methyl 2-acetamido-2-deoxy-3,6-di-O-pivaloyl-α-D-glucopyranoside | 120489-33-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-acetamido-2-deoxy-3,6-di-O-pivaloyl-α-D-glucopyranoside
• 英文别名: [(2R,3S,4R,5R,6S)-5-acetamido-4-(2,2-dimethylpropanoyloxy)-3-hydroxy-6-methoxyoxan-2-yl]methyl 2,2-dimethylpropanoate
• CAS: 120489-33-0
• 化学式: C₁₉H₃₃NO₈
• 分子量: 403.473
• InChiKey: MBOCXFKGIJZZBE-RYPNDVFKSA-N

物化性质

• 沸点：
  538.6±50.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.77
• 重原子数：
  28.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  120.39
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  methyl 2-acetamido-2-deoxy-3,6-di-O-pivaloyl-α-D-glucopyranoside 生成 2,2-Dimethyl-propionic acid (2R,3S,4R,5R,6S)-3-acetoxy-5-acetylamino-2-(2,2-dimethyl-propionyloxymethyl)-6-methoxy-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  LJEVAKOVIC, DURDICA;TOMIC, SRDANKA;TOMASIC, JELKA, CARBOHYDR. RES., 182,(1988) N 2, C. 197-205

  摘要：

  DOI：
• 作为产物：
  描述：

  甲基 2-乙酰氨基-2-脱氧-alpha-D-吡喃葡萄糖苷 生成 methyl 2-acetamido-2-deoxy-3,6-di-O-pivaloyl-α-D-glucopyranoside
  参考文献：
  名称：

  LJEVAKOVIC, DURDICA;TOMIC, SRDANKA;TOMASIC, JELKA, CARBOHYDR. RES., 182,(1988) N 2, C. 197-205

  摘要：

  DOI：

文献信息

• Selective pivaloylation of 2-acetamido-2-deoxy sugars
  作者：Đurđica Ljevaković、Srdanka Tomić、Jelka Tomašić

  DOI：10.1016/0008-6215(88)84003-5

  日期：1988.11

  Selective pivaloylation of 2-acetamido-2-deoxy-D-glucose, its methyl alpha- and beta-glycosides, and the methyl alpha-glycoside of N-acetyl-D-muramic acid under various conditions has been studied. The structures of the products were established by 1H-n.m.r. spectroscopy and acetylation. The orders of acylation, HO-6 greater than HO-3 greater than HO-1 greater than HO-4 for 2-acetamido-2-deoxy-D-glucose

  已经研究了在各种条件下2-乙酰氨基-2-脱氧-D-葡萄糖，其甲基α-和β-糖苷以及N-乙酰基-D-山梨酸的甲基α-糖苷的选择性聚乙烯醇化。通过1H-nmr光谱和乙酰化确定产物的结构。酰化的顺序是：对于2-乙酰氨基-2-脱氧-D-葡萄糖，HO-6大于HO-3大于HO-1大于HO-1，对于HO2大于HO-4大于HO-3。建立了它的甲基糖苷。2-乙酰氨基-2-脱氧-3,6-二-O-新戊酰-吡喃葡萄糖苷和2-乙酰氨基-2-脱氧-1,3,4,6-四-O-新戊酰甲基-D-吡喃葡萄糖被兔血清酯酶水解。
• Partial purification of esterases from rabbit serum and their use in regioselective deacylations of sugars
  作者：Srđanka Tomić、Anđa Treščec、Đurđica Ljevaković、Jelka Tomašić

  DOI：10.1016/0008-6215(91)80122-4

  日期：1991.3

  14C-Labelled methyl 2,6-di-O-pivaloyl-alpha-D-glucopyranoside was used as a substrate for the detection of esterase activity in the isolation of esterase II from rabbit serum. On treatment of methyl 2,6-di-O-pivaloyl-alpha-D-glucopyranoside with rabbit serum and esterase II, the 6-O-pivaloyl group was removed selectively. Likewise, the 6-O-pivaloyl group was removed selectively from methyl 2-acetamido-2-deoxy-3

  从兔血清中分离酯酶II时，将14C-Labelled甲基2,6-二-O-新戊酰基-α-D-吡喃葡萄糖苷用作检测酯酶活性的底物。用兔血清和酯酶Ⅱ处理甲基2，6-二-O-新戊酰基-α-D-吡喃葡萄糖苷时，有选择地去除了6-O-新戊酰基。同样地，从2-乙酰氨基-2-脱氧-3,4,6-三-O-新戊酰基-α-D-吡喃葡萄糖苷甲基中选择性地除去6-O-新戊酰基。
• Stereoselective hydrolysis of radiolabelled O-pivaloyl derivatives of methyl 2-acetamido-2-deoxy-d-glucopyranoside
  作者：Srđanka Tomić、Đurđica Ljevaković、Jelka Tomašić

  DOI：10.1016/0008-6215(89)84075-3

  日期：1989.6
• In vitro sulfation of N-acetyllactosaminide by soluble recombinant human β-Gal-3′-sulfotransferase
  作者：P. Greimel、Sabrina Jabs、Stefan Storch、Slim Cherif、Koichi Honke、Thomas Braulke、Joachim Thiem

  DOI：10.1016/j.carres.2006.02.006

  日期：2006.5

  Membrane-bound beta-Gal-3'-sulfotransferase (GP3ST) was expressed and used for in vitro sulfation of Tamm-Horsfall glycoprotein. Further, the regioselective transfer of sulfate to an N-acetyllactosamine derivative could be realised with soluble chimeric GMT, also in combination with Lac transglycosylation by means of beta-galactosidase. Two alternative straightforward chemical syntheses for the target compound could be elaborated. (c) 2006 Elsevier Ltd. All rights reserved.