2,3,4-tri-O-benzoyl-β-D-xylopyranosyl-(1->3)-2,4-di-O-benzoyl-D-xylopyranosyl trichloroacetimidate | 502765-09-5

• 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-benzoyl-β-D-xylopyranosyl-(1->3)-2,4-di-O-benzoyl-D-xylopyranosyl trichloroacetimidate
• 英文别名: Bz(-2)[Bz(-3)][Bz(-4)]Xyl(b1-3)[Bz(-2)][Bz(-4)]Xyl-O-C(NH)CCl3；[(3R,4S,5R,6S)-4,5-dibenzoyloxy-6-[(3R,4S,5R)-3,5-dibenzoyloxy-2-(2,2,2-trichloroethanimidoyl)oxyoxan-4-yl]oxyoxan-3-yl] benzoate
• CAS: 502765-09-5
• 化学式: C₄₇H₃₈Cl₃NO₁₄
• 分子量: 947.176
• InChiKey: NSMQFACQLLKHAE-XCHUFOIWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.6
• 重原子数：
  65
• 可旋转键数：
  19
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  192
• 氢给体数：
  1
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  allyl 2-O-acetyl-3-O-benzyl-α-L-rhamnopyranoside 、 2,3,4-tri-O-benzoyl-β-D-xylopyranosyl-(1->3)-2,4-di-O-benzoyl-D-xylopyranosyl trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 、 4 Angstroem MS 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以77%的产率得到allyl 2,3,4-tri-O-benzoyl-β-D-xylopyranosyl-(1->3)-2,4-di-O-benzoyl-β-D-xylopyranosyl-(1->4)-2-O-acetyl-3-O-benzyl-α-L-rhamnopyranoside
  参考文献：
  名称：

  Silver(I) oxide-mediated regioselective 2-monoacylation in 3-O-benzyl-α-l-rhamnopyranosides and application in synthesis of a protected tetrasaccharide fragment of potent cytotoxic saponins gleditsiosides C and D

  摘要：

  The axial 2-hydroxyl group of methyl and allyl 3-O-benzyl-alpha-L-rhamnopyranosides was selectively acylated in 56-78% yields by reaction with 1. 1 equiv of acyl chloride in the presence of 1. 5 equiv of silver(I) oxide. Use of the method permitted a convenient synthesis of a protected tetrasaccharide fragment of triterpene saponins gleditsiosides C and D. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.03.001
• 作为产物：
  描述：

  benzyl 2,3,4-tri-O-benzoyl-β-D-xylopyranosyl-(1->3)-2,4-di-O-benzoyl-α-D-xylopyranoside 、 三氯乙腈 在 palladium on activated charcoal 乙醇 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 25.0h， 以71%的产率得到2,3,4-tri-O-benzoyl-β-D-xylopyranosyl-(1->3)-2,4-di-O-benzoyl-D-xylopyranosyl trichloroacetimidate
  参考文献：
  名称：

  Silver(I) oxide-mediated regioselective 2-monoacylation in 3-O-benzyl-α-l-rhamnopyranosides and application in synthesis of a protected tetrasaccharide fragment of potent cytotoxic saponins gleditsiosides C and D

  摘要：

  The axial 2-hydroxyl group of methyl and allyl 3-O-benzyl-alpha-L-rhamnopyranosides was selectively acylated in 56-78% yields by reaction with 1. 1 equiv of acyl chloride in the presence of 1. 5 equiv of silver(I) oxide. Use of the method permitted a convenient synthesis of a protected tetrasaccharide fragment of triterpene saponins gleditsiosides C and D. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.03.001

文献信息

• An efficient and practical synthesis of β-(1→3)-linked xylooligosaccharides
  作者：Langqiu Chen、Fanzuo Kong

  DOI：10.1016/s0008-6215(02)00285-9

  日期：2002.11

  A facile and practical method was developed for the synthesis of β-(1→3)-linked xylooligosaccharides. Dibezoylation of allyl α-d-xylopyranoside (1) afforded 2,4-dibenzoate 6 as the major product. Chloroacetylation of 6, followed by deallylation and trichloroacetimidation, gave a 1:3 α/β imidate (10 and 11) mixture. Coupling of the imidate mixture with 6 gave a disaccharide 13, whose dechloroacetylation

  开发了一种简便实用的方法来合成β-（1→3）-连接的木寡糖。烯丙基α-d-吡喃吡喃糖苷（1）的二苯甲酰化得到2,4-二苯甲酸酯6作为主要产物。6的氯乙酰化，然后脱铝和三氯乙酰亚胺化，得到1：3的α/β亚氨酸酯（10和11）混合物。亚氨酸酯混合物与6偶联得到二糖13，其脱氯乙酰基化得到二糖受体16。过苯甲酰化木糖基α/β亚氨酸酯（7和8）混合物与6缩合得到二糖12。二糖供体为1：1α/β混合物。二糖供体混合物与二糖受体16的偶联产生四糖17。重复脱铝和三氯乙酰亚胺化将17转化为四糖供体混合物。四糖供体混合物与受体16的缩合得到六糖21。用饱和氨水-甲醇进行脱苯甲酰化，得到β-（1→3）连接的烯丙基木糖四糖苷和木糖六糖苷。
• Silver(I) oxide-mediated regioselective 2-monoacylation in 3-O-benzyl-α-l-rhamnopyranosides and application in synthesis of a protected tetrasaccharide fragment of potent cytotoxic saponins gleditsiosides C and D
  作者：Qian Yang、Ming Lei、Qin-Jian Yin、Jin-Song Yang

  DOI：10.1016/j.carres.2007.03.001

  日期：2007.7

  The axial 2-hydroxyl group of methyl and allyl 3-O-benzyl-alpha-L-rhamnopyranosides was selectively acylated in 56-78% yields by reaction with 1. 1 equiv of acyl chloride in the presence of 1. 5 equiv of silver(I) oxide. Use of the method permitted a convenient synthesis of a protected tetrasaccharide fragment of triterpene saponins gleditsiosides C and D. (C) 2007 Elsevier Ltd. All rights reserved.