(2R,3R,4R,5S,6R)-5-Acetylamino-4-benzyloxy-3-phenylselanyl-2-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethoxy)-6-((1S,2R)-1,2,3-tris-benzyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester | 116096-69-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4R,5S,6R)-5-Acetylamino-4-benzyloxy-3-phenylselanyl-2-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethoxy)-6-((1S,2R)-1,2,3-tris-benzyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester
• 英文别名: methyl (2R,3R,4R,5S,6R)-5-acetamido-4-phenylmethoxy-3-phenylselanyl-2-[[(1S,2R,6R,8R,9S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-8-yl]methoxy]-6-[(1S,2R)-1,2,3-tris(phenylmethoxy)propyl]oxane-2-carboxylate
• CAS: 116096-69-6
• 化学式: C₅₈H₆₇NO₁₄Se
• 分子量: 1081.13
• InChiKey: DURYRMSFPMBGBJ-JOEBIJPNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.96
• 重原子数：
  74.0
• 可旋转键数：
  22.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  156.93
• 氢给体数：
  1.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,5S,6R)-5-Acetylamino-4-benzyloxy-3-phenylselanyl-2-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethoxy)-6-((1S,2R)-1,2,3-tris-benzyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester 生成 [methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-β-D-galacto-2-nonulopyranosonate]-(2->6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose
  参考文献：
  名称：

  An efficient approach to streoselective glycosylation of N-acetylneuraminic acid: Used of phenylselenyl group as a stereocontrolling auxillary

  摘要：

  DOI：

  10.1016/s0040-4039(00)61852-x
• 作为产物：
  描述：

  benzeneselenenyl acetate 在 二乙胺基三氟化硫 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 三正丁基锡三氟基磺酸盐 作用下， 以 四氯化碳 、 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 16.5h， 生成 (2R,3R,4R,5S,6R)-5-Acetylamino-4-benzyloxy-3-phenylselanyl-2-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethoxy)-6-((1S,2R)-1,2,3-tris-benzyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  An efficient approach to streoselective glycosylation of N-acetylneuraminic acid: Used of phenylselenyl group as a stereocontrolling auxillary

  摘要：

  DOI：

  10.1016/s0040-4039(00)61852-x

文献信息

• Highly stereoselective glycosylation of sialic acid aided by stereocontrolling auxiliaries
  作者：Yukishige Ito、Tomoya Ogawa

  DOI：10.1016/s0040-4020(01)97586-6

  日期：1990.1

  .alpha.-Selective glycosylation of sialic acid was achieved by using a sialic acid donor which carries a stereocontrolling auxiliary such as selenide or sulfide group at C-3 position.
• ITO, YUKISHIGE;OGAWA, TOMOYA, TETRAHEDRON, 46,(1990) N, C. 89-102
  作者：ITO, YUKISHIGE、OGAWA, TOMOYA

  DOI：——

  日期：——
• ITO, YUKISHIGE;OGAWA, TOMOYA, TETRAHEDRON LETT., 28,(1987) N 49, 6221-6224
  作者：ITO, YUKISHIGE、OGAWA, TOMOYA

  DOI：——

  日期：——