D-glycero-D-gulo-heptose | 6946-18-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: D-glycero-D-gulo-heptose
• 英文别名: D-glycero-D-gulo-heptopyranose；(3R,4R,5R,6R)-6-[(1R)-1,2-dihydroxyethyl]oxane-2,3,4,5-tetrol
• CAS: 6946-18-5
• 化学式: C₇H₁₄O₇
• 分子量: 210.184
• InChiKey: BGWQRWREUZVRGI-XJWWOKRRSA-N

物化性质

• 熔点：
  >95°C (dec.)
• 沸点：
  504.3±50.0 °C(Predicted)
• 密度：
  1.810±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于甲醇（轻微加热）、水（轻微）

计算性质

• 辛醇/水分配系数(LogP)：
  -3.2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  131
• 氢给体数：
  6
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  D-glycero-D-gulo-heptose 在 sodium periodate 、 Amberlite IR 120(H(+)) resin 、 barium carbonate 作用下， 反应 28.0h， 生成 methyl β-D-gulo-hexodialdo-1,5-pyranoside
  参考文献：
  名称：

  Synthesis of methyl α- and β-D-gulopyranosiduronic acids

  摘要：

  DOI：

  10.1016/0008-6215(80)90017-8
• 作为产物：
  描述：

  阿拉伯糖 在 indium 、 sodium methylate 、 臭氧 作用下， 以 甲醇 、 乙醇 为溶剂， 生成 D-glycero-D-gulo-heptose
  参考文献：
  名称：

  Chain Elongation of Aldoses by Indium-Mediated Coupling with 3-Bromopropenyl Esters

  摘要：

  A procedure is described for acyloxyallylation of unprotected aldoses with two functionalized reagents: 3-bromopropenyl acetate and 3-bromopropenyl benzoate. The reaction is performed in ethanol or a dioxane/water mixture in the presence of indium metal. The products are deesterified in the workup to afford unsaturated polyols, which are isolated as mixtures of two diastereomers. The major diastereomers are subjected to ozonolysis to afford new aldoses, which have been elongated by two carbon atoms compared to the starting materials. The new aldoses all have lyxo configuration at positions 2, 3, and 4.

  DOI：

  10.1021/jo051297s

文献信息

• [EN] SYNTHESIS OF POLYHYDROXYLATED ALKALOIDS<br/>[FR] SYNTHÈSE DES ALCALOÏDES POLYHYDROXYLÉS
  申请人：MNL PHARMA LTD

  公开号：WO2006008493A1

  公开（公告）日：2006-01-26

  A process for the production of a polyhydroxylated bicyclic (e.g. pyrrolizidine such as casuarine (10), indolizidine or quinolizidine) alkaloid comprises the cyclisation of a pyrrolidine or piperidine intermediate having three or more free hydroxyl groups.

  一种用于生产多羟基双环（例如吡咯里西啶，例如相思豆碱（10）、吲哚里西啶或喹诺里西啶）生物碱的过程，包括将具有三个或更多自由羟基的吡咯烷或哌啶中间体进行环合。
• The Amadori rearrangement as glycoconjugation method: Synthesis of non-natural <i>C</i>-glycosyl type glycoconjugates
  作者：Katharina Gallas、Gerit Pototschnig、Florian Adanitsch、Arnold E Stütz、Tanja M Wrodnigg

  DOI：10.3762/bjoc.8.185

  日期：——

  The Amadori rearrangement was investigated as a potential method for the conjugation of carbohydrate moieties to suitable amino components. Starting from selected aldoheptoses, which are readily available by means of the Kiliani-Fischer C-elongation reaction of the corresponding aldohexoses, glycoconjugates presenting D-gluco, D-manno and D-galacto as well as GlcNAc motifs have been synthesised. Following

  研究了 Amadori 重排作为碳水化合物部分与合适的氨基组分缀合的潜在方法。从选定的己醛糖开始，它们很容易通过相应的己醛糖的 Kiliani-Fischer C 延伸反应获得，已经合成了呈现 D-葡萄糖、D-甘露糖和 D-半乳糖以及 GlcNAc 基序的糖缀合物。遵循这一策略，可以通过非常短的合成方法获得非天然 C-糖基型糖缀合物，可用作较大分子结构的组成部分。
• The Amadori Rearrangement for Carbohydrate Conjugation: Scope and Limitations
  作者：Cornelia Hojnik、Anne Müller、Tobias-Elias Gloe、Thisbe K. Lindhorst、Tanja M. Wrodnigg

  DOI：10.1002/ejoc.201600458

  日期：2016.9

  The Amadori rearrangement was investigated for the synthesis of C‐glycosyl‐type neoglycoconjugates. Various amines including diamines, amino‐functionalized glycosides, lysine derivatives, and peptides were conjugated with two different heptoses to generate non‐natural C‐glycosyl‐type glycoconjugates of the d‐gluco and d‐manno series. With these studies, the scope and limitations of the Amadori rearrangement

  研究了 Amadori 重排以合成 C-糖基型新糖缀合物。包括二胺、氨基功能化糖苷、赖氨酸衍生物和肽在内的各种胺与两种不同的庚糖结合，生成 d-gluco 和 d-manno 系列的非天然 C-糖基型糖缀合物。通过这些研究，Amadori 重排作为结合方法的范围和局限性已经在碳水化合物底物和氨基成分方面得到了举例说明。
• The Amadori rearrangement as key reaction for the synthesis of neoglycoconjugates
  作者：Tanja M. Wrodnigg、Christiane Kartusch、Carina Illaszewicz

  DOI：10.1016/j.carres.2008.02.022

  日期：2008.8

  The Amadori rearrangement was introduced as a key step for the conjugation of carbohydrate moieties with suitable amines such as aliphatic amines and amino acid derivatives. The rearrangement products were further transformed into the corresponding 1-N,2-O cyclic carbamates employing triphosgene to obtain anomerically stable glycoconjugates. The reaction conditions were probed on a model substrate

  引入Amadori重排是将碳水化合物部分与合适的胺（例如脂肪族胺和氨基酸衍生物）缀合的关键步骤。使用三光气将重排产物进一步转化为相应的1-N，2-O环状氨基甲酸酯，以得到异性稳定的糖缀合物。在模型底物3，5-二-O-苄基-α，β-d-葡萄糖呋喃糖上探测反应条件，并进一步应用于d-甘油-d-古洛庚糖，得到“ d-葡萄糖-缀合物”。仅以高分离产率的α-异头异构体形式存在。
• Acetonides of octonolactones
  作者：Andrew A. Bell、Robert J. Nash、George W.J. Fleet

  DOI：10.1016/0957-4166(96)00043-2

  日期：1996.2

  Acetonides of the eight carbon sugar lactones, D-erythro-L-talooctono-1, 4-lactone and D-erythro-L-galactooctono-1 4-lactone, readily derived from glucoheptonolactone, are easily accessible intermediates for the synthesis of sugar mimics with six adjacent stereogenic centres and eight contiguous carbon atoms bearing functional groups.