HCID 446373, compound → HCID 131732355, compound

HRID 1428141Notes

Reaction equation

HRID 1428141 reaction equation
[CH3:1][C@H:2]([CH2:31][CH2:32][CH2:33][C@H:34]([CH3:46])[CH2:35][CH2:36][CH2:37][C@H:38]([CH3:45])[CH2:39][CH2:40][CH2:41][CH:42]([CH3:44])[CH3:43])[CH2:3][CH2:4][O:5][C@@H:6]([CH2:9][O:10][CH2:11][CH2:12][C@H:13]([CH3:30])[CH2:14][CH2:15][CH2:16][C@H:17]([CH3:29])[CH2:18][CH2:19][CH2:20][C@H:21]([CH3:28])[CH2:22][CH2:23][CH2:24][CH:25]([CH3:27])[CH3:26])[CH2:7][OH:8].ClC(Cl)(Cl)C(=N)O[C@H:51]1[O:76][C@H:75]([CH2:77][O:78][CH2:79][C:80]2[CH:85]=[CH:84][CH:83]=[CH:82][CH:81]=2)[C@@H:66]([O:67][CH2:68][C:69]2[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=2)[C@H:57]([O:58][CH2:59][C:60]2[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=2)[C@@H:52]1[O:53][C:54](=[O:56])[CH3:55].C([Si](OS(C(F)(F)F)(=O)=O)(CC)CC)C>C(Cl)Cl>[C:54]([O:53][C@H:52]1[C@@H:57]([O:58][CH2:59][C:60]2[CH:61]=[CH:62][CH:63]=[CH:64][CH:65]=2)[C@H:66]([O:67][CH2:68][C:69]2[CH:70]=[CH:71][CH:72]=[CH:73][CH:74]=2)[C@@H:75]([CH2:77][O:78][CH2:79][C:80]2[CH:81]=[CH:82][CH:83]=[CH:84][CH:85]=2)[O:76][C@@H:51]1[O:8][CH2:7][CH:6]([O:5][CH2:4][CH2:3][C@H:2]([CH3:1])[CH2:31][CH2:32][CH2:33][C@H:34]([CH3:46])[CH2:35][CH2:36][CH2:37][C@H:38]([CH3:45])[CH2:39][CH2:40][CH2:41][CH:42]([CH3:44])[CH3:43])[CH2:9][O:10][CH2:11][CH2:12][C@H:13]([CH3:30])[CH2:14][CH2:15][CH2:16][C@H:17]([CH3:29])[CH2:18][CH2:19][CH2:20][C@H:21]([CH3:28])[CH2:22][CH2:23][CH2:24][CH:25]([CH3:26])[CH3:27])(=[O:56])[CH3:55]

Participants

5

Reactant 3

HCID 446373HCID 446373, compoundHCID 2733308Triethylsilyl trifluoromethanesulphonateHCID 11125075HCID 11125075, compound

Product 1

HCID 131732355HCID 131732355, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of (2R)-2,3-Bis[(3R,7R,11R)-3,7,11,15-tetramethylhexadecyloxy]propan-1-ol (archaeol) (720 mg; 1.1 mmol), 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl trichloroacetimidate (1.4 g; 2.2 mmol) and molecular sieves 4A° (3 g) was added CH2Cl2 (15 ml). After stirring at R.T. under an argon atmosphere for 1 h, triethylsilyltrifluoromethanesulfonate (25 μL; 0.11 mmol) was added and the stirring continued for 40 min. The reaction was quenched with diisopropylethylamine (100 μL). The whole reaction was adsorbed on silica gel and then purified by silica gel chromatography eluting with hexanes:ethyl acetate 9:1 to yield pure product as a viscous oil (0.58 g; 47%) plus some mixed fractions.

Workup

  1. waitthe stirring continued for 40 min
  2. customThe reaction was quenched with diisopropylethylamine (100 μL)
  3. customThe whole reaction
  4. custompurified by silica gel chromatography
  5. washeluting with hexanes:ethyl acetate 9:1

Sources & evidence

ORD record
ord-3df2fc295d8e43b58c1d9289221c6716
Source dataset
uspto-grants-2015_01
Patent number
US08936793B2

Reaction notes

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