Methanol → 3-O-(2,3,4-tri-O-benzyl-6-thio acetyl-alpha-D-quinovopyranosyl)-1-O-stearoyl-propane-1,3-diol

HRID 1009677Notes

Reaction equation

HRID 1009677 reaction equation
[CH2:1]([O:8][C@@H:9]1[C@@H:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@H:13]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@@H:12]([CH2:31][C:32](=[S:34])[CH3:33])[O:11][C@@H:10]1[O:35][CH2:36][CH2:37][CH2:38][OH:39])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:40](Cl)(=[O:58])[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH3:57].N1C=CC=CC=1.CO>ClCCl>[CH2:1]([O:8][C@@H:9]1[C@@H:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@H:13]([O:23][CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[C@@H:12]([CH2:31][C:32](=[S:34])[CH3:33])[O:11][C@@H:10]1[O:35][CH2:36][CH2:37][CH2:38][O:39][C:40](=[O:58])[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH3:57])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 1049PyridineHCID 8212Stearoyl chlorideHCID 866333751-O-(2,3,4-tri-O-benzyl-6-thioacetyl-alpha-D-quinovopyranosyl)-propane-1,3-diol

Product 1

HCID 866333763-O-(2,3,4-tri-O-benzyl-6-thio acetyl-alpha-D-quinovopyranosyl)-1-O-stearoyl-propane-1,3-diol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the compound (7) (21.9 g, 38.6 mmol) in anhydrous dichloromethane (200 ml), added were stearoyl chloride (15.2 g, 1.3 equivalents) and anhydrous pyridine (5 ml), and the mixture was stirred at room temperature for 2 hours. After the sufficient progress of the reaction was confirmed, methanol (5 ml) was added to stop the reaction, and the mixture was concentrated under reduced pressure. The residue was suspended in a minor amount of ethyl acetate, poured to water (200 ml), and extracted with ethyl acetate (3×100 ml). The organic layers were combined and washed with saturated saline (2×100 ml), dried with sodium sulfate, filtered, and concentrated under reduced pressure. The obtained residue was purified with silica gel chromatography (hexane-ethyl acetate, 10:1→8:1→6:1) to obtain the title compound (8) in the form of a colorless oily substance {31.3 g (37.6 mmol), 97.4%}.

Workup

  1. customthe reaction
  2. concentrationthe mixture was concentrated under reduced pressure
  3. additionpoured to water (200 ml)
  4. extractionextracted with ethyl acetate (3×100 ml)
  5. washwashed with saturated saline (2×100 ml)
  6. dry with materialdried with sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe obtained residue was purified with silica gel chromatography (hexane-ethyl acetate, 10:1→8:1→6:1)

Sources & evidence

ORD record
ord-d9ea490696ba4260ab6cb8ca818ca586
Source dataset
uspto-grants-2011_07
Patent number
US07973145B2

Reaction notes

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