2,3,4-tri-O-benzyl-5,6-O-isopropylidene-D-galactitol | 14506-38-8

• 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: 2,3,4-tri-O-benzyl-5,6-O-isopropylidene-D-galactitol
• 英文别名: (2S,3R,4S)-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,3,4-tris(phenylmethoxy)butan-1-ol
• CAS: 14506-38-8
• 化学式: C₃₀H₃₆O₆
• 分子量: 492.612
• InChiKey: ANROOPONPZHVOX-AUAHOFGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  36
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-benzyl-5,6-O-isopropylidene-D-galactitol 在 碳酸氢钠 、 戴斯-马丁氧化剂 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 (Z)-(7S,8R,9S)-7,8,9-Tris-benzyloxy-9-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-non-5-enoic acid
  参考文献：
  名称：

  Stereochemistry of Sagittamide A:  Prediction and Confirmation

  摘要：

  The C5-C10 relative stereochemistry of sagittamide A was predicted, with the use of the (3)J(H,H) profiles assembled from the spin-coupling constants reported in the literature. The predicted relative stereochemistry was then confirmed by a total synthesis of two relevant remote diastereomers. The absolute configuration of sagittamide A was established through a detailed H-1 NMR analysis of the two remote diastereomers, followed by doping experiments of them with the authentic natural product.

  DOI：

  10.1021/ol061582d
• 作为产物：
  描述：

  2,3,4-tri-O-benzyl-D-galactopyranoside 在 sodium tetrahydroborate 、 (+)-10-camphorsulfonic acid 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 8.0h， 生成 2,3,4-tri-O-benzyl-5,6-O-isopropylidene-D-galactitol
  参考文献：
  名称：

  Stereochemistry of Sagittamide A:  Prediction and Confirmation

  摘要：

  The C5-C10 relative stereochemistry of sagittamide A was predicted, with the use of the (3)J(H,H) profiles assembled from the spin-coupling constants reported in the literature. The predicted relative stereochemistry was then confirmed by a total synthesis of two relevant remote diastereomers. The absolute configuration of sagittamide A was established through a detailed H-1 NMR analysis of the two remote diastereomers, followed by doping experiments of them with the authentic natural product.

  DOI：

  10.1021/ol061582d

文献信息

• A synthesis of L-ribo-2-amino-1,3,4-trihydroxyeicosane from D-galactose
  作者：Roy Gigg、C. D. Warren

  DOI：10.1039/j39660001879

  日期：——

  L-arabino-1,2,3,4-Tetrahydroxyeicosane was synthesised by catalytic reduction of the product obtained from a Wittig reaction between the phosphorane derived from n-pentadecyltriphenylphosphonium bromide, and 2,3,4,5-tetra-O-benzylaldehydo-L-lyxose. The tetrahydroxyeicosane was coverted via the triphenylmethyl ether of L-ribo-2-azido-3,4-dibenzyloxy-1-hydroxyeicosane into the title compound, which is

  大号-阿糖-1,2,3,4- Tetrahydroxyeicosane通过催化还原从衍生自正膦之间的Wittig反应得到的产物的合成Ñ -pentadecyltriphenylphosphonium溴化物，和2,3,4,5-四ö -benzylaldehydo -大号-lyxose。所述tetrahydroxyeicosane被coverted通过的三苯基甲基醚大号-核糖-2-叠氮基-3,4-二苄氧基-1- hydroxyeicosane成标题化合物，其为C20-植物鞘氨醇的对映体。
• Synthesis of an imidazolo-L-lyxo-piperidinose derivative
  作者：Andrzej Frankowski、Dariusz Deredas、Jacques Streith、Théophile Tschamber

  DOI：10.1016/s0040-4020(98)00561-4

  日期：1998.7

  Imidazolo-L-lyxo-piperidinose 4 was synthesised from the D-galactose derivative 8 by two reaction sequences via removal of a terminal carbon atom stepwise incorporation of an imidazole moiety, and eventually intramolecular S(N)2 reaction to the corresponding piperidine ring. Piperidinose 4 proved to be a poor glycosidase inhibitor. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Stereochemistry of Sagittamide A:  Prediction and Confirmation
  作者：Hirofumi Seike、Indranath Ghosh、Yoshito Kishi

  DOI：10.1021/ol061582d

  日期：2006.8.1

  The C5-C10 relative stereochemistry of sagittamide A was predicted, with the use of the (3)J(H,H) profiles assembled from the spin-coupling constants reported in the literature. The predicted relative stereochemistry was then confirmed by a total synthesis of two relevant remote diastereomers. The absolute configuration of sagittamide A was established through a detailed H-1 NMR analysis of the two remote diastereomers, followed by doping experiments of them with the authentic natural product.