Triethylamine → HCID 86613972, compound

HRID 254407Notes

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, 26H; H-2I,-3I,-4I,-5I,-6aI,-6bI,-3II,-5II,-6aII,-6bII,-3III,-5III,-6aIII,-6bIII, OCH2, ═CH2, CH2Ph), 5.04 (d, 1H, J1,2 1.7 Hz; H-1I), 5.15 (dd, 1H, J1,2 1.8, J2,3 2.7 Hz; H-2II), 5.26 (d, 1H; H-1II), 5.28 (d, 1H, J1,2 1.7 Hz; H-1III), 5.33-5.43 (m, 1H; ═CH), 5.77-5.82 (m, 2H; H-4II,-2III), 5.92 (dd, 1H, J3,4 9.5, J4,5 9.8 Hz; H-4III), 7.00-7.61, 7.80-8.19 (2 m, 50H; Ar).

Workup

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

Sources & evidence

ORD record: ord-bd9fe4978b9b4c1295cf5d8750800eb8
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07875592B2

Reaction notes

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