tartaric acid benzylidene acetal | 83529-41-3

• 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: tartaric acid benzylidene acetal
• 英文别名: (R,R)-Benzylidenetartaric acid；(4R,5R)-2-phenyl-1,3-dioxolane-4,5-dicarboxylic acid
• CAS: 83529-41-3
• 化学式: C₁₁H₁₀O₆
• 分子量: 238.197
• InChiKey: HABDQSBRZYXMHH-HTQZYQBOSA-N

物化性质

• 沸点：
  507.4±50.0 °C(predicted)
• 密度：
  1.493±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tartaric acid benzylidene acetal 在 Grubbs catalyst first generation 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (E)-(3aR,13aR)-2-Phenyl-3a,6,7,10,11,13a-hexahydro-1,3,5,12-tetraoxa-cyclopentacyclododecene-4,13-dione
  参考文献：
  名称：

  A Strategy for Macrocyclic Ring Closure and Functionalization Aimed toward Split-Pool Syntheses

  摘要：

  DOI：

  10.1021/ja992658m
• 作为产物：
  描述：

  dimethyl 2,3-O-benzylidene-L-tartrate 、 氢氧化钾 以89%的产率得到
  参考文献：
  名称：

  ROUSH, WILLIAM R.;BANFI, LUCA, J. AMER. CHEM. SOC., 110,(1988) N 12, 3979-3982

  摘要：

  DOI：

文献信息

• [EN] GLUCOSE-SENSITIVE PEPTIDE HORMONES<br/>[FR] HORMONES PEPTIDIQUES SENSIBLES AU GLUCOSE
  申请人：GUBRA APS

  公开号：WO2019243576A1

  公开（公告）日：2019-12-26

  The present invention relates to a conjugate of the formula P-L-I, wherein P is a peptide hormone effecting the metabolism of carbohydrates in vivo, L is a hydrolysable linker molecule consisting of Lp and Lj, and I is a molecule capable of inhibiting the effect of the peptide hormone P on the metabolism of carbohydrates in vivo. Under in vivo conditions, the conjugate is the major compound. When the concentration of glucose increases in v/vo,the concentration of the peptide hormone effecting the metabolism of carbohydrates in vivo also increases.

  本发明涉及一种公式为P-L-I的结合物，其中P是一种肽激素，在体内影响碳水化合物的代谢，L是由Lp和Lj组成的可水解的连接分子，I是一种能够抑制肽激素P对体内碳水化合物代谢影响的分子。在体内条件下，该结合物是主要化合物。当葡萄糖浓度在v/vo中增加时，影响体内碳水化合物代谢的肽激素浓度也会增加。
• N,N'-Bis(2,2,2-trifluoroethyl)-N,N'-ethylenetartramide: An Improved Chiral Auxiliary for the Asymmetric Allylboration Reaction
  作者：William R. Roush、Paul T. Grover

  DOI：10.1021/jo00117a036

  日期：1995.6

  N,N-Bis(2,2,2-trifluoroethyl)-N,N'-ethylenetartramide (8), synthesized by a simple four-step sequence from ethylenediamine and benzylidenetartaric acid, was designed in anticipation that the derived allylboronates 9-11 would display enhanced reactivity owing to the inductive effect of the N-trifluoroethyl substituents that would increase the Lewis acidity of the boron atom of the B-allyl-1,3,2-dioxaborolanes. Reagents 9-11 were synthesized by transesterification of 8 with the crystalline and easily purified allylboronate diethanolamine complexes 13, 19, and 25. Allylboronate 9 is ca. 100-fold more reactive than 6 and is also substantially more useful than the previously reported allyboronate 4, which suffers from very poor solubility in toluene at -78 degrees C. Most importantly, allylboronates 9-11 are significantly more enantioselective than the parent tartrate allylboronates 1-3 and rank among the most highly enantioselective allylboron reagents yet reported. Reactions of 9-11 with aldehydes are performed in THF at- -78 or -55 degrees C for 5-12 h periods. The enantioselectivity realized in reactions with achiral aldehydes is 92-95% ee (Table 2), and excellent diastereoselectivity is achieved in double asymmetric reactions with chiral aldehydes 15a, 15b, and 33 (Tables 3 and 4). For example, 16 and 28 are now available with a minimum selectivity of 92% from reactions of 15a and 15b with allylboronate 9, while the crotylboration products 29, 30, and 31 are available with a minimum selectivity of 90% (usually greater than or equal to 95%) from reactions of 15a and 15b with crotylboronates 10 and 11; the fourth isomer, 32a, is available with 83% selectivity. Chiral reagents 9-11 thus appear well suited for application to complex problems in organic synthesis.
• Phosphonylation of 1,3-Diaryl-2,3-dihydro1<i>H</i>-naphth[1,2-<i>e</i>][1,3]oxazine by Dialkyl and Diaryl Phosphonates
  作者：Kirill E. Metlushka、Vladimir A. Alfonsov、Charles E. McKenna、Boris A. Kashemirov、Olga N. Kataeva、Viktor F. Zheltukhin、Dilyara N. Sadkova、Alexey B. Dobrynin

  DOI：10.1080/10426500802344519

  日期：2008.10.7

  The possibility of using of easily available 1-(alpha-aminobenzyl)-2-naphthols as chiral auxiliaries in the synthesis of non-racemic alpha-aminophosphonates has been shown.
• ROUSH, WILLIAM R.;BANFI, LUCA, J. AMER. CHEM. SOC., 110,(1988) N 12, 3979-3982
  作者：ROUSH, WILLIAM R.、BANFI, LUCA

  DOI：——

  日期：——
• A Strategy for Macrocyclic Ring Closure and Functionalization Aimed toward Split-Pool Syntheses
  作者：Daesung Lee、Jason K. Sello、Stuart L. Schreiber

  DOI：10.1021/ja992658m

  日期：1999.11.1