2,4,6-tri-O-benzyl-3-deoxy-D-erythro-hex-2-enonolactone | 62641-00-3

• 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: 2,4,6-tri-O-benzyl-3-deoxy-D-erythro-hex-2-enonolactone
• 英文别名: 2,4,6-tri-O-benzyl-3-deoxy-D-erythro-hex-2-enono-1,5-lactone；<4S,5R>-2,4,6-tribenzyloxy-5-hydroxyhex-2-enoic acid-1,5-lactone；3-deoxy-2,4,6-tri-O-benzyl-D-erythro-hex-2-enono-1,5-lactone；2,4,6-tri-O-benzyl-3-deoxy-D-erythro-hex-2-enone-1,5-lactone；(2R,3S)-3,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-2,3-dihydropyran-6-one
• CAS: 62641-00-3
• 化学式: C₂₇H₂₆O₅
• 分子量: 430.5
• InChiKey: QPAQKOOYCGTMIE-AZGAKELHSA-N

物化性质

• 沸点：
  627.1±55.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,4,6-tri-O-benzyl-3-deoxy-D-erythro-hex-2-enonolactone 在 lithium aluminium tetrahydride 作用下， 生成 2,4,6-tri-O-benzyl-3-deoxy-D-erythro-hex-2-enopyranose
  参考文献：
  名称：

  与部分苄基酯合成。13.通过新型消除反应，来自2,3,4,6-四-O-苄基-N，N-二甲基-5-O-（甲基磺酰基）-D-葡糖酰胺的不饱和衍生物。

  摘要：

  DOI：

  10.1021/jo01269a024
• 作为产物：
  描述：

  2,3,4,6-四苄基-D-吡喃葡萄糖 在 sodium methylate 、 乙酸酐 、 二甲基亚砜 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 2,4,6-tri-O-benzyl-3-deoxy-D-erythro-hex-2-enonolactone
  参考文献：
  名称：

  Tsuda, Yoshisuke; Nunozawa, Tetsuji; Yoshimoto, Kimihiro, Chemical and pharmaceutical bulletin, 1980, vol. 28, # 11, p. 3223 - 3231

  摘要：

  DOI：

文献信息

• The Synthesis of Carbohydrate α-Amino Acids Utilizing the Corey - Link Reaction
  作者：Adrian Scaffidi、Brian W. Skelton、Robert V. Stick、Allan H. White

  DOI：10.1071/ch04015

  日期：——

  Various carbohydrate ketones (uloses) have been treated with chloroform under strongly basic conditions to yield trichloromethyl tertiary alcohols. These alcohols, when subjected to the conditions of the modified Corey–Link reaction (sodium azide and 1,8-diazabicyclo[5.4.0]undec-7-ene in methanol), generally gave the expected azido ester with complete stereocontrol. Subsequent transformations on these

  已在强碱性条件下用氯仿处理各种碳水化合物酮（乌洛糖）以产生三氯甲基叔醇。这些醇在经受改进的 Corey-Link 反应条件（叠氮化钠和甲醇中的 1,8-二氮杂双环[5.4.0] undec-7-ene）条件下，通常会产生具有完全立体控制的预期叠氮基酯。这些叠氮基酯的后续转化提供了氨基酯、叠氮基酸，在一种情况下还提供了氨基酸。应用于受保护的 d-glucono-1,5-lactone 的类似序列仅部分成功。据报道 1,2:5,6-di-O-isopropylidene-3-C-trichloromethyl 的单晶 X 射线结构-α-d-阿洛糖，(3S)-3-C-azido-3-C-carboxy-3-deoxy-1,2:5,6-di-O-isopropylidene-α-d-ribo-hexose, 1 ,2:5,6-di-O-cyclohexylidene-3-C-trichloromethyl-α-d-gulose
• PREPARATION AND REACTIVITY OF SOME 3-DEOXY-<scp>D</scp>-ALTRONIC ACID DERIVATIVES
  作者：María de Gracia García-Martín、María Violante de Paz Báñez、Juan A. Galbis

  DOI：10.1081/car-100103954

  日期：2001.3.31

  3-Amino-3-deoxy-2,4,5,6-tetra-O-methyl-D-altronic acid hydrochloride was the key intermediate in the preparation of poly[(2S,3R)-2-methoxy-3-(D-erythro-trimethoxypropyl)propanamide], a chiral nylon 3 analog. We now describe an alternative synthetic route to this amino acid and the unexpected reactivity of some of its 3-deoxy derivatives. Attempts to open the 3-azido-3-deoxy-tri-O-methyl (or O-benzyl)-D-altrono-1

  3-氨基-3-脱氧-2,4,5,6-四-O-甲基-D-丙二酸盐酸盐是制备聚[（2 S，3 R）-2-甲氧基-3]的关键中间体-（D-赤型-三甲氧基丙基）丙酰胺]，手性尼龙3类似物。现在，我们描述了该氨基酸的替代合成路线及其某些3-脱氧衍生物的出乎意料的反应性。尝试打开3-叠氮基-3-脱氧-三-O-甲基（或O-苄基）-D -altrono-1,5-内酯中间体得到产物的混合物，主要是α，β-不饱和羰基化合物。
• Easy access to C-glycosides from aldonolactones by a Claisen-type chain-extension reaction
  作者：René Csuk、Martin Kühn、Dieter Ströhl

  DOI：10.1016/s0040-4020(96)01079-4

  日期：1997.1

  Chain elongated 2,4-diuloses 2, 4, 6, 9–11, 24, 25 were conveniently obtained from the corresponding aldonolactones 1, 3, 5 by their reaction with carbonyl compounds in the presence of sodium hydride. These hemiacetalic products can be transformed into C-glycosides by deoxygenation with Et3SiH/BF3·Et2O.

  链伸长2,4- diuloses 2，4，6，9-11，24，25被方便地从对应aldonolactones得到1，3，5可以通过与在氢化钠的存在下羰基化合物反应。这些半缩醛产物可通过用Et 3 SiH / BF 3 ·Et 2 O脱氧而转化为C-糖苷。
• C-2 Epimerization of aldonolactones promoted by magnesium iodide: a new way towards non-enzymatic epimerization
  作者：Julie Gratien、Marie-Pierre Heck、Charles Mioskowski

  DOI：10.1016/j.carres.2007.10.006

  日期：2008.1

  The first example of a non-enzymatic C-2 epimerization of aldonolactones is reported. The reaction of 2,3,4,6-tetra-O-benzyl-D-gluconolactone or 2,3,4,6-tetra-O-benzyl-D-mannonolactone with MgI2 in EtOH afforded their respective C-2 epimer. Studies conducted in EtOD showing the incorporation of a deuterium atom only at the C-2 position of the epimerized product reveal an epimerization rather than a racemization reaction. A mechanism involving a chelation with a magnesium species is proposed to explain this C-2 inversion reaction. (c) 2007 Elsevier Ltd. All rights reserved.
• Rosenblum, Stuart B.; Bihovsky, Ron, Journal of the American Chemical Society, 1990, vol. 112, # 7, p. 2746 - 2748
  作者：Rosenblum, Stuart B.、Bihovsky, Ron

  DOI：——

  日期：——