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

HRID 468225Notes

Reaction equation

HRID 468225 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-82680ab05ffc4c89a429280a36dfb12a
Source dataset
uspto-grants-2014_01
Patent number
US08624006B2

Reaction notes

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