Triethylamine → HCID 86613970, compound

HRID 254405Notes

Reaction equation

HRID 254405 reaction equation
ClC(Cl)(Cl)C(=N)O[C@H:5]1[O:32][C@H:31]([CH2:33][O:34][C:35](=[O:42])[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C@@H:21]([O:22][C:23](=[O:30])[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C@H:16]([O:17][CH2:18][CH:19]=[CH2:20])[C@@H:6]1[O:7][C:8](=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH2:46]([O:53][C@H:54]1[C@H:67]([O:68][CH2:69][C:70]2[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=2)[C@@H:66]([CH2:76][O:77][CH2:78][C:79]2[CH:84]=[CH:83][CH:82]=[CH:81][CH:80]=2)[O:65][C@H:56]([O:57][CH2:58][C:59]2[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=2)[C@H:55]1[OH:85])[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1.[Si](OS(C(F)(F)F)(=O)=O)(C)(C)C.CCN(CC)CC>ClCCCl>[CH2:18]([O:17][C@H:16]1[C@H:21]([O:22][C:23](=[O:30])[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C@@H:31]([CH2:33][O:34][C:35](=[O:42])[C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[O:32][C@H:5]([O:85][C@H:55]2[C@@H:54]([O:53][CH2:46][C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)[C@H:67]([O:68][CH2:69][C:70]3[CH:71]=[CH:72][CH:73]=[CH:74][CH:75]=3)[C@@H:66]([CH2:76][O:77][CH2:78][C:79]3[CH:80]=[CH:81][CH:82]=[CH:83][CH:84]=3)[O:65][C@@H:56]2[O:57][CH2:58][C:59]2[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=2)[C@H:6]1[O:7][C:8](=[O:15])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[CH:19]=[CH2:20]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 65367Trimethylsilyl triflateHCID 10864493HCID 10864493, compoundHCID 11193229HCID 11193229, compound

Product 1

HCID 86613970HCID 86613970, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 3-O-allyl-2,4,6-tri-O-benzoyl-α-D-mannopyranosyl trichloroacetimidate [26] (902 mg, 1.21 mmol) and benzyl 3,4,6-tri-O-benzyl-α-D-mannopyranoside [27] (723 mg, 1.34 mmol) in 1,2-DCE (10 mL), was stirred in the presence of mol. sieves (1.0 g of 3 Å powder) under an atmosphere of argon (30 min). The mixture was cooled (0° C.) with continued stirring (10 min) prior to the addition of TMSOTf (219 μL, 1.21 mmol). After some time (10 min), Et3N (100 μL) was introduced and the mixture was filtered. The solvent was evaporated and the residue subjected to FC (10-50% EtOAc/hexane) to yield the tribenzoate (24) as, a colourless oil (1.14 g, 84%). 1H NMR (CDCl3) δ 3.67-3.81, 3.88-3.95, 4.06-4.15, 4.30-4.35 (4 m, 12H; H-2I,-3I,-4I,-5I,-6aI,-6bI,-3II,-5II,-6aII,-6bII, OCH2), 4.94-4.70 (m, 7H; CH2Ph), 4.84 (d, 1H, JA,B 10.8 Hz; A of AB quartet), 4.93-4.96, 5.04-5.09 (2 m, 2H; ═CH2), 5.02 (d, 1H, J1,2 1.9 Hz; H-1I), 5.24 (d, 1H; J1,2 1.9 Ha; H-1II), 5.59-5.69 (m, 1H; ═CH), 5.72 (dd, 1H, J2,3 3.1 Hz; H-2II), 5.75 (dd, 1H, J3,4 9.8, J4,5 9.9 Hz; H-4II), 7.09-7.58, 7.97-8.06 (2 m, 35H; Ar). 13C NMR (CDCl3) δ 61.50, 63.49 (2 C; C-6I,-6II), 68.63, 69.17, 69.31, 69.46, 69.64, 71.08, 72.04, 72.64, 73.60, 74.73, 75.30, 75.38 (13 C; C-3I,-4I,-5I,-2II,-3II,-4II,-5II, OCH2, CH2Ph), 79.97 (C-2I), 98.52, 99.60 (C-1I,-1II), 117.67 (═CH2), 127.70-138.43 (43 C; ═CH, Ar), 165.61, 165.69, 166.42 (3 C; C═O).

Workup

  1. customunder an atmosphere of argon (30 min)
  2. stirringwith continued stirring (10 min)
  3. filtrationthe mixture was filtered
  4. customThe solvent was evaporated

Sources & evidence

ORD record
ord-ce6c215d65d44cacb91b21f13fb31ecb
Source dataset
uspto-grants-2011_01
Patent number
US07875592B2

Reaction notes

Loading…