HCID 86619126, compound → HCID 86619125, compound

HRID 1182011Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:122]=[C:123]([O:133][CH2:134][C:135]2[CH:140]=[CH:139][CH:138]=[CH:137][CH:136]=2)[C:124]=1[O:125][CH2:126][C:127]1[CH:132]=[CH:131][CH:130]=[CH:129][CH:128]=1)[C:12]([C@@:14]1([OH:121])[C@@:20]([C:22](=[O:53])[C:23]2[CH:28]=[C:27]([O:29][CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:26]([O:37][CH2:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)=[C:25]([O:45][CH2:46][C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)[CH:24]=2)([OH:21])[C@:19]([C:55](=[O:86])[C:56]2[CH:61]=[C:60]([O:62][CH2:63][C:64]3[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=3)[C:59]([O:70][CH2:71][C:72]3[CH:77]=[CH:76][CH:75]=[CH:74][CH:73]=3)=[C:58]([O:78][CH2:79][C:80]3[CH:85]=[CH:84][CH:83]=[CH:82][CH:81]=3)[CH:57]=2)([OH:54])[C@@H:18]([CH:87]([C:89](=[O:120])[C:90]2[CH:95]=[C:94]([O:96][CH2:97][C:98]3[CH:103]=[CH:102][CH:101]=[CH:100][CH:99]=3)[C:93]([O:104][CH2:105][C:106]3[CH:111]=[CH:110][CH:109]=[CH:108][CH:107]=3)=[C:92]([O:112][CH2:113][C:114]3[CH:119]=[CH:118][CH:117]=[CH:116][CH:115]=3)[CH:91]=2)[OH:88])[O:17][CH:15]1[OH:16])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C1COCC1.CO>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:122]=[C:123]([O:133][CH2:134][C:135]2[CH:140]=[CH:139][CH:138]=[CH:137][CH:136]=2)[C:124]=1[O:125][CH2:126][C:127]1[CH:132]=[CH:131][CH:130]=[CH:129][CH:128]=1)[C:12]([C@@:14]1([OH:121])[C@@:20]([C:22](=[O:53])[C:23]2[CH:28]=[C:27]([O:29][CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:26]([O:37][CH2:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)=[C:25]([O:45][CH2:46][C:47]3[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=3)[CH:24]=2)([OH:21])[C@:19]([C:55](=[O:86])[C:56]2[CH:61]=[C:60]([O:62][CH2:63][C:64]3[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=3)[C:59]([O:70][CH2:71][C:72]3[CH:77]=[CH:76][CH:75]=[CH:74][CH:73]=3)=[C:58]([O:78][CH2:79][C:80]3[CH:85]=[CH:84][CH:83]=[CH:82][CH:81]=3)[CH:57]=2)([OH:54])[C@@H:18]([CH:87]([C:89](=[O:120])[C:90]2[CH:91]=[C:92]([O:112][CH2:113][C:114]3[CH:115]=[CH:116][CH:117]=[CH:118][CH:119]=3)[C:93]([O:104][CH2:105][C:106]3[CH:107]=[CH:108][CH:109]=[CH:110][CH:111]=3)=[C:94]([O:96][CH2:97][C:98]3[CH:99]=[CH:100][CH:101]=[CH:102][CH:103]=3)[CH:95]=2)[OH:88])[O:17][C@@H:15]1[OH:16])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

1,2,3,4,6-Pentakis(3,4,5-tris(benzyloxy)benzoyl)-β-D-glucopyranoside (7.0 g, 3.1 mmol) was dissolved in a mixture of 200 mL of dry THF and 100 mL of dry MeOH and cooled to 0° C. Ammonia gas was bubbled through the solution for 10 min. The reaction was stirred at 0° C. for 30 min and then allowed to warm to rt and stirred for a further period of 2.5 h. Removal of the solvents followed by flash column chromatography eluting with 10%, 25% and then 50%, EtOAc in hexanes furnished 4.16 g (73%) of 2,3,4,6-tetrakis(3,4,5-tris(benzyloxy)benzoyl)-D-glucopyranose as a white solid froth (mixture of α,β anomers). A portion of this product (30 mg) was further purified by preparative TLC using 10% EtOAc in benzene. IR (CH2Cl2) 3483, 1725 cm−1; 1H NMR (CDCl3, 300 MHz) δ 7.42-6.64 (m, 68H), 6.23, (t, J=9.9 Hz, 1H), 5.79 (d, J=3.7 Hz, 1H), 5.70 (t, J=9.9 Hz, 1H), 5.75-4.65 (m, 27H), 4.29 (dd, J=4.3 Hz, 12.1 Hz, 1H), 3.40 (bs, 1H); 13C NMR (CDCl3, 90 MHz) δ 166.7, 165.7, 165.4, 165.1, 152.54, 152.50, 152.4, 143.1, 142.9, 142.8, 142.7, 142.6, 137.4, 137.35, 137.3, 136.6, 136.45, 136.4, 136.33, 136.3, 128.5, 128.4, 128.33, 128.2, 128.1, 128.07, 128.05, 128.0, 127.94, 127.9, 127.86, 127.8, 127.78, 127.56, 127.51, 127.4, 127.3, 124.6, 124.1, 123.9, 109.4, 109.3, 109.1, 90.4, 75.1, 75.0, 72.8, 71.2, 71.1, 70.9, 70.0, 67.6, 63.1; MS (+FAB) 1869 (MH+, 0.5). Anal. Calcd for C118H100O22 C, 75.80; H, 5.35; Found: C, 76.13: H, 5.45.

Workup

customAmmonia gas was bubbled through the solution for 10 min
temperatureto warm to rt
stirringstirred for a further period of 2.5 h
customRemoval of the solvents
washeluting with 10%, 25%
custom50%, EtOAc in hexanes furnished
customA portion of this product (30 mg) was further purified by preparative TLC

Sources & evidence

ORD record: ord-db6e3a58ea6e40cba98455c76d2c6b31
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07288273B1

Reaction notes

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