benzyl ((2R,4aR,6S,7R,8R,8aS)-8-hydroxy-6-methoxy-2-phenyl hexahydropyrano[3,2-d][1,3]dioxin-7-yl)carbamate | 93000-10-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: benzyl ((2R,4aR,6S,7R,8R,8aS)-8-hydroxy-6-methoxy-2-phenyl hexahydropyrano[3,2-d][1,3]dioxin-7-yl)carbamate
• 英文别名: methyl 4,6-O-benzylidene-2-(benzyloxycarbonyl)amino-2-deoxy-α-D-glucopyranoside；benzyl N-[(2R,4aR,6S,7R,8R,8aS)-8-hydroxy-6-methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]carbamate
• CAS: 93000-10-3
• 化学式: C₂₂H₂₅NO₇
• 分子量: 415.443
• InChiKey: VDRLHQYZSHYIIK-UFOPBENGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  95.5
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  benzyl ((2R,4aR,6S,7R,8R,8aS)-8-hydroxy-6-methoxy-2-phenyl hexahydropyrano[3,2-d][1,3]dioxin-7-yl)carbamate 在 barium dihydroxide 、 溶剂黄146 、 barium(II) oxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 methyl 2--3-O-benzyl-2-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  合成证实了抗生素Tü1718 B的修饰结构

  摘要：

  二肽抗生素涂1718 B的修改后的结构物通过的-L-缬氨酰基dihydroxylysine的两种可能的非对映体的合成确认2。合成产物和天然产物的NMR光谱比较表明，天然产物的（2S，3S，5S）-或（2S，3R，5S）-构型。

  DOI：

  10.1016/s0040-4039(00)60720-7
• 作为产物：
  描述：

  2-benzyloxycarbonylamino-2-deoxy-D-glucose 在 盐酸 、 对甲苯磺酸 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 生成 benzyl ((2R,4aR,6S,7R,8R,8aS)-8-hydroxy-6-methoxy-2-phenyl hexahydropyrano[3,2-d][1,3]dioxin-7-yl)carbamate
  参考文献：
  名称：

  Regioselective sulfamoylation at low temperature enables concise syntheses of putative small molecule inhibitors of sulfatases

  摘要：

  一种据称的Sulf-2抑制剂从D-葡萄糖胺中改进的合成方法被描述，该化合物及其类似物的测定数据显示对Sulf-2、磺酶ARSA或ARSB的抑制作用较弱。

  DOI：

  10.1039/c5ob00211g

文献信息

• 一种磺达肝癸钠单糖中间体的制备方法
  申请人：江苏美迪克化学品有限公司

  公开号：CN109369738B

  公开（公告）日：2021-03-30

  本发明公开了一种磺达肝癸钠单糖中间体的制备方法，以C4位和C6位保护的氨基葡萄糖为原料，通过甲基化、酰胺化、苄基化，得到甲基3‑O‑苄基‑4,6‑O‑苄亚基‑2‑(苄氧基羰基)氨基‑2‑脱氧‑α‑D‑吡喃葡萄糖苷，然后再经过脱羟基保护基保护反应得到磺达肝癸钠单糖片段中间体甲基3‑O‑苄基‑2‑(苄氧基羰基)氨基‑2‑脱氧‑α‑D‑吡喃葡萄糖苷。该制备方法工艺简洁，副反应杂质少，收率高，适用于工艺放大制备以满足磺达肝癸钠工业化生产。
• Synthetic methods for the preparation of basic - and -pseudo-sugars. Synthesis of carbocyclic analogues of -acetyl-muramyl--alanyl--isoglutamine (MDP)
  作者：Derek H.R. Barton、S. Augy-Dorey、J. Camara、P. Dalko、J.M. Delaumény、S.D. Géro、B. Quiclet-Sire、P. Stütz

