N,O,O-triacetyl-D-threo-C18-sphingosine | 128387-05-3

• 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: N,O,O-triacetyl-D-threo-C18-sphingosine
• 英文别名: triacetyl-D-threo-sphingosine；[(E,2R,3R)-2-acetamido-3-acetyloxyoctadec-4-enyl] acetate
• CAS: 128387-05-3
• 化学式: C₂₄H₄₃NO₅
• 分子量: 425.609
• InChiKey: LVOSRQQFQXFPAL-BEZSILKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.24
• 重原子数：
  30.0
• 可旋转键数：
  18.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  81.7
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  Acetic acid (E)-(R)-1-{(R)-2-acetoxy-1-[acetyl-(4-methoxy-benzyl)-amino]-ethyl}-hexadec-2-enyl ester 在 ammonium cerium(IV) nitrate 作用下， 生成 N,O,O-triacetyl-D-threo-C18-sphingosine
  参考文献：
  名称：

  Stereoselective synthesis of β-amino alcohols: practical preparation of all four stereomers of N-PMB-protected sphingosine from l- and d-serine

  摘要：

  Serine was efficiently converted to the N-p-methoxybenzyl (PMB) protected alpha'-amino enone derivative 6, which was reduced with Zn(BH4)(2) to the corresponding anti-beta-amino alcohol in >96% de. On the other hand, N-PMB-N-Boc-protected alpha'-amino enone derivative 8 was reduced by NaBH4 to syn-product with a diastereoselectivity of ca. 90%. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00147-0

文献信息

• Sphingolipids and Glycerolipids. Part II. Syntheses of Two Pairs of Enantiomeric C18-Sphingosines and a Palmitoyl Analogue of Gaucher Spleen Glucocerebroside.
  作者：Hirotaka SHIBUYA、Keiko KAWASHIMA、Norihiko NARITA、Masahiko IKEDA、Isao KITAGAWA

  DOI：10.1248/cpb.40.1154

  日期：——

  Sixteen kinds of chiral C4-epoxides [(-)-10a-d, (+)-10a-d, (-)-11a-d, (+)-11a-d], which are synthons in our synthetic strategy for complex lipids, have been prepared from (2Z)-2-butene-1, 4-diol (6) by employing a Sharpless asymmetric epoxidation. By using the chiral C4-epoxides [(+)-10a, (-)-10a, (-)-11a, (+)-11a] as starting compounds, two pairs of enantiomeric (D-erythro, L-erythro, D-threo, and L-threo)-C18-sphingosines (1, 2, 3, 4) have been synthesized via a regioselective ring-opening of the epoxide ring with azide anion followed by reduction of the azide group to an amino group and a Wittig reaction. Furthermore, D-erythro-C18-sphingosine (1) has been converted to a palmitoyl analogue (5a) of Gaucher spleen glucocerebroside (5) through a reaction pathway including successive condensations with palmitic acid and D-glucose.

  已合成十六种手性C4-环氧化物 [(-)-10a-d, (+)-10a-d, (-)-11a-d, (+)-11a-d]，这些化合物是我们合成复杂脂质策略中的合成子，通过使用Sharpless不对称环氧化反应，从(2Z)-2-丁烯-1, 4-二醇(6)制备而成。利用手性C4-环氧化物 [(+)-10a, (-)-10a, (-)-11a, (+)-11a] 作为起始化合物，通过环氧环的区域选择性开环反应与叠氮阴离子结合，随后将叠氮基团还原为氨基，并进行Wittig反应，合成了两对对映异构体（D-赤藓糖，L-赤藓糖，D-反式，L-反式）C18-鞘氨醇（1, 2, 3, 4）。此外，D-赤藓糖-C18-鞘氨醇（1）通过与棕榈酸和D-葡萄糖的连续缩合反应途径转化为高雪氏脾脏葡萄糖苷脂（5）的棕榈酰类似物（5a）。
• Stereoselective synthesis of trans-olefins by the copper-mediated SN2′ reaction of vinyl oxazines with Grignard reagents. Asymmetric synthesis of d-threo-sphingosines
  作者：Om V. Singh、Hyunsoo Han

  DOI：10.1016/j.tetlet.2007.01.145

  日期：2007.3

  The S(N)2' reaction of 6-vinyl-5,6-dihydro-4H-[1,3]oxazines with Grignard reagents in the presence of CuCN was studied, and high trans selectivity for the formation of double bond was observed with a variety of RMgX. The S(N)2' reaction, coupled with regioselective asymmetric aminohydroxylation reaction, provided a highly efficient route for the asymmetric synthesis of D-threo-N-acetylsphingosine.

  研究了在CuCN存在下6-乙烯基-5,6-二氢-4H- [1,3]恶嗪与Grignard试剂的S（N）2'反应，并观察到形成双键的高反选择性与各种RMgX。S（N）2'反应，与区域选择性不对称氨基羟基化反应相结合，为D-苏-N-乙酰基鞘氨醇的不对称合成提供了一条高效途径。
• Synthesis of two pairs of enantiomeric C18-sphingosines
  作者：Hirotaka Shibuya、Keiko Kawashima、Masahiko Ikeda、Isao Kitagawa

  DOI：10.1016/s0040-4039(01)93935-8

  日期：1989.1
• Enantiopure aminotriol from d-isoascorbic acid synthesis of
  作者：Arounarith Tuch、Michèle Sanière、Yves Le Merrer、Jean-Claude Depezay

  DOI：10.1016/0957-4166(96)00087-0

  日期：1996.3

  Enantiopure suitably N,O-protected aminotriol has been prepared from D-isoascorbic acid. The utility of this homochiral building block in the synthesis of (2R,3R)-D-threo-C-18-sphingosine is described via a Wittig reaction on a N,O-protected beta-amino-alpha-hydroxyaldehyde. (C) 1996 Elsevier Science Ltd
• SHIBUYA, HIROTAKA;KAWASHIMA, KEIKO;IKEDA, MASAHIKO;KITAGAWA, ISAO, TETRAHEDRON LETT., 30,(1989) N1, C. 7205-7208
  作者：SHIBUYA, HIROTAKA、KAWASHIMA, KEIKO、IKEDA, MASAHIKO、KITAGAWA, ISAO

  DOI：——

  日期：——