O¹,O²-isopropylidene-O³-methyl-O⁵-trityl-α-D-xylofuranose | 67850-91-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: O¹,O²-isopropylidene-O³-methyl-O⁵-trityl-α-D-xylofuranose
• 英文别名: O¹,O²-Isopropyliden-O³-methyl-O⁵-trityl-α-D-xylofuranose；1,2-O-isopropylidene-3-methoxy-5-O-trityl-D-xylofuranose；(3aR,5R,6S,6aR)-6-methoxy-2,2-dimethyl-5-(trityloxymethyl)-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole
• CAS: 67850-91-3
• 化学式: C₂₈H₃₀O₅
• 分子量: 446.543
• InChiKey: LKRQDVLHFNKFAB-XDZVQPMWSA-N

物化性质

• 沸点：
  533.7±50.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  O¹,O²-isopropylidene-O³-methyl-O⁵-trityl-α-D-xylofuranose 在 indium(III) chloride 、 水 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以92%的产率得到((3aR,5R,6S,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-methanol
  参考文献：
  名称：

  Yadav; Reddy, B.V. Subba; Srinivas, Journal of Chemical Research - Part S, 2001, # 12, p. 528 - 529

  摘要：

  DOI：
• 作为产物：
  描述：

  1,2-O-异亚丙基-alpha-D-呋喃木糖 在 吡啶 、 silver(l) oxide 作用下， 生成 O¹,O²-isopropylidene-O³-methyl-O⁵-trityl-α-D-xylofuranose
  参考文献：
  名称：

  Levene; Raymond, Journal of Biological Chemistry, 1933, vol. 102, p. 317,323

  摘要：

  DOI：

文献信息

• Saponin and sapogenol. XXVI. Steroidal saponins from the starfish Acanthaster planci L. (crown of thorns). 2. Structure of the major saponin thornasteroside A.
  作者：ISAO KITAGAWA、MOTOMASA KOBAYASHI

  DOI：10.1248/cpb.26.1864

  日期：——

  The major saponin named thornasteroside A (5) has been isolated from the whole body of starfish Acanthaster planci L. (crown of thorns). In order to facilitate the structural study, thornasteroside A (5) has been converted to a pentaglycoside (designated as dsp-1), which corresponds to a desulfated pregnane-type derivative of 5. On the bases of chemical reactions and physicochemical evidence, the structure of dsp-1 has been elucidated as 10. Based on the accumulated evidence in this and the preceding papers, the structure of thornasteroside A has been established as 20-hydroxy-6α-O-β-D-fucopyranosyl (1→2)-β-D-galactopyranosyl (1→4)-[β-D-quinovopyranosyl (1→2)]-β-D-xylopyranosyl (1→3)-β-D-quinovopyranosyl}-5α-cholest-9 (11)-en-23-on-3β-yl sodium sulfate (5).

  从棘冠海星（Acanthaster planci L.）全身分离得到主要皂苷成分thornasteroside A（5）。为了便于结构研究，将thornasteroside A（5）转化为一种五糖苷（命名为dsp-1），相当于去硫酸化的孕甾烷衍生物。根据化学反应和物化证据，dsp-1的结构被阐明为10。基于本篇及前述论文积累的证据，thornasteroside A的结构被确定为20-羟基-6α-O-β-D-岩藻吡喃糖基（1→2）-β-D-半乳吡喃糖基（1→4）-[β-D-苦苣吡喃糖基（1→2）]-β-D-木吡喃糖基（1→3）-β-D-苦苣吡喃糖基}-5α-胆甾-9（11）-烯-23-酮-3β-基硫酸钠（5）。
• Tris(pentafluorophenyl)borane: a mild and efficient catalyst for the chemoselective tritylation of alcohols
  作者：Ch. Raji Reddy、G. Rajesh、S.V. Balaji、N. Chethan

  DOI：10.1016/j.tetlet.2007.12.020

  日期：2008.2

  described using triphenylmethanol in the presence of tris(pentafluorophenyl)borane (3 mol %) in dichloromethane at room temperature. The chemoselectivity of this protocol is demonstrated by studying the tritylation of a primary alcohol in the presence of a secondary alcohol and also the mildness of this catalyst was studied with substrates containing acid labile protecting groups.

