methyl 3,4-di-O-benzyl-2-carbamoyl-2-deoxy-α-L-arabinopyranoside | 135186-59-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3,4-di-O-benzyl-2-carbamoyl-2-deoxy-α-L-arabinopyranoside
• 英文别名: (2R,3R,4R,5S)-2-methoxy-4,5-bis(phenylmethoxy)oxane-3-carboxamide
• CAS: 135186-59-3
• 化学式: C₂₁H₂₅NO₅
• 分子量: 371.433
• InChiKey: ONZDSBSRBWQEJN-VNYTWHDVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  80
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 3,4-di-O-benzyl-2-carbamoyl-2-deoxy-α-L-arabinopyranoside 在 吡啶 、 氯化亚砜 作用下， 以 苯 为溶剂， 以76%的产率得到methyl 3,4-di-O-benzyl-2-cyano-2-deoxy-α-L-arabinopyranoside
  参考文献：
  名称：

  2-C-Carbamoyl-2, 2-C-cyano-, and 2-C-acetamidomethyl-substituted glycosides

  摘要：

  DOI：

  10.1016/0008-6215(91)84067-o
• 作为产物：
  描述：

  methyl 3,4-di-O-benzyl-2-deoxy-2-(tosylcarbamoyl)-α-L-arabinopyranoside 在 萘 、 sodium 作用下， 以 乙二醇二甲醚 为溶剂， 反应 0.17h， 以70%的产率得到methyl 3,4-di-O-benzyl-2-carbamoyl-2-deoxy-α-L-arabinopyranoside
  参考文献：
  名称：

  2-C-Carbamoyl-2, 2-C-cyano-, and 2-C-acetamidomethyl-substituted glycosides

  摘要：

  DOI：

  10.1016/0008-6215(91)84067-o

文献信息

• 2-Amino-2-deoxyglycoside Derivatives via Hofmann Rearrangement of 2-Carbamoyl-2-deoxyglycosides
  作者：Danuta Mostowicz、Czesław Bełżecki、Marek Chmielewski

  DOI：10.1055/s-1991-26443

  日期：——

  Methyl 2-methoxy- and 2-tert-butoxycarbonylamino-2-deoxyglycosides were obtained from methyl 2-carbamoyl-2-deoxyglycosides via Hofmann rearrangement with sodium methoxide/bromine/methanol or sodium hydroxide/sodium bromite/methanol or lead tetraacetate tert-butyl alcohol/dimethylformamide.

  甲基 2-氨基甲酰基-2-脱氧糖苷和甲基 2-叔丁氧羰基氨基-2-脱氧糖苷通过霍夫曼重排法与甲醇/溴化钠/甲醇或氢氧化钠/溴化钠/甲醇或四乙酸铅叔丁醇/二甲基甲酰胺反应制得。
• Formation of β-lactams fused to the pyranoid ring via the Mitsunobu reaction
  作者：O. Zegrocka、W. Abramski、Z. Urbańczyk-Lipkowska、M. Chmielewski

  DOI：10.1016/s0008-6215(98)00017-2

  日期：1998.2

  N-Tosyl-2-C-carbamoyl glycosides having the alpha-L-arabino- and beta-D-xylo- configuration form under Mitsunobu conditions 2-C:3-N-carbonyl-2,3-dideoxy-3-N-tosylamino-alpha-L-lyxo and beta-D-arabinopyranosides, respectively, having the beta-lactam ring fused to the pyranoid one; neither the formation of the gamma-lactam ring nor that of the 3,4-epoxide were observed. The gamma-lactam 2-C:4-N-carbonyl-2,4-dideoxy-4-N-tosylamino-beta-D-xylopyranoside can be obtained after protection of the 3-hydroxy group in the starting glycoside of alpha-L-arabino-configuration. The structure and configuration of methyl 2-C:3-N-carbonyl-2,3-dideoxy-3-N-tosylamino-beta-D-ribopyranoside and methyl 2-C:3-N-carbonyl-2,3-dideoxy-3-N-tosylamino-beta-D-erythro-pyranosid-4-ulose were proved by X-ray crystallography. (C) 1998 Elsevier Science Ltd. All rights reserved.
• MOSTOWICZ, DANUTA;ZEGROCKA, OLIWIA;CHMIELEWSKI, MARECK, CARBOHYDR. RES., 212,(1991) C. 283-288
  作者：MOSTOWICZ, DANUTA、ZEGROCKA, OLIWIA、CHMIELEWSKI, MARECK

  DOI：——

  日期：——