5-胆甾烯-3β-氧基)己基 1-硫代-a-D-吡喃甘露糖苷、6-(5-胆甾烯-3-氧基)己基 2-乙酰氨基-3-脱氧-1-硫代-β-D-吡喃半乳糖苷、6-(5-胆甾烯-3β-氧基)己基 6-氨基-6-脱氧-1-硫代-β-D-吡喃半乳糖苷或 6-(5-胆甾烯-3p-氧基)己基 6-氨基-6-脱氧-1-硫代-a-D-吡喃甘露糖苷，以及胆固醇、二硬脂酰磷脂酰胆碱和有效量的生理相容放射性示踪剂或细胞毒性或治疗剂，作为囊泡的一部分。本发明的囊泡可以给哺乳动物（包括人类）宿主服用，并且发现囊泡中的内容物会以预定的方式释放出来，在某些情况下会迅速集中在宿主的淋巴系统和/或肝、肺或脾中。
• New glycolipid compound useful as immunologic adjuvant and its preparation
  申请人：Merck & Co., Inc.

  公开号：EP0007277B1

  公开（公告）日：1983-02-09