3-O-allyl-2,4,6-tri-O-benzoyl-D-galactopyranosyl trichoroacetimidate | 493027-41-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-O-allyl-2,4,6-tri-O-benzoyl-D-galactopyranosyl trichoroacetimidate
• 英文别名: Bz(-2)[allyl(-3)][Bz(-4)][Bz(-6)]Gal-O-C(NH)CCl3；[(2R,3S,4S,5R)-3,5-dibenzoyloxy-4-prop-2-enoxy-6-(2,2,2-trichloroethanimidoyl)oxyoxan-2-yl]methyl benzoate
• CAS: 493027-41-1
• 化学式: C₃₂H₂₈Cl₃NO₉
• 分子量: 676.935
• InChiKey: KJZNKLZPQXXGDH-ZERIZBQBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  45
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  130
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3-O-allyl-2,4,6-tri-O-benzoyl-D-galactopyranosyl trichoroacetimidate 在 三氟甲磺酸 、 4 A molecular sieve 、 水 、 溶剂黄146 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 1.5h， 生成
  参考文献：
  名称：

  Chemoenzymatic synthesis of sulfated O-linked oligosaccharides: epitopes for MECA-79

  摘要：

  Sulfated oligosaccharides I,II and III, representatives of those found on L-selectin counterreceptors, have been efficiently prepared employing a combination of chemical and enzymatic synthetic methods. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01795-1
• 作为产物：
  描述：

  对甲氧苯基-3-O-烯丙基-β-D-吡喃半乳糖苷 在 吡啶 、 ammonium cerium(IV) nitrate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 水 、 甲苯 、 乙腈 为溶剂， 生成 3-O-allyl-2,4,6-tri-O-benzoyl-D-galactopyranosyl trichoroacetimidate
  参考文献：
  名称：

  Chemoenzymatic synthesis of sulfated O-linked oligosaccharides: epitopes for MECA-79

  摘要：

  Sulfated oligosaccharides I,II and III, representatives of those found on L-selectin counterreceptors, have been efficiently prepared employing a combination of chemical and enzymatic synthetic methods. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01795-1

文献信息

• A practical synthesis of β-d-GlcA-(1→3)-β-d-Gal-(1→3)-β-d-Gal-(1→4)-d-Xyl, a part of the common linkage region of a glycosaminoglycan
  作者：Langqiu Chen、Fanzuo Kong

  DOI：10.1016/s0008-6215(02)00169-6

  日期：2002.9

  A practical synthesis of beta-D-GlcA-(1 --> 3)-beta-D-Gal-(1 --> 3)-beta-D-Gal-(1 -->4)-beta-D-Xyl-(1 --> OMe) was achieved by coupling of methyl 2,3,4-tri-O-acetyl-alpha-D-glucopyranosyluronate trichloroacetimidate with a trisaccharide acceptor. The trisaccharide acceptor was obtained by condensation of 3-O-allyl-2,4,6-tri-O-benzoyl-beta-D-galactopyranosyl-(1 --> 3)-2,4,6-tri-O-benzoyl-alpha-D-galactopyranosyl trichloroacetimidate with methyl 2,3-di-O-benzoyl-beta-D-xylopyranoside, followed by deallylation. The beta-(1 --> 3)-linked disaccharide was prepared readily with p-methoxyphenyl 3-O-allyl-2,4,6-tri-O-benzoyl-beta-D-galactopyranoside as the key synthon. The alpha-(1--> 3)-linkage was formed in considerable amount with galactose mono- and disaccharide trichloroacetimidate donors with C-2 neighboring group participation. CO 2002 Elsevier Science Ltd. All rights reserved.
• Chemoenzymatic synthesis of sulfated O-linked oligosaccharides: epitopes for MECA-79
  作者：Frederic Bélot、David Rabuka、Minoru Fukuda、Ole Hindsgaul

  DOI：10.1016/s0040-4039(02)01795-1

  日期：2002.10

  Sulfated oligosaccharides I,II and III, representatives of those found on L-selectin counterreceptors, have been efficiently prepared employing a combination of chemical and enzymatic synthetic methods. (C) 2002 Elsevier Science Ltd. All rights reserved.