methyl 2,3-dideoxy-2-N-morpholino-4,6-O-(phenylmethylene)-3-C-phenylsulfonyl-β-D-glucopyranoside | 273921-18-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3-dideoxy-2-N-morpholino-4,6-O-(phenylmethylene)-3-C-phenylsulfonyl-β-D-glucopyranoside
• 英文别名: 4-[(2R,4aR,6R,7S,8R,8aR)-8-(benzenesulfonyl)-6-methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]morpholine
• CAS: 273921-18-9
• 化学式: C₂₄H₂₉NO₇S
• 分子量: 475.563
• InChiKey: DPAXXCZECAXHAH-TZNXUKFXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  91.9
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 2,3-dideoxy-2-N-morpholino-4,6-O-(phenylmethylene)-3-C-phenylsulfonyl-β-D-glucopyranoside 在 magnesium 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以47%的产率得到methyl 2,3-dideoxy-2-N-morpholino-4,6-O-(phenylmethylene)-β-D-ribo-hexopyranoside
  参考文献：
  名称：

  Vinylsulfone-modified carbohydrates: first general route to d-lividosamine (2-amino-2,3-dideoxy-d-glucose) and its new analogues

  摘要：

  A general route to D-lividosamine and its new analogues has been devised for the first time. The essence of the present synthetic route lies in the diastereoselective introduction of N-monoalkylated and N-dialkylated amines to C-2 carbons of methyl 2,3-dideoxy-3-C-phenylsulfonyl-alpha -D-hex-2-enopyranoside and methyl 2,3-dideoxy-3-C-phenylsulfonyl-P-D-hex-2-enopyranoside in equatorial configurations. The 2-amino-2,3-didcoxysugrs thus generated, are desulfonated reductively at C-3 sites to produce a known intermediate for the synthesis of D-lividosamine and several new 2-N-alkylamino- acid 2-N,N-dialkylamino-2,3-dideoxy analogues. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)01081-4
• 作为产物：
  描述：

  Methanesulfonic acid (2R,4aR,6R,7R,8R,8aR)-8-benzenesulfonyl-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 2.08h， 生成 methyl 2,3-dideoxy-2-N-morpholino-4,6-O-(phenylmethylene)-3-C-phenylsulfonyl-β-D-glucopyranoside
  参考文献：
  名称：

  将胺非对映选择性地添加到乙烯基砜改性的碳水化合物中：一种高度灵活的合成新型脱氧氨基糖的方法

  摘要：

  甲基2,3-二脱氧-4,6-O-（苯基亚甲基）-3-C-苯磺酰基-α-D-赤-己基-2-烯吡喃糖苷（5α）和甲基2,3-二脱氧-4,6- O-（苯基亚甲基）-3-C-苯基磺酰基-β-D-赤型-己基-2-烯吡喃糖苷（5 beta）已与多种胺进行迈克尔加成反应，从而开发出一种用于合成新型氨基糖的新方法。化合物5α与伯胺反应生成葡萄糖衍生物，但仲胺同时生成葡萄糖（主要）和甘露（次要）异构体。另一方面，化合物5β仅产生具有伯胺和仲胺的葡糖异构体。将一些胺添加到5α和5β的立体化学过程与将胺添加到3-硝基吡喃糖中的立体化学过程显着不同。

  DOI：

  10.1021/jo991380d

文献信息

• Diastereoselective Addition of Amines to Vinyl Sulfone Modified Carbohydrates:  A Highly Flexible Methodology for the Synthesis of New Classes of Deoxyaminosugars
  作者：Bindu Ravindran、Kandasamy Sakthivel、Cheravakkattu. G. Suresh、Tanmaya Pathak

  DOI：10.1021/jo991380d

  日期：2000.5.1

  addition reaction with various amines to develop a new methodology for the synthesis of new classes of aminosugars. Compound 5 alpha reacted with primary amines to generate gluco- derivatives, but secondary amines produced both gluco- (major) and manno- (minor) isomers. Compound 5 beta, on the other hand, produced only gluco- isomers with both primary and secondary amines. The stereochemical course of addition

  甲基2,3-二脱氧-4,6-O-（苯基亚甲基）-3-C-苯磺酰基-α-D-赤-己基-2-烯吡喃糖苷（5α）和甲基2,3-二脱氧-4,6- O-（苯基亚甲基）-3-C-苯基磺酰基-β-D-赤型-己基-2-烯吡喃糖苷（5 beta）已与多种胺进行迈克尔加成反应，从而开发出一种用于合成新型氨基糖的新方法。化合物5α与伯胺反应生成葡萄糖衍生物，但仲胺同时生成葡萄糖（主要）和甘露（次要）异构体。另一方面，化合物5β仅产生具有伯胺和仲胺的葡糖异构体。将一些胺添加到5α和5β的立体化学过程与将胺添加到3-硝基吡喃糖中的立体化学过程显着不同。
• Vinylsulfone-modified carbohydrates: first general route to d-lividosamine (2-amino-2,3-dideoxy-d-glucose) and its new analogues
  作者：Bindu Ravindran、Sachin G Deshpande、Tanmaya Pathak

  DOI：10.1016/s0040-4020(00)01081-4

  日期：2001.2

  A general route to D-lividosamine and its new analogues has been devised for the first time. The essence of the present synthetic route lies in the diastereoselective introduction of N-monoalkylated and N-dialkylated amines to C-2 carbons of methyl 2,3-dideoxy-3-C-phenylsulfonyl-alpha -D-hex-2-enopyranoside and methyl 2,3-dideoxy-3-C-phenylsulfonyl-P-D-hex-2-enopyranoside in equatorial configurations. The 2-amino-2,3-didcoxysugrs thus generated, are desulfonated reductively at C-3 sites to produce a known intermediate for the synthesis of D-lividosamine and several new 2-N-alkylamino- acid 2-N,N-dialkylamino-2,3-dideoxy analogues. (C) 2001 Elsevier Science Ltd. All rights reserved.