2,2,2-Trifluoroethanol → HCID 59557686, compound

HRID 1175309Notes

Reaction equation

HRID 1175309 reaction equation
[Cl:1][C:2]1[C:3]([CH2:49][C:50]2[CH:55]=[CH:54][C:53]([CH2:56][CH3:57])=[CH:52][CH:51]=2)=[CH:4][C:5]([C@H:10]2[C@H:15]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C@@H:14]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C@H:13]([O:32][CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C@@H:12]([CH2:40][O:41][CH2:42][C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[O:11]2)=[C:6]([CH2:8][OH:9])[CH:7]=1.C1CCN(C(N=NC(N2CCCCC2)=O)=O)CC1.P(CCCC)(CCCC)CCCC.[C:89]([CH2:93]O)([F:92])([F:91])[F:90]>C1(C)C=CC=CC=1>[CH2:33]([O:32][C@H:13]1[C@H:14]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C@@H:15]([O:16][CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C@H:10]([C:5]2[CH:4]=[C:3]([CH2:49][C:50]3[CH:51]=[CH:52][C:53]([CH2:56][CH3:57])=[CH:54][CH:55]=3)[C:2]([Cl:1])=[CH:7][C:6]=2[CH2:8][O:9][CH2:93][C:89]([F:92])([F:91])[F:90])[O:11][C@@H:12]1[CH2:40][O:41][CH2:42][C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

6

Reactant 4

HCID 64092,2,2-TrifluoroethanolHCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 59557721HCID 59557721, compound

Product 1

HCID 59557686HCID 59557686, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of (5-chloro-4-(4-ethylbenzyl)-2-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)phenyl)methanol (0.783 g, 1 mmol) (V-1) in toluene (2 mL) was added ADDP (2 mmol) at room temperature. The mixture was stirred for 10 min and then Bu3P (2 mmol) was added. After stirring for 1 h, CF3CH2OH (1.0 g, 10 mmol) was added. The mixture was stirred overnight. After removal of volatiles under reduced pressure, the residue was purified by preparative LC-MS to obtain (2R,3R,4R,5S,6S)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-6-(4-chloro-5-(4-ethylbenzyl)-2-((2,2,2-trifluoroethoxy)methyl)phenyl)tetrahydro-2H-pyran (intermediate V-2).

Workup

  1. stirringAfter stirring for 1 h
  2. stirringThe mixture was stirred overnight
  3. customAfter removal of volatiles under reduced pressure
  4. customthe residue was purified by preparative LC-MS

Sources & evidence

ORD record
ord-6ac1d476acc245dbbcde5bac522d76b8
Source dataset
uspto-grants-2010_11
Patent number
US07838498B2

Reaction notes

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