1-methyl-2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-β-D-glucopyranoside | 13223-83-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-methyl-2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-β-D-glucopyranoside
• 英文别名: methyl-[O²,O³,O⁶-triacetyl-O⁴-(tetra-O-acetyl-α-D-glucopyranosyl)-β-D-glucopyranoside]；Methyl-[O²,O³,O⁶-triacetyl-O⁴-(tetra-O-acetyl-α-D-glucopyranosyl)-β-D-glucopyranosid]；[(2R,3R,4S,5R,6R)-4,5-diacetyloxy-6-methoxy-3-[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 13223-83-1；30021-60-4；30021-61-5；32773-76-5；33054-50-1；52538-76-8；67109-89-1；67310-46-7；81307-80-4；84094-21-3；103188-88-1；114818-00-7；118493-14-4；119433-24-8；119433-25-9；119435-34-6
• 化学式: C₂₇H₃₈O₁₈
• 分子量: 650.588
• InChiKey: NWTWYNIVYAQTJI-DVCSACCXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  45
• 可旋转键数：
  19
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  221
• 氢给体数：
  0
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  1-methyl-2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-β-D-glucopyranoside 在 水 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 methyl beta-D-maltoside
  参考文献：
  名称：

  Markovic, Zoran; Predojevic, Jasmina; Manojlovic, Nedeljko T., Bulletin of the Chemical Society of Ethiopia, 2011, vol. 25, # 1, p. 83 - 90

  摘要：

  DOI：
• 作为产物：
  描述：

  2,3-Di-O-acetyl-1,6-anhydro-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-β-D-glucopyranose 在 silver carbonate 、 二乙胺基三氟化硫 、 zinc dibromide 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 1-methyl-2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-β-D-glucopyranoside
  参考文献：
  名称：

  Bock, Klaus; Pedersen, Henric, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1988, vol. 42, # 2, p. 75 - 85

  摘要：

  DOI：

文献信息

• Regio- and Chemoselective Deprotection of Primary Acetates by Zirconium Hydrides
  作者：Marine Gavel、Thibaut Courant、Antoine Yvan Philippe Joosten、Thomas Lecourt

  DOI：10.1021/acs.orglett.8b03947

  日期：2019.4.5

  A combination of DIBAL-H and Cp2ZrCl2 is shown to promote the regioselective cleavage of primary acetates on a broad scope of substrates, ranging from carbohydrates to terpene derivatives, with a high tolerance toward protecting groups and numerous functionalities found in natural products and bioactive compounds. Apart from providing highly valuable building blocks in only two steps from biosourced raw materials, this selective de-O-acetylation should also be strongly helpful to solve selectivity issues in organic synthesis.
• SN²Displacement of Carbohydrate Triflates by 9-Oximes of Erythromycin A and Of a Tylosin Derivative
  作者：Cyrille Grandjean、Gabor Lukacs

  DOI：10.1080/07328309608005695

  日期：1996.9

  The preparation of 9-O-glycosyloxime derivatives of erythromycin A (1) and tylosin (2) is reported. Access to this new class of macrolides was achieved from (E)-9-oxime of erythromycin A (3) and 9-oxime of tylosin 20-(1,3-dithiane) (4), by successful displacement of triflates of suitably protected carbohydrates.
• A convenient large-scale synthesis of methyl α-maltoside: a simple model for amylose
  作者：Stuart J. Gebbie、Ian Gosney、Paul R. Harrison、Isabelle M.F. Lacan、William R. Sanderson、J.Phillip Sankey

  DOI：10.1016/s0008-6215(98)00110-4

  日期：1998.4

  Methyl 4-O-(alpha-D-glucopyranosyl)-alpha-D-glucopyran (methyl alpha-maltoside), a model compound for amylose, has been synthesized in four steps and 63% overall yield from relatively inexpensive D-(+)-maltose. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Markovic, Zoran; Predojevic, Jasmina; Manojlovic, Nedeljko T., Bulletin of the Chemical Society of Ethiopia, 2011, vol. 25, # 1, p. 83 - 90
  作者：Markovic, Zoran、Predojevic, Jasmina、Manojlovic, Nedeljko T.

  DOI：——

  日期：——
• Bock, Klaus; Pedersen, Henric, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1988, vol. 42, # 2, p. 75 - 85
  作者：Bock, Klaus、Pedersen, Henric

  DOI：——

  日期：——