Triethyl orthoacetate → HCID 24770811, compound

HRID 600148Notes

Reaction equation

HRID 600148 reaction equation
[CH2:1]([O:8][C@H:9]1[C@H:23]([CH3:24])[O:22][C@@H:12]([O:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[C@H:11]([OH:25])[C@@H:10]1[OH:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:27]([O:29]C(OCC)(OCC)C)[CH3:28]>CN(C=O)C>[C:27]([O:25][C@@H:11]1[C@H:10]([OH:26])[C@@H:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C@H:23]([CH3:24])[O:22][C@H:12]1[O:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)(=[O:29])[CH3:28]

Participants

4

Reactant 2

HCID 66221Triethyl orthoacetateHCID 16658453HCID 16658453, compound

Product 1

HCID 24770811HCID 24770811, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

4-Methoxyphenyl 4-O-benzyl-α-L-rhamnopyranoside (4.06 g, 11.28 mmol) and 1,1,1-triethoxyethane (2.20 g, 2.47 mL, 13.53 mmol) are dissolved in 75 mL of DMF and stirred for 50 min at 50° C. DMF was removed in vacuo. The residue was dissolved in AcOH/H2O (4:1, v/v) and stirred for 10 min at room temperature. The acetic acid is removed in vacuo and the crude product was purified by column chromatography (3:1 hexane/EtOAc) yielding 4.51 g (98%, 2 steps) of 12 as a colorless oil: [α]D: −69.4 (c=1.25, CHCl3). IR (thin film, CHCl3): 3005, 2933, 1739, 1503, 1374, 1126, 1041 cm−1. 1H NMR (CDCl3, 300 MHz) δ 1.34 (d, J=6.0 Hz, 3H), 2.19 (s, 3H), 2.41 (b, 1H), 3.44 (t, J=9.3 Hz, 1H), 3.76 (s, 3H), 3.92 (m, 1H), 4.31 (d, J=9.0 Hz, 2H), 4.74 (d, J=12.6 Hz, 2H), 4.87 (d, J=12.6 Hz, 2H), 5.29 (m, 1H), 5.36 (s, 1H), 6.82 (d, J=9.0 Hz, 2H), 6.96 (d, J=9.0 Hz, 2H), 7.33 (m, 5H). 13C NMR (CDCl3, 75 MHz) 18.1, 21.2, 55.7, 68.1, 70.0, 72.6, 75.3, 81.6, 96.3, 114.5, 117.6, 127.8, 127.8, 128.4, 138.0, 149.9, 154.9, 170.6. MALDI-HRMS: m/z [M+Na]+ calcd 425.1571, obsd 425.1565.

Workup

  1. customDMF was removed in vacuo
  2. dissolutionThe residue was dissolved in AcOH/H2O (4:1
  3. stirringv/v) and stirred for 10 min at room temperature
  4. customThe acetic acid is removed in vacuo
  5. customthe crude product was purified by column chromatography (3:1 hexane/EtOAc)

Sources & evidence

ORD record
ord-cb6cf2d133b14b7a83615996eb1d2430
Source dataset
uspto-grants-2011_03
Patent number
US07901687B2

Reaction notes

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