Triethylamine → HCID 86613972, compound

HRID 1920709Notes

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.[C:46]([O:54][C@H:55]1[C@@H:60]([OH:61])[C@H:59]([O:62][C:63](=[O:70])[C:64]2[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=2)[C@@H:58]([CH2:71][O:72][C:73](=[O:80])[C:74]2[CH:79]=[CH:78][CH:77]=[CH:76][CH:75]=2)[O:57][C@@H:56]1[O:81][C@H:82]1[C@@H:95]([O:96][CH2:97][C:98]2[CH:103]=[CH:102][CH:101]=[CH:100][CH:99]=2)[C@H:94]([O:104][CH2:105][C:106]2[CH:111]=[CH:110][CH:109]=[CH:108][CH:107]=2)[C@@H:93]([CH2:112][O:113][CH2:114][C:115]2[CH:120]=[CH:119][CH:118]=[CH:117][CH:116]=2)[O:92][C@@H:83]1[O:84][CH2:85][C:86]1[CH:91]=[CH:90][CH:89]=[CH:88][CH:87]=1)(=[O:53])[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:61][C@H:60]2[C@H:59]([O:62][C:63](=[O:70])[C:64]3[CH:65]=[CH:66][CH:67]=[CH:68][CH:69]=3)[C@@H:58]([CH2:71][O:72][C:73](=[O:80])[C:74]3[CH:75]=[CH:76][CH:77]=[CH:78][CH:79]=3)[O:57][C@H:56]([O:81][C@H:82]3[C@@H:95]([O:96][CH2:97][C:98]4[CH:99]=[CH:100][CH:101]=[CH:102][CH:103]=4)[C@H:94]([O:104][CH2:105][C:106]4[CH:107]=[CH:108][CH:109]=[CH:110][CH:111]=4)[C@@H:93]([CH2:112][O:113][CH2:114][C:115]4[CH:116]=[CH:117][CH:118]=[CH:119][CH:120]=4)[O:92][C@@H:83]3[O:84][CH2:85][C:86]3[CH:91]=[CH:90][CH:89]=[CH:88][CH:87]=3)[C@H:55]2[O:54][C:46](=[O:53])[C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=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

Conditions

Temperature: 0 °C

Procedure

A mixture of 3-O-allyl-2,4,6-tri-O-benzoyl-α-D-mannopyranosyl trichloroacetimidate (742 mg, 1.01 mmol) and the alcohol (25) (908 mg, 0.84 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 (181 μL, 1.01 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 hexabenzoate (26) as, a colourless oil (1.26 g, 90%). 1H NMR (CDCl3) δ 3.51-3.56, 3.66-4.06, 4.23-4.27, 4.30-42, 4.47-4.72, 4.78-4.86 (6 m, 26 H; H-2I,-3I,-4I,-5I,-6aI,-6bI,-3II,-5II,-6aI,-6bII,-3III,-5III,-6aIII,-6bIII, OCH2, ═CH2, CH2Ph), 5.04 (d, 1 H, J1,2 1.7 Hz; H-1I), 5.15 (dd, 1 H, J1,2 1.8, J2,3 2.7 Hz; H-2II), 5.26 (d, 1 H; H-1II), 5.28 (d, 1 H, J1,2 1.7 Hz; H-1III), 5.33-5.43 (m, 1 H; ═CH), 5.77-5.82 (m, 2 H; H-4II,-2III), 5.92 (dd, 1 H, J3,4 9.5, J4,5 9.8 Hz; H-4III), 7.00-7.61, 7.80-8.19 (2 m, 50 H; Ar).

Workup

customunder an atmosphere of argon (30 min)
filtrationthe mixture was filtered
customThe solvent was evaporated

Sources & evidence

ORD record: ord-d4a35e617d80424ab736691d193d6eaf
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08173606B2

Reaction notes

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