(2R,3R,4S,5R,6R)-2-Allyloxy-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-4-ol | 125790-91-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4S,5R,6R)-2-Allyloxy-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-4-ol
• 英文别名: (2R,3R,4S,5R,6R)-3,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-6-prop-2-enoxyoxan-4-ol
• CAS: 125790-91-2
• 化学式: C₃₀H₃₄O₆
• 分子量: 490.596
• InChiKey: DHWCCCBUFOEVTO-HBMYTODVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  36
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S,5R,6R)-2-Allyloxy-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-4-ol 在 吡啶 、 RhCl(PPh₃)3 、 4 Angstroem MS 、 三氟化硼乙醚 、 sodium hydride 作用下， 以 乙醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 40.0h， 生成 Acetic acid (2R,3S,4S,5R,6R)-4-((2R,3R,4S,5S,6R)-4-acetoxy-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-6-allyloxy-3,5-bis-benzyloxy-tetrahydro-pyran-2-ylmethyl ester
  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 3-O-(4-methoxybenzyl)-β-D-galactopyranoside 在 sodium hydride 、 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， 生成 (2R,3R,4S,5R,6R)-2-Allyloxy-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-4-ol
  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

文献信息

• Linear Synthesis of the Tumor-Associated Carbohydrate Antigens Globo-H, SSEA-3, and Gb3
  作者：Folkert Bosse、Lisa A. Marcaurelle、Peter H. Seeberger

  DOI：10.1021/jo025834+

  日期：2002.9.1

  The tumor-associated carbohydrate antigens Globo-H, SSEA-3, and Gb3 were synthesized in a linear fashion using glycosyl phosphate monosaccharide building blocks. All of the building blocks were prepared from readily available common precursors. The difficult alpha-(1-->4-cis)-galactosidic linkage was installed using a galactosyl phosphate donor with high selectivity. Introduction of the beta-galactosamine unit required the screening a variety of amine protecting groups to ensure good donor reactivity and protecting group compatibility. An N-trichloroacetyl-protected galactosamine donor performed best for the installation of the beta-glycosidic linkage. Conversion of the trichloroacetyl group to the N-acetyl group was achieved under mild conditions, fully compatible with the presence of multiple glycosidic bonds. This synthetic strategy is expected to be amenable to the synthesis of the globo-series of tumor antigens on solid-support.
• Sialylation with systematically protected allyl galactoside acceptors using sialyl phosphate donors
  作者：Kenta Kurimoto、Hatsuo Yamamura、Atsushi Miyagawa

  DOI：10.1016/j.tetlet.2016.02.052

  日期：2016.3

  Various N-protected sialyl donors were synthesized and utilized in sialylation to investigate the reactivity and stereoselectivity of sialyl phosphate donors. Furthermore, in order to understand the effects of protecting groups and hydroxyl group positions on galactosyl acceptors, the sialylation efficiencies of all of the hydroxy groups on galactoses, which were protected with benzyl or benzoyl groups, were investigated. Consequently, the sialylation of N-acetyl-5-N,4-O-oxazolidinone-protected sialyl phosphate donors with allyl galactosides was accomplished and gave the GM4 regioisomers. (C) 2016 Elsevier Ltd. All rights reserved.
• US5576305A
  申请人：——

  公开号：US5576305A

  公开（公告）日：1996-11-19
• US5753631A
  申请人：——

  公开号：US5753631A

  公开（公告）日：1998-05-19