{(2R,3S,4S,5R,6R)-6-Allyloxy-3,5-bis-benzyloxy-4-[(2R,3R,4S,5S,6R)-3,5-bis-benzyloxy-6-hydroxymethyl-4-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yloxy]-tetrahydro-pyran-2-yl}-methanol | 389119-65-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: {(2R,3S,4S,5R,6R)-6-Allyloxy-3,5-bis-benzyloxy-4-[(2R,3R,4S,5S,6R)-3,5-bis-benzyloxy-6-hydroxymethyl-4-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yloxy]-tetrahydro-pyran-2-yl}-methanol
• CAS: 389119-65-7
• 化学式: C₅₁H₅₈O₁₂
• 分子量: 863.014
• InChiKey: YTAJXMDWJLSMAQ-NPRBWLGGSA-N

反应信息

• 作为反应物：
  描述：

  {(2R,3S,4S,5R,6R)-6-Allyloxy-3,5-bis-benzyloxy-4-[(2R,3R,4S,5S,6R)-3,5-bis-benzyloxy-6-hydroxymethyl-4-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yloxy]-tetrahydro-pyran-2-yl}-methanol 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78%的产率得到2-propenyl 2,4-di-O-benzyl-3-O-(2,4-di-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：

  2-propenyl 2-O-benzyl-4,6-benzylidene-3-O-[2-O-benzyl-4,6-O-benzylidene-3-O-(4-methoxybenzyl)-α-D-galactopyranosyl]-β-D-galactopyranoside 在 lithium aluminium tetrahydride 、 三氯化铝 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 30.17h， 以33%的产率得到{(2R,3S,4S,5R,6R)-6-Allyloxy-3,5-bis-benzyloxy-4-[(2R,3R,4S,5S,6R)-3,5-bis-benzyloxy-6-hydroxymethyl-4-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yloxy]-tetrahydro-pyran-2-yl}-methanol
  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