1,2,3,6-tetra-O-acetyl-4-O-[2,4-di-O-acetal-6'-O-(t-butyldimethylsilyl)-β-D-galactopyranosyl]-α-D-mannopyranose | 688317-20-6

• 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: 1,2,3,6-tetra-O-acetyl-4-O-[2,4-di-O-acetal-6'-O-(t-butyldimethylsilyl)-β-D-galactopyranosyl]-α-D-mannopyranose
• 英文别名: TBDMS(-6)Gal2Ac4Ac(b1-4)a-Man1Ac2Ac3Ac6Ac；[(2R,3R,4S,5S,6R)-4,5,6-triacetyloxy-3-[(2S,3R,4S,5R,6R)-3,5-diacetyloxy-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-hydroxyoxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 688317-20-6
• 化学式: C₃₀H₄₈O₁₇Si
• 分子量: 708.786
• InChiKey: UQKYEJQNBREZGS-AMCNKCEQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.06
• 重原子数：
  48
• 可旋转键数：
  19
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  215
• 氢给体数：
  1
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  1,2,3,6-tetra-O-acetyl-4-O-[2,4-di-O-acetal-6'-O-(t-butyldimethylsilyl)-β-D-galactopyranosyl]-α-D-mannopyranose 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 氢氟酸 作用下， 以 乙醚 、 乙腈 为溶剂， 反应 6.0h， 生成 1,2,3,6-tetra-O-acetyl-4-O-[3'-O-{2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl}-2,4-di-O-acetyl-β-D-galactopyranosyl]-α-D-mannopyranose
  参考文献：
  名称：

  A facile and novel route to the antigenic branched phosphoglycan of the protozoan Leishmania major parasite

  摘要：

  A novel approach for the iterative synthesis of the antigenic branched phosphoglycan of the protozoan parasite Leishmania major is presented that exploits remarkable dual selectivity in the functionalization of D-lactal, providing flexibility to extend the PG chain either towards the reducing or nonreducing end. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.01.155
• 作为产物：
  描述：

  1,2,3,6-tetra-O-acetyl-4-O-[2,4-di-O-acetyl-3'-O-(p-methoxybenzyl)-6'-O-(tert-butyldimethylsilyl)-β-D-galactopyranosyl]-α-D-mannopyranose 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 12.0h， 以85%的产率得到1,2,3,6-tetra-O-acetyl-4-O-[2,4-di-O-acetal-6'-O-(t-butyldimethylsilyl)-β-D-galactopyranosyl]-α-D-mannopyranose
  参考文献：
  名称：

  A facile and novel route to the antigenic branched phosphoglycan of the protozoan Leishmania major parasite

  摘要：

  A novel approach for the iterative synthesis of the antigenic branched phosphoglycan of the protozoan parasite Leishmania major is presented that exploits remarkable dual selectivity in the functionalization of D-lactal, providing flexibility to extend the PG chain either towards the reducing or nonreducing end. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.01.155