  DOI：10.1016/s0040-4020(01)97594-5

  日期：1990.1

  been transformed by Ferrier rearrangement reaction into amino-cyclohexanones 11 12 and 23 24. Reduction of ketone 11 with tri-t-butoxy-aluminium hydride followed by sequential acetylation and hydrogenolysis gave the acid 14 which was coupled with dipeptide 15 to provide 16. Alkaline hydrolysis of the latter afforded 1 a carbocyclic nor-analogue of MDP. The second target molecule 2 was prepared from

  容易从D-葡糖胺精制的两种环外烯烃10和22已经通过Ferrier重排反应转化为氨基-环己酮11 12和23 24。用三叔丁氧基铝氢化物还原酮11，然后依次进行乙酰化和氢解，得到酸14，将其与二肽15偶联，得到16。后者的碱性水解得到1 MDP的碳环或类似物。第二目标分子2由恶唑烷-假-D-葡糖胺27制备通过用甲氧基亚甲基三苯基磷烷和乙酸汞-硼氢化钠试剂处理氨基-环己酮23，可得到合成中的关键步骤。另一方面，烯烃31的硼氢化产生了假L-氨基胺衍生物28。桦木还原27，然后用（S）-α-氯丙酸依次进行亚苄基醚化，生成的36与二肽15缩合，得到36。后者的氢解提供了MDP的碳环类似物2。
• First synthesis of anomeric sulfimides - efficient glycosyl donors
  作者：Stéphanie Cassel、Isabelle Plessis、Hans Peter Wessel、Patrick Rollin

  DOI：10.1016/s0040-4039(98)01837-1

  日期：1998.10

  Sugar-derived anomeric sulfimides were prepared in high yields from the corresponding thioglycosides and their ability to act as glycosyl donors was investigated. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Adverse effects of alkali and acid on the anticoagulant potency of heparin, evaluated with methyl 2-deoxy-2-sulf- amino-α-d-glucopyranoside 3-sulfate as a model compound
  作者：Zhengchun Liu、Arthur S. Perlin

  DOI：10.1016/s0008-6215(00)90546-9

  日期：1992.4

  A variety of chemical modifications can induce a reduction in the anticoagulant activity of heparin. Among such modifications are the removal in alkaline solution of the 2-O-sulfonate group of alpha-L-idopyranosyluronic acid 2-sulfate residues (1) and, in a weakly acidic medium, of the N-sulfonate group of residues of 2-deoxy-2-sulfamino-alpha-D-glucopyranose 6-sulfate (2). This study examined the possibility that the losses in anticoagulant potency are related to a concomitant removal of the 3-O-sulfonate group of residues of 2-deoxy-2-sulfamino-alpha-D-glucopyranose 3,6-disulfate (6) in the AT-III binding site. It entailed a synthesis of methyl 2-deoxy-2-sulfamino-alpha-D-glucopyranoside 3-sulfate (7), as a model compound that was subjected to both the strongly alkaline and weakly acidic conditions appropriate for the modification of residues 1 and 2, respectively. The 3-sulfate group of 7 was found to be highly stable in both environments. This indicated that the adverse effects that these conditions have on the anticoagulant properties of heparin are not specifically associated with the 3-sulfate substituent of residues of 6 in the polymer.
• Regioselective sulfamoylation at low temperature enables concise syntheses of putative small molecule inhibitors of sulfatases
  作者：Duncan C. Miller、Benoit Carbain、Gary S. Beale、Sari F. Alhasan、Helen L. Reeves、Ulrich Baisch、David R. Newell、Bernard T. Golding、Roger J. Griffin

  DOI：10.1039/c5ob00211g

  日期：——

  An improved synthesis from d-glucosamine of a purported Sulf-2 inhibitor is described, with assay data for this compound and analogues showing only weak inhibition of Sulf-2, and sulfatases ARSA or ARSB.

  一种据称的Sulf-2抑制剂从D-葡萄糖胺中改进的合成方法被描述，该化合物及其类似物的测定数据显示对Sulf-2、磺酶ARSA或ARSB的抑制作用较弱。