(1R,2S,3R,4R,5R)-2-Amino-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)cyclohexanol → HCID 71258191, compound

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Reaction Steps

The product of step 1 was an enantiomeric isomer of (1R,2S,3R,4R,5R)-2-amino-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)cyclohexanol described above in Intermediate Example 3, Step 3. It was prepared via a synthetic sequence substantially identical to that described above for Intermediate Example 3 Steps 1-3, starting from the enantiomeric (1R,2R,3S,4S,5S)-2-amino-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)cyclohexanol. The purification conditions for each step reaction were also the same as described, (1S,2R,3S,4S,5S)-2-Amino-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)cyclohexanol was obtained as a white solid with overall yield 58% employing procedures substantially as described for the Intermediate Example 3. 1H NMR (400 MHz, CDCl3) δ 7.37-7.25 (m, 15H), 4.98 (d, J=11.3 Hz, 1H), 4.84 (d, J=10.8 Hz, 1H), 4.69 (d, J=11.3 Hz, 1H), 4.56 (d, J=10.8 Hz, 1H), 4.47 (s, 2H), 3.64 (dd, J=4.9, 8.9 Hz, 1H), 3.54-3.48 (m, 2H), 3.30-3.26 (m, 1H), 3.16 (t, J=9.4 Hz, 1H), 2.52-2.50 (m, 1H), 2.08-2.03 (m, 1H), 1.76-1.72 (m, 1H), 1.58-1.52 (m, 1H).

Provenance & Evidence