Phosphate → HCID 88444072, compound

HRID 1492464Notes

Reaction equation

HRID 1492464 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[Si:6]([O:23][CH2:24][C@@H:25]1[C@@H:29]([CH2:30][O:31][Si:32]([C:45]([CH3:48])([CH3:47])[CH3:46])([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:28][CH2:27][C@@H:26]1[OH:49])([C:19]([CH3:22])([CH3:21])[CH3:20])([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(N(CC)CC)C.P([O-])([O-])([O-])=O>C(Cl)Cl>[CH3:1][S:2]([O:49][C@H:26]1[CH2:27][CH2:28][C@H:29]([CH2:30][O:31][Si:32]([C:45]([CH3:48])([CH3:47])[CH3:46])([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C@H:25]1[CH2:24][O:23][Si:6]([C:19]([CH3:20])([CH3:21])[CH3:22])([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 1061PhosphateHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 57233113HCID 57233113, compound

Product 1

HCID 88444072HCID 88444072, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

At 0° C., methanesulfonyl chloride (0.20 ml, 2.6 mmoles) was added to a solution of (1S, 2S, 3S)-2,3-bis-(t-butyldiphenylsilyloxymethyl)-1-cyclopentanol (1.08 g, 1.73 mmoles) and triethylamine (0.44 ml, 3.2 mmoles) in methylene chloride (9 ml). After stirring the mixture at 0° C. for 15 minutes, 0.2M phosphate buffer (pH 7.0) was added to the reaction mixture and the mixture was subjected to extraction with ethyl ether. The ether extract solution was dried on anhydrous sodium sulfate and then the solvent was distilled off. The residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:9, v/v) to obtain (1S,2S,3S)-2,3-bis-(t-butyldiphenylsilyloxymethyl)-1-cyclopentyl methanesulfonate (1.169 g, Yield 96%).

Workup

  1. extractionthe mixture was subjected to extraction with ethyl ether
  2. extractionThe ether extract solution
  3. dry with materialwas dried on anhydrous sodium sulfate
  4. distillationthe solvent was distilled off
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:9, v/v)

Sources & evidence

ORD record
ord-2b5d3d2f9e404fbc9d652bebb51c0a28
Source dataset
uspto-grants-1994_12
Patent number
US05374625

Reaction notes

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