HCID 69228002, compound → HCID 87740904, compound

HRID 1182013Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:68]=[C:69]([O:79][CH2:80][C:81]2[CH:86]=[CH:85][CH:84]=[CH:83][CH:82]=2)[C:70]=1[O:71][CH2:72][C:73]1[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=1)[C:12]([C@@:14]1([OH:67])[C@@:30]([C:32](=[O:63])[C:33]2[CH:38]=[C:37]([O:39][CH2:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[C:36]([O:47][CH2:48][C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=3)=[C:35]([O:55][CH2:56][C:57]3[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=3)[CH:34]=2)([OH:31])[C@H:29]([OH:64])[C@@H:28]([CH2:65][OH:66])[O:27][C@H:15]1[O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[N+:24]([O-:26])=[O:25])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:87]([C:95]1[C:96]2[O:118][CH2:117][O:116][C:101](=[C:102]([C:110]3[CH:115]=[CH:114][CH:113]=[CH:112][CH:111]=3)[C:103]=1[C:104]1[CH:109]=[CH:108][CH:107]=[CH:106][CH:105]=1)[C:97]=2[C:98](O)=[O:99])[Si:88]([C:91]([CH3:94])([CH3:93])[CH3:92])([CH3:90])[CH3:89]>>[O:87]([C:95]1[C:96]2[O:118][CH2:117][O:116][C:101](=[C:102]([C:110]3[CH:111]=[CH:112][CH:113]=[CH:114][CH:115]=3)[C:103]=1[C:104]1[CH:109]=[CH:108][CH:107]=[CH:106][CH:105]=1)[C:97]=2[C:98]([C@@:29]1([OH:64])[C@@H:28]([CH:65]([C:98](=[O:99])[C:97]2[C:101]3[O:116][CH2:117][O:118][C:96]=2[C:95]([O:87][Si:88]([C:91]([CH3:93])([CH3:92])[CH3:94])([CH3:89])[CH3:90])=[C:103]([C:104]2[CH:105]=[CH:106][CH:107]=[CH:108][CH:109]=2)[C:102]=3[C:110]2[CH:115]=[CH:114][CH:113]=[CH:112][CH:111]=2)[OH:66])[O:27][C@@H:15]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[N+:24]([O-:26])=[O:25])[C@:14]([C:12](=[O:13])[C:11]2[CH:10]=[C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:70]([O:71][CH2:72][C:73]3[CH:74]=[CH:75][CH:76]=[CH:77][CH:78]=3)=[C:69]([O:79][CH2:80][C:81]3[CH:82]=[CH:83][CH:84]=[CH:85][CH:86]=3)[CH:68]=2)([OH:67])[C@@:30]1([C:32](=[O:63])[C:33]1[CH:34]=[C:35]([O:55][CH2:56][C:57]2[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=2)[C:36]([O:47][CH2:48][C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)=[C:37]([O:39][CH2:40][C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=2)[CH:38]=1)[OH:31])=[O:99])[Si:88]([C:91]([CH3:92])([CH3:93])[CH3:94])([CH3:90])[CH3:89]

Participants

Reactant 2

HCID 69228002HCID 69228002, compound

HCID 87741958HCID 87741958, compound

Product 1

HCID 87740904HCID 87740904, compoundYield 81.7%

Procedure

By use of general procedure B, 2-nitrobenzyl 2,3-bis(3,4,5-tris(benzyloxy)benzoyl)-β-D-glucopyranoside (2.10 g, 1.81 mmol) was coupled with 3-tert-butyldimethylsiloxy-4,5-diphenylmethylenedioxybenzoic acid (1.62 g, 3.62 mmol) to afford 2.99 g (80%) of 2-nitrobenzyl 4,6-bis(3-tert-butyldimethylsiloxy-4,5-diphenylmethylenedioxybenzoyl)-2,3-bis(3,4,5-tris(benzyloxy)benzoyl)-β-D-glucopyranoside as a white solid foam following flash column chromatography using 10%, and then 20%, EtOAc in hexanes as eluent. IR (CH2Cl2) 1729 cm−1; 1H NMR (CDCl3, 75 MHz) δ 8.05 (d, J=1.3 Hz, 1H), 7.98 (d, J=4 Hz, 1H), 7.70-7.15 (m, 60H), 5.84 (t, J=9.7 Hz, 1H), 5.67-5.56 (m, 2H), 5.31 (d, J=15.2 Hz, 2H), 5.13-4.89 (m, 14H), 4.64, (d, J=10.6 Hz, 1H), 4.38-4.32 (m, 1H), 4.15-4.12 (m, 1H), 0.99 (s, 9H), 0.96 (s, 9H) 0.19 (s, 6H), 0.18 (s, 6H); 13C NMR (CDCl3, 75 MHz) δ 165.6, 165.3, 164.9, 164.4, 152.5, 148.6, 146.8, 142.8, 142.0, 141.7, 139.9, 139.6, 138.6, 137.4, 136.5, 133.7, 129.2, 128.9, 128.4, 128.3, 128.1, 128.0, 127.6, 127.5, 126.2, 124.6, 124.2, 124.0, 123.5, 122.5, 119.1, 118.8, 118.2, 109.3, 109.1, 104.1, 100.1, 75.1, 75.0, 73.3, 72.8, 72.3, 71.2, 71.1, 68.9, 68.3, 62.5, 26.05, 26.04, 18.3, 18.2, −4.0; MS (+FAB) 2020 (MH+, 23). Anal. Calcd for Cl21H113NO24Si2: C, 71.92; H. 5.59; N, 0.69; Found: C, 72.16; H, 5.80: N, 0.58.

Sources & evidence

ORD record: ord-f0ec1c24e127475e8232a376d4507028
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07288273B1

Reaction notes

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