  描述了在室温下在二氯甲烷中在三（五氟苯基）硼烷（3mol％）存在下使用三苯甲醇，有效地酸催化的醇作为三苯甲基醚的保护。通过研究在仲醇存在下伯醇的三苯甲基化来证明该方案的化学选择性，并且还使用含有酸不稳定保护基的底物研究了该催化剂的温和性。
• 3,5-DISUBSTITUTED AND 3,5,7-TRISUBSTITUTED-3H-OXAZOLO AND 3H-THIAZOLO[4,5-d]PYRIMIDIN-2-ONE COMPOUNDS AND PRODRUGS THEREOF
  申请人：Webber Stephen E.

  公开号：US20110275589A1

  公开（公告）日：2011-11-10

  The invention is directed to 3,5-disubstituted and 3,5,7-trisubstituted-3H-oxazolo and 3H-thiazolo[4,5-d]pyrimidin-2-one compounds and prodrugs thereof that have immunomodulatory activity. The invention is also directed to the therapeutic or prophylactic use of such compounds and pharmaceutical compositions containing them, and to methods of treating diseases and disorders described herein, by administering effective amounts of such compounds and prodrugs.

  本发明涉及具有免疫调节活性的3,5-二取代和3,5,7-三取代-3H-噁唑并[4,5-d]嘧啶-2-酮化合物及其前药。本发明还涉及使用此类化合物及其前药的治疗或预防用途，以及含有它们的制药组合物和通过给予这些化合物和前药的有效量来治疗本文所述疾病和疾病的方法。
• 3,5-DISUBSTITUTED AND 3,5,7-TRISUBSTITUTED-3H-OXAZOLO AND 3H-THIAZOLO[4,5-D]PYRIMIDIN-2-ONE COMPOUNDS AND PRODRUGS THEREOF
  申请人：Webber Stephen E.

  公开号：US20120121541A1

  公开（公告）日：2012-05-17

  The invention is directed to 3,5-disubstituted and 3,5,7-trisubstituted-3H-oxazolo and 3H-thiazolo[4,5-d]pyrimidin-2-one compounds and prodrugs thereof that have immunomodulatory activity. The invention is also directed to the therapeutic or prophylactic use of such compounds and pharmaceutical compositions containing them, and to methods of treating diseases and disorders described herein, by administering effective amounts of such compounds and prodrugs.

  本发明涉及具有免疫调节活性的3,5-二取代和3,5,7-三取代-3H-噁唑和3H-噻唑[4,5-d]嘧啶-2-酮化合物及其前药。本发明还涉及使用这些化合物和前药的治疗或预防用途，以及含有它们的制药组合物，并通过给予这些化合物和前药的有效剂量来治疗本文所述的疾病和障碍的方法。
• 3,5-Disubstituted and 3,5,7-Trisubstituted-3H-Oxazolo and 3H-Thiazolo[4,5-d]pyrimidin-2-one Compounds and Prodrugs Thereof
  申请人：Webber Stephen E.

  公开号：US20130259831A1

  公开（公告）日：2013-10-03

  The invention is directed to 3,5-disubstituted and 3,5,7-trisubstituted-3H-oxazolo and 3H-thiazolo[4,5-d]pyrimidin-2-one compounds and prodrugs thereof that have immunomodulatory activity. The invention is also directed to the therapeutic or prophylactic use of such compounds and pharmaceutical compositions containing them, and to methods of treating diseases and disorders described herein, by administering effective amounts of such compounds and prodrugs.

  该发明涉及具有免疫调节活性的3,5-二取代和3,5,7-三取代-3H-噁唑并[4,5-d]嘧啶-2-酮化合物及其前药。该发明还涉及使用这些化合物的治疗或预防用途，以及含有它们的制药组合物，以及通过给予这些化合物和前药的有效量来治疗本文所述的疾病和障碍的方法。