methyl 2-(acetylamino)-2,3-dideoxy-4,6-O-(phenylmethylene)-α-D-ribo-hexopyranoside | 93453-17-9

• 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: methyl 2-(acetylamino)-2,3-dideoxy-4,6-O-(phenylmethylene)-α-D-ribo-hexopyranoside
• 英文别名: methyl 2-acetamido-4,6-O-benzylidene-2,3-dideoxy-α-D-ribo-hexopyranoside；methyl 2-acetylamino-4,6-O-benzylidene-2,3-dideoxy-α-D-ribo-hexoside；Methyl 2-(Acetylamino)-2,3-dideoxy-4,6-O-[(R)-phenylmethylene]-alpha-D-ribo-hexopyranoside；N-[(2R,4aR,6S,7R,8aS)-6-methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]acetamide
• CAS: 93453-17-9
• 化学式: C₁₆H₂₁NO₅
• 分子量: 307.346
• InChiKey: YIZGXUIIXCRYJU-JKJDWNRSSA-N

物化性质

• 沸点：
  509.5±50.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2-(acetylamino)-2,3-dideoxy-4,6-O-(phenylmethylene)-α-D-ribo-hexopyranoside 在 溶剂黄146 作用下， 生成 methyl 2-acetylamino-2,3-dideoxy-α-D-ribo-hexopyranoside
  参考文献：
  名称：

  Conway, Richard J.; Nagel, Jennifer P.; Stick, Robert V., Australian Journal of Chemistry, 1985, vol. 38, # 6, p. 939 - 945

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-[methylthio(thiocarbonyl)]-α-D-glucopyranoside 在 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 0.08h， 以99%的产率得到methyl 2-(acetylamino)-2,3-dideoxy-4,6-O-(phenylmethylene)-α-D-ribo-hexopyranoside
  参考文献：
  名称：

  Synthesis of 1,4-Diaminocyclitol Antibiotics. I. Synthesis of 4′-Hydroxyfortimicin D

  摘要：

  4'-羟基类似物fortimicin D已通过4-O-乙酰基-2,6-双(2,4-二硝基苯胺基)-2,3,6-三脱氧-α-d-呋喃己糖基氯与部分保护的氨基环醇，1,2:4,5-二-N,O-羰基fortamine B的缩合反应合成，随后进行去保护。

  DOI：

  10.1246/bcsj.60.255

文献信息

• 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.
• Conway, Richard J.; Nagel, Jennifer P.; Stick, Robert V., Australian Journal of Chemistry, 1985, vol. 38, # 6, p. 939 - 945
  作者：Conway, Richard J.、Nagel, Jennifer P.、Stick, Robert V.、Tilbrook, D. Matthew G.

  DOI：——

  日期：——
• Synthesis of 1,4-Diaminocyclitol Antibiotics. I. Synthesis of 4′-Hydroxyfortimicin D
  作者：Kazuaki Kanai、Itsuki Sakamoto、Yasunobu Miyamoto、Seiichiro Ogawa、Tetsuo Suami

  DOI：10.1246/bcsj.60.255

  日期：1987.1

  The 4′-hydroxy analog of fortimicin D has been synthesized by condensation of 4-O-acetyl-2,6-bis(2,4-dinitrophenylamino)-2,3,6-trideoxy-α-d-ribo-hexopyranosyl chloride with a partially protected aminocyclitol, 1,2:4,5-di-N,O-carbonylfortamine B, followed by deprotection.

  4'-羟基类似物fortimicin D已通过4-O-乙酰基-2,6-双(2,4-二硝基苯胺基)-2,3,6-三脱氧-α-d-呋喃己糖基氯与部分保护的氨基环醇，1,2:4,5-二-N,O-羰基fortamine B的缩合反应合成，随后进行去保护。