(2R,3R,4E)-4-Icosasphingenine triacetate | 25494-35-3

• 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: (2R,3R,4E)-4-Icosasphingenine triacetate
• 英文别名: tri-acetyl-sphingosine；Triacetyl-C20-D-erythro-sphingosine；[(E,2S,3R)-2-acetamido-3-acetyloxyicos-4-enyl] acetate
• CAS: 25494-35-3
• 化学式: C₂₆H₄₇NO₅
• 分子量: 453.663
• InChiKey: AEHNYMQMGXWKFF-FRQYBFLQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.02
• 重原子数：
  32.0
• 可旋转键数：
  20.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.81
• 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：

  (2S,3R,4E)-2-氨基-4-二十碳烯-1,3-二醇 生成 (2R,3R,4E)-4-Icosasphingenine triacetate
  参考文献：
  名称：

  MORI, KENJI;MATSUDA, HIROYUKI, LIEBIGS ANN. CHEM.,(1991) N, C. 529-535

  摘要：

  DOI：

文献信息

• An efficient, stereoselective synthesis of 4-E- and 4-Z-d-erythro-sphingenine and related compounds from 2-amino-2-deoxy-d-glucose
  作者：Tamio Sugawara、Masayuki Narisada

  DOI：10.1016/0008-6215(89)85012-8

  日期：1989.12

  Efficient, stereoselective synthesis of 4-E- and 4-Z-D-erythro-sphingenines having C16, C18, and C20 carbon-chains was achieved in 13 steps, starting from allyl 2-benzyloxycarbonylamino-2-deoxy-alpha-D-glucopyranoside. 2-Amino-1,6-di-O-tert- butyldiphenylsilyl-2-N,3-O-carbonyl-2-deoxy-D -allitol was used as the key intermediate.

  从烯丙基2-苄氧基羰基氨基-2-脱氧-α-D-吡喃葡萄糖苷开始，由13个步骤完成了具有C16，C18和C20碳链的4-E-和4-ZD-赤型-鞘氨醇的高效，立体选择性合成。使用2-氨基-1,6-二-O-叔丁基二苯基甲硅烷基-2-N，3-O-羰基-2-脱氧-D-烯丙醇作为关键中间体。
• Synthesis of d-erythro-sphingosines
  作者：Richard R. Schmidt、Peter Zimmermann

  DOI：10.1016/s0040-4039(00)85510-0

  日期：1986.1

  2,4-Di-O-protected D-threose, readily available from D-galactose, is a versatile intermediate for D-erythro-ephingosine syntheses via trans-selective Wittig reaction, azide introduction at the unprotected hydroxylic group, and subsequent azide reduction.

  2,4-二-O-保护的D-苏糖，可容易地从D-半乳糖获得，是通过反式选择性Wittig反应，未保护的羟基引入叠氮化物以及随后的叠氮化物还原反应而用于D-赤型-ephingosine合成的通用中间体。 。
• Stereoselective mono- and bis-homologation of L-serinal via 2-trimethylsilylthiazole addition. The thiazole route to amino L-sugars and D-erythro-sphingosines
  作者：Alessandro Dondoni、Giancarlo Fantin、Marco Fogagnolo、Alessandro Medici

  DOI：10.1039/c39880000010

  日期：——

  anti-Addition [92% diastereoselectivity (d.s.)] of 2-trimethylsilylthiazole (2) to O,N-protected L-serinal (1) and deblocking the formyl group in the resulting adduct, leads to the (2S,3S)-2,4-dihydroxy-3-aminobutanal derivative (7), which serves as a precursor both to masked 4-amino-4-deoxy-L-ribose/L-arabinose and D-erythro-C20-sphingosine.

  2-三甲基甲硅烷基噻唑（2）对O，N保护的L-丝氨酸（1）的抗加成[92％非对映选择性（ds）]和使所得加合物中的甲酰基解封，导致（2 S，3 S） -2,4-二羟基-3-氨基丁醛衍生物（7），其用作前体既掩蔽4-氨基-4-脱氧大号核糖/大号-arabinose和d -赤-C 20 -sphingosine。
• Stereochemistry associated with the addition of 2-(trimethylsilyl)thiazole to differentially protected .alpha.-amino aldehydes. Applications toward the synthesis of amino sugars and sphingosines
  作者：Alessandro Dondoni、Giancarlo Fantin、Marco Fogagnolo、Paola Pedrini

  DOI：10.1021/jo00292a013

  日期：1990.3
• DONDONI, ALESSANDRO;FANTIN, GLIANCARLO;FOGAGNOLO, MARCO;PEDRINI, PAOLA, J. ORG. CHEM., 55,(1990) N, C. 1439-1446
  作者：DONDONI, ALESSANDRO、FANTIN, GLIANCARLO、FOGAGNOLO, MARCO、PEDRINI, PAOLA

  DOI：——

  日期：——