Triethylamine → HCID 13799774, compound

HRID 2165883Notes

Reaction equation

HRID 2165883 reaction equation
[C:1]([O:4][C@H:5]1[C@@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:10]([O:16][C:17](=[O:19])[CH3:18])[C@@H:9]([CH2:20][O:21][C:22](=[O:24])[CH3:23])[O:8][C@@H:6]1[SH:7])(=[O:3])[CH3:2].I[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][O:32][C@H:33]1[CH2:57][CH2:56][C@@:55]2([CH3:58])[C:35](=[CH:36][CH2:37][C@@H:38]3[C@@H:54]2[CH2:53][CH2:52][C@@:51]2([CH3:59])[C@H:39]3[CH2:40][CH2:41][C@@H:42]2[C@H:43]([CH3:50])[CH2:44][CH2:45][CH2:46][CH:47]([CH3:49])[CH3:48])[CH2:34]1.C(N(CC)CC)C>ClCCl>[C:1]([O:4][C@H:5]1[C@@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:10]([O:16][C:17](=[O:19])[CH3:18])[C@@H:9]([CH2:20][O:21][C:22](=[O:24])[CH3:23])[O:8][C@@H:6]1[S:7][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][O:32][C@H:33]1[CH2:57][CH2:56][C@@:55]2([CH3:58])[C:35](=[CH:36][CH2:37][C@@H:38]3[C@@H:54]2[CH2:53][CH2:52][C@@:51]2([CH3:59])[C@H:39]3[CH2:40][CH2:41][C@@H:42]2[C@H:43]([CH3:50])[CH2:44][CH2:45][CH2:46][CH:47]([CH3:49])[CH3:48])[CH2:34]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11187637HCID 11187637, compoundHCID 128055256-(5-Cholesten-3beta-yloxy)hexyl iodide

Product 1

HCID 13799774HCID 13799774, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranose (287 mg, 0.79 mmol) in dichloromethane (6 ml) was added cholest-5-en-3β-yl 6-iodohexyl ether (470 mg, 0.79 mmol) and triethylamine (0.11 ml, 0.79 mmol). After stirring under dry nitrogen atmosphere overnight at room temperature, the solvent was removed at reduced pressure and the residue chromatographed on silica gel eluted with 5-25% ethyl acetate in hexanes to give 6-(cholest-5-en-3β-yloxy)hexyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside (0.36 g, 55% yield), m.p. 103°-103.5° C. This product was dissolved in 1:1 (v/v) ethanol-tetrahydrofuran (10 ml) and treated with a suspension of Bio-Rad AG-1-X2 OH- ion-exchange resin (2.5-3 fold excess) in ethanol (5 ml). After stirring a room temperature for 45 minutes, the resin was filtered and washed with warm tetrahydrofuran (3×5 ml), and the combined filtrates concentrated to give 6-(5-cholesten-3β -yloxy)hexyl 1-thio-α-D-mannopyranoside (250 mg, 91% yield) as needles from warm tetrahydrofuran, m.p. (endothermic transitions) 64-64, 81-82, and 226°-227° C.

Workup

  1. customthe solvent was removed at reduced pressure
  2. customthe residue chromatographed on silica gel
  3. washeluted with 5-25% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-fcf805fbf10b41d1a4f2105cd50708ba
Source dataset
uspto-grants-1990_07
Patent number
US04942154

Reaction notes

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