1-formyl-2,3,4,6-tetraacetyl-β-D-glucopyranoside | 83615-64-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-formyl-2,3,4,6-tetraacetyl-β-D-glucopyranoside
• 英文别名: 2,3,4,6-tetra-O-acetyl-1-formylglucopyranose；3,4,5,7-Tetra-O-acetyl-D-glycero-D-gulo-heptose；2,3,4,6-tetra-O-acetyl-2,6-anhydro-D-glycero-D-gulo-heptose；2,3,4,6-tetra-O-acetyl-β-D-glucopyranosylformaldehyde；[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-formyloxan-2-yl]methyl acetate
• CAS: 83615-64-9
• 化学式: C₁₅H₂₀O₁₀
• 分子量: 360.318
• InChiKey: NGGOLVRARHJQLH-XPABHHOTSA-N

物化性质

• 沸点：
  427.6±45.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  132
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1-formyl-2,3,4,6-tetraacetyl-β-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 、 甲苯 为溶剂， 生成 1,3-dibenzyl-2-[(2S,3S,4R,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]imidazolidine
  参考文献：
  名称：

  A convenient new route to protected and free 2,6-anhydro-d-glycero-d-gulo-heptoses (1-formyl-β-d-glucopyranosides)

  摘要：

  A new and efficient process has been developed for the synthesis of 1-formyl-beta-D-glucopyranosides frorn D-glucose. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.08.034
• 作为产物：
  描述：

  Acetic acid (2R,3R,4R,5S,6S)-3,5-diacetoxy-2-acetoxymethyl-6-((Z)-2-trimethylsilanyloxy-propenyl)-tetrahydro-pyran-4-yl ester 在 sodium periodate 、 二甲基二环氧乙烷 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 、 丙酮 为溶剂， 生成 1-formyl-2,3,4,6-tetraacetyl-β-D-glucopyranoside
  参考文献：
  名称：

  A convenient new route to protected and free 2,6-anhydro-d-glycero-d-gulo-heptoses (1-formyl-β-d-glucopyranosides)

  摘要：

  A new and efficient process has been developed for the synthesis of 1-formyl-beta-D-glucopyranosides frorn D-glucose. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.08.034

文献信息

• Synthesis of 4,8-anhydro-2,3-dideoxy-d-galacto- and -d-gluco-non-3-enose dimethyl acetal and their use as new probes for determining by 1H-n.m.r. spectroscopy the steric course of protonation by glycoside hydrolases
  作者：Hanz Fritz、Jochen Lehmann、Markus Schmidt-Schuchardt、Wolfgang Weiser

  DOI：10.1016/0008-6215(91)84092-s

  日期：1991.9

  by multistep syntheses. Addition of water to the enolic double bonds of both compounds was catalyzed only by the corresponding enzymes β- d -galactosidase from Escherichia coli , α- d -galactosidase from green coffee beans, and β- d -glucosidase from sweet almonds, α- d -glucosidase from yeast. The enzymic hydration of 2 , performed in D 2 O to analyze the steric course of the addition, gave 2,3-dideoxy-α-

  摘要通过多步合成法制备了标题非蔗糖衍生物2（d-galacto）和4-（d-葡萄糖）。仅通过来自大肠杆菌的相应酶β-d-半乳糖苷酶，来自生咖啡豆的α-d-半乳糖苷酶和来自甜杏仁的β-d-葡萄糖苷酶，α-d才将水加至这两种化合物的烯醇双键中。 -酵母中的葡萄糖苷酶。在D 2 O中进行2的酶促水合以分析加成反应的空间过程，得到2,3-二脱氧-α-d-半乳糖-（3- 2 H）-壬基-4-纤维素二甲基乙缩醛（5） ，当水解时，提供了以螺烷16和17为主要产物（85％）和稠环系统18和19为次要成分（15％）的平衡混合物。酶促水合产物的硼氢化物还原得到两种差向异构体14和15的可分离混合物，可在酸性甲醇中于62°转化8小时，分别转化为20和22。刚性的双环系统允许轻松地将单氘C-3上的构型指定为（S），从而可以确定酶催化起始步骤的空间过程，即底物中烯醇双键的氘化用过的。
• Total Synthesis of Diospyrodin and Its Three Diastereomers
  作者：Takumi Fukuda、Masanori Nagatomo、Masayuki Inoue

  DOI：10.1021/acs.orglett.0c02280

  日期：2020.8.21

  was synthesized in 13 steps. Et3B and O2 promoted the formation of an α-alkoxy carbon radical from l-ribose-derived α-alkoxyacyl telluride 5, which reacted with d-glucose-derived aldehyde 4. The radical addition realized the convergent assembly of the contiguously hydroxylated carbon-chain of 3-α and greatly contributed to streamlining the synthetic route. Compound 3-α was transformed not only to 1 but

  抗菌素双嘧啶（1）的合成步骤为13个步骤。等3乙和O 2促进的α的形成-烷氧基碳基基团从升核糖衍生的α-烷氧基酰基碲化物5，其与反应d葡萄糖衍生的醛4。自由基的加成实现了3-α的连续羟基化碳链的收敛组装，并极大地简化了合成路线。通过官能团的操纵，化合物3-α不仅被转化为1，而且被转化为其三个非对映异构体。
• Indium-Mediated Alkynylation in C-Glycoside Synthesis
  作者：Nadège Lubin-Germain、Jacques Augé、Julien Picard、Jacques Uziel

  DOI：10.1055/s-2006-926353

  日期：——

  The indium-mediated alkynylation of perbenzylated or peracetylated formylglucose is a pathway for the synthesis of various C-glycosides. Hydroxylated, ketonic, mono- or difluorinated, and methylated C-glycosides were thus obtained.

  铟介导的过苄基或过乙酰化甲酰基葡萄糖的炔化反应是合成各种 C-糖苷的途径。由此获得了羟基化、酮化、单氟化或二氟化以及甲基化的 C-糖苷。
• New and general synthesis of β-C-glycosylformaldehydes from easily available β-C-glycosylpropanones
  作者：Stéphanie Norsikian、Jennifer Zeitouni、Stéphanie Rat、Sylvie Gérard、André Lubineau

  DOI：10.1016/j.carres.2007.09.002

  日期：2007.12

  A highly effective method for the introduction of a formyl group at the anomeric position of pyranosides was developed via enolisation Of beta-C-D-glycopyranosylpropan-2-one using thermodynamic conditions then oxidative cleavage of the more substituted double bond. This sequence affords the desired aldehydes that are conveniently protected as aminals for purification and storage and easily regenerated using Dowex resin H+. In this paper, the syntheses of nine differently protected aldehydes derived from D-glucose, D-galactose. lactose and N-acetyl-D-glucosamine are presented. Our strategy proved to be very efficient in most cases excepted in the D-mannose series. (C) 2007 Elsevier Ltd. All rights reserved.
• Synthesis and reactivity of nitro sugar-derived silyl nitronates
  作者：Olivier R. Martin、Faiza E. Khamis、S. Prahlada Rao

  DOI：10.1016/s0040-4039(01)93326-x

  日期：——