2-O-acetyl-3,4,6-tri-O-benzyl-α-D-galactopyranose | 93495-88-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-galactopyranose
• 英文别名: [(2S,3R,4S,5S,6R)-2-hydroxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl] acetate
• CAS: 93495-88-6
• 化学式: C₂₉H₃₂O₇
• 分子量: 492.569
• InChiKey: CIYOOYKJZYSBTB-LLQHYSMESA-N

物化性质

• 沸点：
  614.6±55.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.02
• 重原子数：
  36.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  83.45
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2-O-acetyl-3,4,6-tri-O-benzyl-α-D-galactopyranose 在 ytterbium(III) triflate MS 4 Angstroem AW 300 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 19.0h， 生成
  参考文献：
  名称：

  Efficient activation of glycosyl N-(phenyl)trifluoroacetimidate donors with ytterbium(III) triflate in the glycosylation reaction

  摘要：

  The mild, moisture-stable and cheap catalyst Yb(OTf)(3) activates glycosyl N-(phenyl)trifluoroacetimidates in the stereoselective synthesis of 1,2-trans and 1,2-cis glycosides. A suitable choice of the reaction solvent led to good yields and stereoselectivity ratios. The protocol was successfully applied to acceptors and donors both exhibiting a wide range of reactivity. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(02)01124-3
• 作为产物：
  描述：

  1,2-O-(ethoxyethylidene)-α-D-galactopyranose 在 水 、 sodium hydride 、 溶剂黄146 、 苄胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-galactopyranose
  参考文献：
  名称：

  Efficient activation of glycosyl N-(phenyl)trifluoroacetimidate donors with ytterbium(III) triflate in the glycosylation reaction

  摘要：

  The mild, moisture-stable and cheap catalyst Yb(OTf)(3) activates glycosyl N-(phenyl)trifluoroacetimidates in the stereoselective synthesis of 1,2-trans and 1,2-cis glycosides. A suitable choice of the reaction solvent led to good yields and stereoselectivity ratios. The protocol was successfully applied to acceptors and donors both exhibiting a wide range of reactivity. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(02)01124-3

文献信息

• The synthesis of 2-O-α-d-galactopyranosyl-d-galactopyranose and 2-O-(2-O-α-d-galactopyranosyl-α-d-galactopyranosyl)-d-glucopyranose undeca-acetate
  作者：Bogdan Doboszewski、Aleksander Zamojski

  DOI：10.1016/0008-6215(84)85061-2

  日期：1984.9

  Abstract The synthesis of 2-O-α- d -galactopyranosyl- d -galactopyranose was accomplished by condensation of 2,3,4,6-tetra-O-benzyl-α- d -galactopyranosyl chloride with 2,2,2-trichloroethyl 3,4,6-tri-O-benzyl-α- d -galactopyranoside in the presence of mercuric cyanide. The title trisaccharide undeca-acetate was prepared by condensing 1,3,4,6-tetra-O-acetyl-2-O-(3,4,6-tri-O-acetyl-α- d -galactopyranosyl)-α-

  摘要通过2,3,4,6-四-O-苄基-α-d-吡喃半乳糖酰氯与2,2,2-三氯乙基的缩合反应合成2-O-α-d-吡喃半乳糖基-d-吡喃半乳糖在氰化汞存在下的3,4,6-三-O-苄基-α-d-吡喃半乳糖苷。通过缩合1,3,4,6-四-O-乙酰基-2-O-（3,4,6-三-O-乙酰基-α-d-吡喃半乳糖基）-α-制备标题三糖十一乙酸酯在各种糖苷化催化剂的存在下，将d-吡喃葡萄糖与2,3,4,6-四-O-苄基-α-d-吡喃半乳糖基氯或溴化物，然后进行脱苄基和乙酰化。
• WOTOVIC, ARLETTE;JACQUINET, JEAN-CLAUDE;SINAY, PIERRE, CARBOHYDR. RES., 205,(1990) C. 235-245
  作者：WOTOVIC, ARLETTE、JACQUINET, JEAN-CLAUDE、SINAY, PIERRE

  DOI：——

  日期：——