Methanol → HCID 67024436, compound

HRID 215723Notes

Reaction equation

C([Si](C)(C)[O:6][C@H:7]1[C@:11]([C:14]#[CH:15])([CH2:12][OH:13])[O:10][C@@H:9]([N:16]2[CH:24]=[C:22]([CH3:23])[C:20](=[O:21])[NH:19][C:17]2=[O:18])[CH2:8]1)(C)(C)C.[CH3:27]O>>[CH2:14]([C@:11]1([CH2:12][OH:13])[O:10][C@@H:9]([N:16]2[CH:24]=[C:22]([CH3:23])[C:20](=[O:21])[NH:19][C:17]2=[O:18])[CH2:8][C@@H:7]1[OH:6])[CH:15]=[CH2:27]

Participants

Reactant 2

HCID 887Methanol

HCID 86639218HCID 86639218, compound

Product 1

HCID 67024436HCID 67024436, compound

Procedure

Physical data for 10b: mp 96-98° C.; UV (MeOH): λmax 267 nm (ε9300), λmin 235 nm (ε1700). 1H NMR (CDCl3) δ0.08 and 0.13 (6H, each as s, SiMe), 0.89 (9H, s, SiBu-t), 1.93 (3H, d, J6,CH3=0.9 Hz, Me), 2.12-2.17 (1H, m, H-2′a), 2.63 (1H, br, OH), 2.71-2.77 (1H, m, H-2′b), 2.75 (1H, s, ethynyl), 3.67 (1H, d, Jgem=11.5 Hz, H-5′a), 3.74 (1H, d, Jgem=11.5 Hz, H-5′b), 4.47 (1H, t, J2′a,3′=J2′b,3′=5.3 Hz, H-3′), 6.30 (1H, dd, J1′,2′a=4.8 Hz and J1′,2′b=6.9 Hz, H-1′), 7.80 (1H, d, J6,CH3=0.9 Hz, H-6), 9.00 (1H, brs, NH); FAB-MS m/z 381 (M++H). Anal. Calcd for C18H28N2O5Si: C, 56.82; H, 7.42; N, 7.36. Found: C, 56.57; H, 7.58; N, 7.19.

Sources & evidence

ORD record: ord-bc99517e4dbc4f7fb323ba92b1db8929
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08193165B2

Reaction notes

Loading…