2-propenyl 6-O-acetyl-2,4-di-O-benzyl-β-D-galactopyranoside | 389119-59-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-propenyl 6-O-acetyl-2,4-di-O-benzyl-β-D-galactopyranoside
• 英文别名: [(2R,3R,4S,5R,6R)-4-hydroxy-3,5-bis(phenylmethoxy)-6-prop-2-enoxyoxan-2-yl]methyl acetate
• CAS: 389119-59-9
• 化学式: C₂₅H₃₀O₇
• 分子量: 442.509
• InChiKey: NUHVCVANNLHCFB-ZLOLNMDISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  32
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-propenyl 6-O-acetyl-2,4-di-O-benzyl-β-D-galactopyranoside 在 4 Angstroem MS 、 三氟化硼乙醚 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 2-propenyl 2,4-O-benzyl-3-O-(2,4,6-tri-O-benzyl-α-D-galactopyranosyl)-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of a set of di- and tri-sulfated galabioses

  摘要：

  Among cell-adhesion molecules, L-selectin recognizes sulfated sLe(x) with relatively low affinity. Here, we aimed at artificial mimics by synthesizing a set of di- and tri-sulfated galabioses, which may surpass the affinity of sulfated sLe(x). As a strategy to obtain 3',6',6-tri-O-sulfogalabioses, regioselective reductive cleavage of 4,6- and 4',6'-di-O-benzylidenegalabioses was employed. Two suitably protected galactose precursors were conjugated to yield alpha and beta anomers (48 and 18%, respectively) by using a pentenyl galactoside donor and iodinium di-sym-collidine perchlorate as the catalyst. For synthesizing the 3',6-di-O-sulfogalabiose, however, a trichloroacetimidate donor was superior (52%) to the pentenyl one (30%). (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00222-1
• 作为产物：
  描述：

  Acetic acid (2R,3S,4S,5R,6R)-2-acetoxymethyl-6-allyloxy-3,5-bis-benzyloxy-tetrahydro-pyran-4-yl ester 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 1.0h， 以0.283 g的产率得到2-propenyl 6-O-acetyl-2,4-di-O-benzyl-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of a set of di- and tri-sulfated galabioses

  摘要：

  Among cell-adhesion molecules, L-selectin recognizes sulfated sLe(x) with relatively low affinity. Here, we aimed at artificial mimics by synthesizing a set of di- and tri-sulfated galabioses, which may surpass the affinity of sulfated sLe(x). As a strategy to obtain 3',6',6-tri-O-sulfogalabioses, regioselective reductive cleavage of 4,6- and 4',6'-di-O-benzylidenegalabioses was employed. Two suitably protected galactose precursors were conjugated to yield alpha and beta anomers (48 and 18%, respectively) by using a pentenyl galactoside donor and iodinium di-sym-collidine perchlorate as the catalyst. For synthesizing the 3',6-di-O-sulfogalabiose, however, a trichloroacetimidate donor was superior (52%) to the pentenyl one (30%). (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00222-1