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

HRID 468225노트

반응식

HRID 468225 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 1049Pyridine용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-82680ab05ffc4c89a429280a36dfb12a
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08624006B2

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