allyl α-D-isopropylidene-α-D-fucopyranoside | 201858-29-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl α-D-isopropylidene-α-D-fucopyranoside
• 英文别名: allyl α-D-fuco-pyranoside；allyl α-D-fucopyranoside；allyl α-D-fucoside；(2S,3R,4S,5R,6R)-2-(Allyloxy)-6-methyltetrahydro-2H-pyran-3,4,5-triol；(2R,3R,4S,5R,6S)-2-methyl-6-prop-2-enoxyoxane-3,4,5-triol
• CAS: 201858-29-9
• 化学式: C₉H₁₆O₅
• 分子量: 204.223
• InChiKey: JPOJNSPEUPRVLQ-NXRLNHOXSA-N

物化性质

• 沸点：
  346.8±42.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  79.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  allyl α-D-isopropylidene-α-D-fucopyranoside 在 吡啶 、 sodium azide 、 二正丁基氧化锡 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 29.0h， 生成 [(2S,3R,4S,5R,6R)-5-azido-6-methyl-4-phenylmethoxy-2-prop-2-enoxyoxan-3-yl] 2,2-dimethylpropanoate
  参考文献：
  名称：

  Concise synthesis of Bacillus anthracis exosporium tetrasaccharide via two-stage activation of allyl glycosyl donor strategy

  摘要：

  A highly efficient glycosylation protocol recently developed in our laboratory has been utilized in the short synthesis of the tetrasaccharide 1, an antigen important to the development of carbohydrate-based diagnostic tools and vaccines against anthrax. The protocol employs allyl glycosides as building blocks and improves the overall synthetic efficiency. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.05.089
• 作为产物：
  描述：

  D-Fucose 、 烯丙醇 在 乙酰氯 作用下， 反应 25.0h， 以92%的产率得到allyl α-D-isopropylidene-α-D-fucopyranoside
  参考文献：
  名称：

  Concise synthesis of Bacillus anthracis exosporium tetrasaccharide via two-stage activation of allyl glycosyl donor strategy

  摘要：

  A highly efficient glycosylation protocol recently developed in our laboratory has been utilized in the short synthesis of the tetrasaccharide 1, an antigen important to the development of carbohydrate-based diagnostic tools and vaccines against anthrax. The protocol employs allyl glycosides as building blocks and improves the overall synthetic efficiency. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.05.089

文献信息

• Synthesis and Structure Verification of the Vaccine Adjuvant QS-7-Api. Synthetic Access to Homogeneous <i>Quillaja saponaria</i> Immunostimulants
  作者：Kai Deng、Michelle M. Adams、David Y. Gin

  DOI：10.1021/ja801008m

  日期：2008.5.1

  is significantly less toxic than QS-21, a related saponin that is currently the favored adjuvant in anticancer and antiviral vaccine clinical trials. Tedious isolation/purification protocols and uncertainty in its structural constitution have hindered the clinical development of QS-7. A chemical synthesis of QS-7-Api is described, providing structural verification of the adjuvant. A novel semisynthetic

  QS-7-Api 是一种非常有效的免疫佐剂，从皂荚树的树皮中分离出来。它的毒性明显低于 QS-21，一种相关的皂苷，目前是抗癌和抗病毒疫苗临床试验中的首选佐剂。繁琐的分离/纯化方案及其结构构成的不确定性阻碍了 QS-7 的临床开发。描述了 QS-7-Api 的化学合成，提供了佐剂的结构验证。还建立了 QS-7-Api 的新型半合成序列，极大地促进了 QS-7 的临床前和临床评估。
• Green glycosylation promoted by reusable biomass carbonaceous solid acid: an easy access to β-stereoselective terpene galactosides
  作者：Bala Kishan Gorityala、Jimei Ma、Kalyan Kumar Pasunooti、Shuting Cai、Xue-Wei Liu

  DOI：10.1039/c0gc00883d

  日期：——

  An efficient green protocol has been developed for the atom economic glycosylation of unprotected, unactivated glycosyl donors and glycosylation of glycosyl trichloroacetimidates with the aid of reusable eco-friendly biomass carbonaceous solid acid as catalyst.

  开发了一种高效的绿色协议，用于无保护、未活化的糖苷供体的原子经济糖苷化，以及在可重复使用的环保生物质碳酸固体酸催化剂的帮助下对糖苷三氯乙酰亚胺的糖苷化。
• Synthesis of (25R)-ruscogenin-1-yl β-d-xylopyranosyl-(1→3)-[β-d-glucopyranosyl-(1→2)]-β-d-fucopyranoside
  作者：Meizheng Liu、Biao Yu*、Xiangyang Wu、Yongzheng Hui*、Kwok-Pui Fung

  DOI：10.1016/s0008-6215(00)00244-5

  日期：2000.12

  The synthesis of (25R)-ruscogenin-1-yl beta -D-xylopyranosyl-(1 --> 3)-[beta -D-glucopyranosyl-(1 --> 2)]-beta -D-fucopyranoside, a saponin from the tuber of Liriope muscari (Decne.) Bailey, is described. (C) 2000 Elsevier Science Ltd. All rights reserved.
• [EN] TRITERPENE SAPONINS, METHODS OF SYNTHESIS, AND USES THEREOF<br/>[FR] SAPONINES TRITERPÉNIQUES, PROCÉDÉS DE SYNTHÈSE ET UTILISATIONS DE CELLES-CI
  申请人：SLOAN KETTERING INST CANCER

  公开号：WO2009126737A3

  公开（公告）日：2010-01-14
• First total synthesis of 25(R)-ruscogenin-1-yl β-D-xylopyranosyl-(1→3)-[β-D-glucopyranosyl-(1→2)]-β-D-fucopyranoside, an ophiopogonis saponin from the tuber of Liriope muscari (Decne.)
  作者：Meizheng Liu、Biao Yu、Yongzheng Hui

  DOI：10.1016/s0040-4039(97)10536-6

  日期：1998.1

  The first total synthesis of 25(R)-ruscogenin-1-yl beta-D-xylopyranosyl-(1-->3)-[beta-D-glucopyranosyl-(1-->)]-beta-D-fucopyranoside (1), an Ophiopogonis saponin with strong anti-inflammatory and immunopharmacological activities from the tuber of Liriope musrari (Decne.), is described. The glycosylaton of a highly hindered alcohol by Schmidt's "inverse procedure" is demonstrated. (C) 1997 Elsevier Science Ltd. All rights reserved.