2,3,4-tri-O-levulinoyl-β-D-xylopyranosyl chloride | 343254-32-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2,3,4-tri-O-levulinoyl-β-D-xylopyranosyl chloride
• 英文别名: 1-chloro-2,3,4-tri-O-levulinoyl-α-D-xylopyranose；[(3R,4S,5R,6R)-6-chloro-4,5-bis(4-oxopentanoyloxy)oxan-3-yl] 4-oxopentanoate
• CAS: 343254-32-0
• 化学式: C₂₀H₂₇ClO₁₀
• 分子量: 462.881
• InChiKey: BWPBIBMNDIOZSG-YGBSJELFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  31
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  139
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-levulinoyl-β-D-xylopyranosyl chloride 在 (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate 四氮唑 、 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 4 Angstroem MS 、 MS AW₃₀₀ 、 氢气 、 silver trifluoromethanesulfonate 、 乙酸肼 、 二正丁基氧化锡 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 吡啶 、 乙醚 、 乙醇 、 二氯甲烷 、 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 13.58h， 生成 N-benzyloxycarbonyl-O-[O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->3)-O-(2-O-acetyl-4,6-O-benzylidene-β-D-galactopyranosyl)-(1->4)-(3-O-acetyl-2-O-dibenzyloxyphosphinyl-β-D-xylopyranosyl)]-L-serine benzyl ester
  参考文献：
  名称：

  Synthesis of Phosphorylated and Sulfated Glycosyl Serines in the Linkage Region of the Glycosaminoglycans

  摘要：

  We synthesized novel acidic glycans having acidic groups located in the linkage region of the glycosaminoglcans (GAGs). The targeted compounds, beta -D-Xyl(2P)-Ser (1), beta -D-Gal(+/- 6S)-(1 -->4)-beta- D-Xyl(2P)-Ser (3 and 2), beta -D-Gal(+/- 6S)-(1 -->3)-beta -D-Gal-(1 -->4)-beta -D-Xyl(2P)-Ser (5 and 4), and beta -D-Gal- (1 -->3)-beta -D-Gal(6S)-(1 -->4)-beta -D-Xyl(2P)-Ser (6) contain phosphate and/or sulfate at the specified positions. Some of them (3,5, and 6) are the first synthesized examples of natural-type glycoconjugates that simultaneously possess phosphate and sulfate as well as carboxylic acid.

  DOI：

  10.1021/jo001540h
• 作为产物：
  描述：

  D-吡喃木糖 在 吡啶 、 4-二甲氨基吡啶 、 四氯化钛 作用下， 以 1,2-二氯乙烷 为溶剂， 生成 2,3,4-tri-O-levulinoyl-β-D-xylopyranosyl chloride
  参考文献：
  名称：

  Synthesis of Phosphorylated and Sulfated Glycosyl Serines in the Linkage Region of the Glycosaminoglycans

  摘要：

  We synthesized novel acidic glycans having acidic groups located in the linkage region of the glycosaminoglcans (GAGs). The targeted compounds, beta -D-Xyl(2P)-Ser (1), beta -D-Gal(+/- 6S)-(1 -->4)-beta- D-Xyl(2P)-Ser (3 and 2), beta -D-Gal(+/- 6S)-(1 -->3)-beta -D-Gal-(1 -->4)-beta -D-Xyl(2P)-Ser (5 and 4), and beta -D-Gal- (1 -->3)-beta -D-Gal(6S)-(1 -->4)-beta -D-Xyl(2P)-Ser (6) contain phosphate and/or sulfate at the specified positions. Some of them (3,5, and 6) are the first synthesized examples of natural-type glycoconjugates that simultaneously possess phosphate and sulfate as well as carboxylic acid.

  DOI：

  10.1021/jo001540h

文献信息

• Regio- and stereo-controlled synthesis of β-Xyl(1–4)Rbo-5P1-Rbo, the partial structure of O-mannosyl glycan
  作者：Takahiro Tamura、Jun-ichi Tamura

  DOI：10.1016/j.tetlet.2018.12.065

  日期：2019.2

  intracellular cytoskeleton and extracellular matrix, such as laminin in skeletal muscle. We synthesized β-d-Xyl-(1–4)-d-Rbo-5P (1), β-d-Xyl-(1–4)-d-Rbo (2), and β-d-Xyl-(1–4)-d-Rbo-5P1-d-Rbo (3), partial structures of O-mannosyl glycan, in regio- and stereo-controlled manners, and demonstrated compatibility with the natural product.

  O-甘露糖基聚糖是α-dystroglycan的关键聚糖部分，它充当跨膜连接体，连接细胞内细胞骨架和细胞外基质，例如骨骼肌中的层粘连蛋白。我们合成了β- d -Xyl-（1-4）-d -Rbo-5P（1），β- d -Xyl-（1-4）-d -Rbo（2）和β- d -Xyl-（（ 1–4）-d -Rbo-5P1- d -Rbo（3），O-甘露糖基聚糖的部分结构，以区域和立体方式控制，并证明了与天然产物的相容性。