Stearic Acid → (2S,3R,4R)-2-(N-stearoylamino)-octadecane-1,3,4-triol

HRID 468225ノート

反応式

HRID 468225 の反応式
[OH:1][CH2:2][C@@H:3]([C@@H:5]([C@@H:7]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[OH:8])[OH:6])[NH2:4].CCN=C=NCCCN(C)C.[C:34](O)(=[O:52])[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51]>N1C=CC=CC=1.CN(C1C=CN=CC=1)C>[C:34]([NH:4][C@H:3]([C@@H:5]([OH:6])[C@H:7]([OH:8])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:2][OH:1])(=[O:52])[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51]

参加物

6

反応物 3

HCID 5281Stearic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 122121Phytosphingosine

生成物 1

HCID 72190310(2S,3R,4R)-2-(N-stearoylamino)-octadecane-1,3,4-triol収率 68%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 1049Pyridine溶媒

実験手順

To a solution of phytosphingosine (99 mg, 0.31 mmol) in pyridine (3 mL) was added EDCI (128 mg, 0.66 mmol) and DMAP (cat.). Under stirring, stearic acid (90 mg, 0.31 mmol, in 15 mL CH2Cl2) was added dropwise over a period time of 16 h. The reaction was stirred under argon for 24 h at rt. Solvent was evaporated and the residue was applied to silica gel column chromatography (CHCl3:MeOH=88:12, Rf=0.35) to afford 9 as a white powder (120 mg, 68%). 1H NMR (600 MHz, CDCl3:CD3OD=90:10) δ 0.74 (t, J=7.2 Hz, 6H), 1.11-1.64 (m, 52), 1.31-1.58 (m, 4H), 2.07 (d, J=7.8 Hz, 2H), 3.40 (m, 2H), 3.55 (dd, J=11.4, 5.4 Hz, 1H), 3.64 (dd, J=11.4, 3.6 Hz, 2H). 13C NMR (150 MHz, CDCl3:CD3OD=90:10) δ 13.9, 22.6, 25.8, 25.9, 29.3, 29.4, 29.5, 29.6, 29.7, 29.8, 29.9, 31.9, 33.1, 36.6, 52.1, 61.2, 72.6, 75.8, 174.7. ESIMS calc'd for C36H73NNaO4 [M+Na]+ 606.54. found: 606.54.

後処理

  1. stirringThe reaction was stirred under argon for 24 h at rt
  2. customSolvent was evaporated

出典と根拠

ORDレコード
ord-82680ab05ffc4c89a429280a36dfb12a
出典データセット
uspto-grants-2014_01
特許番号
US08624006B2

反応ノート

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