6-O-(tert-butyldimethylsilyl)-2,3:4,5-di-O-isopropylidene-D-galactitol | 944560-29-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-O-(tert-butyldimethylsilyl)-2,3:4,5-di-O-isopropylidene-D-galactitol
• 英文别名: [(4S,5R)-5-[(4S,5R)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]methanol
• CAS: 944560-29-6
• 化学式: C₁₈H₃₆O₆Si
• 分子量: 376.566
• InChiKey: KTHPXVWDCIUUDV-YJNKXOJESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.04
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  6-O-(tert-butyldimethylsilyl)-2,3:4,5-di-O-isopropylidene-D-galactitol 、 对甲苯磺酰氯 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 以97%的产率得到6-O-tert-butyldimethylsilyl-2,3:4,5-di-O-isopropylidene-1-O-p-toluenesulfonyl-D-galactitol
  参考文献：
  名称：

  基于FRET的人类岩藻糖基转移酶活性的直接和连续监测：从丰富的D-半乳糖高效合成通用的GDP-L-岩藻糖衍生物。

  摘要：

  我们已经开发了一种简便且通用的协议，用于通过使用荧光能量共振转移（FRET）连续监测人岩藻糖基转移酶的活性，并探索了其在抑制剂筛选测定中的可行性。具有荧光探针的便捷糖核苷酸6-脱氧-6-N-（2-萘-2-基乙酰胺）-β-L-吡喃半乳糖-1-基鸟苷5'-二磷酸二钠盐（1），由天然丰富的D-吡喃半乳糖通过关键中间体6-叠氮化物-1,2,3,4-四-O-苯甲酰基-6-脱氧-β-L-吡喃半乳糖有效地合成（10）。结果表明，糖基供体1和丹磺化受体底物唾液酸-α2,3-LacNAc衍生物（2）的联合使用使我们能够对唾液酸化路易斯的产生进行高度敏感，直接和连续的体外监测X（SLe x），它由人α-1,3-岩藻糖基转移酶VI（FUT-VI）催化。动力学分析表明，化合物1是检测人FUT-VI活性的优良供体底物（KM = 0.94 microM和Vmax = 0.14 microM min（-1））。据我们所

  DOI：

  10.1002/chem.200700760
• 作为产物：
  描述：

  2,3:4,5-di-O-isopropylidene-D-galactose diethyl dithioacetal 在 吡啶 、 N-溴代丁二酰亚胺(NBS) 作用下， 以 丙酮 为溶剂， 反应 3.33h， 生成 6-O-(tert-butyldimethylsilyl)-2,3:4,5-di-O-isopropylidene-D-galactitol
  参考文献：
  名称：

  Structure–activity relationship studies on acremomannolipin A, the potent calcium signal modulator with a novel glycolipid structure 2: Role of the alditol side chain stereochemistry

  摘要：

  Five alditol analogs 1b-1f of a novel glycolipid acremomannolipin A (1a), the potential Ca2+ signal modulator isolated from Acremonium strictum, were synthesized by employing a stereoselective beta-mannosylation of appropriately protected mannose with five hexitols with different stereochemistry, and their potential on modulating Ca2+ signaling were evaluated. All these analogs were more potent compared to the original compound 1a, and proved that mannitol stereochemistry of 1a was not critical for the potent calcium signal modulating. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.12.052

文献信息

• Structure–activity relationship studies on acremomannolipin A, the potent calcium signal modulator with a novel glycolipid structure 2: Role of the alditol side chain stereochemistry
  作者：Nozomi Tsutsui、Genzoh Tanabe、Genki Gotoh、Nao Morita、Naohisa Nomura、Ayako Kita、Reiko Sugiura、Osamu Muraoka

  DOI：10.1016/j.bmc.2013.12.052

  日期：2014.2

  Five alditol analogs 1b-1f of a novel glycolipid acremomannolipin A (1a), the potential Ca2+ signal modulator isolated from Acremonium strictum, were synthesized by employing a stereoselective beta-mannosylation of appropriately protected mannose with five hexitols with different stereochemistry, and their potential on modulating Ca2+ signaling were evaluated. All these analogs were more potent compared to the original compound 1a, and proved that mannitol stereochemistry of 1a was not critical for the potent calcium signal modulating. (C) 2014 Elsevier Ltd. All rights reserved.
• FRET-Based Direct and Continuous Monitoring of Human Fucosyltransferases Activity: An Efficient synthesis of Versatile GDP-L-Fucose Derivatives from Abundantd-Galactose
  作者：Takahiro Maeda、Shin-Ichiro Nishimura

  DOI：10.1002/chem.200700760

  日期：2008.1.7

  acceptor substrate, sialyl-alpha2,3-LacNAc derivative (2) allowed us to carry out highly sensitive, direct, and continuous in vitro monitoring of the generation of sialyl Lewis X (SLe x), which is catalyzed by human alpha-1,3-fucosyltransferase VI (FUT-VI). A kinetic analysis revealed that compound 1 was an excellent donor substrate (KM=0.94 microM and Vmax=0.14 microM min(-1)) for detecting human FUT-VI

  我们已经开发了一种简便且通用的协议，用于通过使用荧光能量共振转移（FRET）连续监测人岩藻糖基转移酶的活性，并探索了其在抑制剂筛选测定中的可行性。具有荧光探针的便捷糖核苷酸6-脱氧-6-N-（2-萘-2-基乙酰胺）-β-L-吡喃半乳糖-1-基鸟苷5'-二磷酸二钠盐（1），由天然丰富的D-吡喃半乳糖通过关键中间体6-叠氮化物-1,2,3,4-四-O-苯甲酰基-6-脱氧-β-L-吡喃半乳糖有效地合成（10）。结果表明，糖基供体1和丹磺化受体底物唾液酸-α2,3-LacNAc衍生物（2）的联合使用使我们能够对唾液酸化路易斯的产生进行高度敏感，直接和连续的体外监测X（SLe x），它由人α-1,3-岩藻糖基转移酶VI（FUT-VI）催化。动力学分析表明，化合物1是检测人FUT-VI活性的优良供体底物（KM = 0.94 microM和Vmax = 0.14 microM min（-1））。据我们所