Acetic Anhydride → 2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxymannopyranose

HRID 547871노트

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HRID 547871 반응식
[C:1]([NH:4][C@H:5]1[C@@H:11]([OH:12])[C@H:10]([OH:13])[C@@H:9]([CH2:14][OH:15])[O:8][CH:6]1[OH:7])(=[O:3])[CH3:2].C(O[C:20](=[O:22])[CH3:21])(=O)C>N1C=CC=CC=1.CN(C1C=CN=CC=1)C>[C:1]([O:7][CH:6]1[O:8][C@H:9]([CH2:14][O:15][C:20](=[O:22])[CH3:21])[C@@H:10]([O:13][C:9](=[O:8])[CH3:10])[C@H:11]([O:12][C:6](=[O:7])[CH3:5])[C@@H:5]1[NH:4][C:1](=[O:3])[CH3:2])(=[O:3])[CH3:2]

참가 물질

5

반응물 2

HCID 7918Acetic AnhydrideHCID 439281N-Acetyl-D-Mannosamine

생성물 1

HCID 1271322-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxymannopyranose수율 187.1%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 1049Pyridine용매

실험 절차

A solution of N-acetylmannosamine (100 mg, 0.420 mmol) in pyridine (5 mL) was stirred at 0° C. To this solution was added acetic anhydride (5.0 mL, 53 mmol) and a catalytic amount of DMAP. The mixture was stirred overnight and allowed to warm to rt. Concentration and co-evaporation with toluene (6×10 mL) afforded the crude product which was purified via silica gel chromatography eluting with a gradient of 1:4 to 1:1 EtOAc/hexanes, yielding 153 mg (94%) of a viscous oil. IR (thin film): 3368: 2965, 2255, 1750, 1665, 1536 cm−1. 1H NMR (500 MHz, CDCl3): δ2.05 (app s, 6H), 2.051 (app s, 6H), 2.08 (app s, 9H), 2.08 (s, 3H), 2.085 (s, 3H), 2.09 (s, 3H), 3.79 (ddd, 1,H, J=2.5, 5.3, 9.6), 4.02-4.05 (m, 2H), 4.08 (dd, 1H, J=2.4, 12.4), 4.27 (dd, 1H J=3.8, 5.5), 4.29 (dd, 1H, J=3.2, 5.5), 4.62 (ddd, 1H, J=1.8, 4.5, 9.2), 4.76 (ddd, 1H, J=1.7, 4.0, 9.1), 5.04 (dd, 1H, J=4.0, 9.9), 5.11 (app t, in, J=9.7), 5.15 (app t, 1H, J =10.0), 5.32 (dd, 1H, J=4.5, 10.2), 5.84 (d, 1H, J=1.7), 5.92 (d, 1H, J=9.1), 6.00 (d, 1H, J=1.7), 6.01 (d, 1H, J=9.1). 13C NMR (125 MHz, CDCl3) : δ20.5, 20.6, 20.7 20.8, 23.1, 23.3, 49.3, 49.5, 50.7, 61.9, 62.1, 65.3, 65.5, 68.8, 70.1, 71.3, 73.4, 76.7, 77.0, 77.2, 90.6, 91.7, 169.6, 169.7, 169.9, 170.0, 170.2, 170.5. HRMS (FAB) m/z 412.1227 (MNa+C16H23NNaO10 requires 412.1220).

후처리

  1. concentrationConcentration and co-evaporation with toluene (6×10 mL)
  2. customafforded the crude product which
  3. customwas purified via silica gel chromatography
  4. washeluting with a gradient of 1:4 to 1:1 EtOAc/hexanes

출처 및 근거

ORD 기록
ord-199e900333654121b3b9070c9f6911bb
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07939626B2

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