allyl 2,3-O-isopropylidene-α-L-rhamnopyranosyl-(1→2)-3,4-O-isopropylidene-α-D-fucopyranoside | 1455474-96-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 2,3-O-isopropylidene-α-L-rhamnopyranosyl-(1→2)-3,4-O-isopropylidene-α-D-fucopyranoside
• 英文别名: (3aR,4S,6S,7S,7aR)-4-[[(3aS,4R,6S,7R,7aS)-2,2,4-trimethyl-6-prop-2-enoxy-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-yl]oxy]-2,2,6-trimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-ol
• CAS: 1455474-96-0
• 化学式: C₂₁H₃₄O₉
• 分子量: 430.496
• InChiKey: SVWXHTFTGKAIGZ-BCRXHCOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  94.1
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  allyl 2,3-O-isopropylidene-α-L-rhamnopyranosyl-(1→2)-3,4-O-isopropylidene-α-D-fucopyranoside 在 (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate 、 氢气 、 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 24.83h， 生成 2,3,5-tri-O-acetyl-β-D-apiofuranosyl-(1→3)-2,4-di-O-acetyl-β-D-xylopyranosyl-(1→4)-2,3-O-diacetyl-α-L-rhamnopyranosyl-(1→2)-3,4-di-O-acetyl-α-D-fucopyranosyl trichloroacetimidate
  参考文献：
  名称：

  Synthesis of QS-21-Based Immunoadjuvants

  摘要：

  Three structurally defined QS-21-based immune adjuvant candidates (2a-2c) have been synthesized. Application of the two-stage activation glycosylation approach utilizing allyl glycoside building blocks improved the synthetic accessibility of the new adjuvants. The efficient synthesis and establishment of the stand-alone adjuvanticity of the examined synthetic adjuvant (2b) open the door to the pursuit of a new series of structurally defined QS-saponin-based synthetic adjuvants.

  DOI：

  10.1021/jo402118j
• 作为产物：
  描述：

  allyl 2,3-O-isopropylidene-α-L-rhamnopyranoside 在 4-二甲氨基吡啶 、 (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.08h， 生成 allyl 2,3-O-isopropylidene-α-L-rhamnopyranosyl-(1→2)-3,4-O-isopropylidene-α-D-fucopyranoside
  参考文献：
  名称：

  Synthesis of QS-21-Based Immunoadjuvants

  摘要：

  Three structurally defined QS-21-based immune adjuvant candidates (2a-2c) have been synthesized. Application of the two-stage activation glycosylation approach utilizing allyl glycoside building blocks improved the synthetic accessibility of the new adjuvants. The efficient synthesis and establishment of the stand-alone adjuvanticity of the examined synthetic adjuvant (2b) open the door to the pursuit of a new series of structurally defined QS-saponin-based synthetic adjuvants.

  DOI：

  10.1021/jo402118j

文献信息

• [EN] NATURAL SAPONIN-BASED SYNTHETIC IMMUNOADJUVANTS<br/>[FR] IMMUNO-ADJUVANTS SYNTHÉTIQUES À BASE DE SAPONINE NATURELLE
  申请人：UAB RESEARCH FOUNDATION

  公开号：WO2013142142A1

  公开（公告）日：2013-09-26

  The present disclosure encompasses QS-21-based structurally-defined adjuvants to address the need for stronger, safer, and easier-to-access adjuvants. The new compositions can provide tools for addressing long-standing mechanistic questions concerning saponin immune-potentiation through structure-activity-relationship (SAR) studies. Most advantageously, the compounds of the disclosure may be formulated into pharmaceutically acceptable compositions, including vaccines that may be delivered to a subject human or animal subject. The compounds can then act as, for example, an adjuvant to augment an immunological response to a vaccine immunogen.

  本公开涵盖基于QS-21的结构定义佐剂，以解决更强、更安全、更易获得的佐剂需求。新的组合物可以提供工具来通过结构活性关系（SAR）研究解决长期存在的皂苷免疫激活机制问题。最有优势的是，本公开的化合物可以制成药学上可接受的组合物，包括可以提供给人或动物的疫苗。然后，这些化合物可以作为佐剂，例如增强对疫苗免疫原的免疫反应。
• Synthesis of QS-21-Based Immunoadjuvants
  作者：Pengfei Wang、Qipu Dai、Punith Thogaripally、Ping Zhang、Suzanne M. Michalek

  DOI：10.1021/jo402118j

  日期：2013.11.15

  Three structurally defined QS-21-based immune adjuvant candidates (2a-2c) have been synthesized. Application of the two-stage activation glycosylation approach utilizing allyl glycoside building blocks improved the synthetic accessibility of the new adjuvants. The efficient synthesis and establishment of the stand-alone adjuvanticity of the examined synthetic adjuvant (2b) open the door to the pursuit of a new series of structurally defined QS-saponin-based synthetic adjuvants.