HCID 86741642, compound → HCID 54300994, compound

HRID 653335Notes

Reaction equation

HRID 653335 reaction equation
C([O:4][C@@H:5]1[C@@H:13]([O:14]C(=O)C)[C@H:12]([O:18][C@@H:19]2[O:56][C@H:55]([CH2:57][O:58]C(=O)C)[C@H:30]([O:31][C@H:32]3[O:49][C@H:48]([CH2:50][O:51]C(=O)C)[C@H:43]([O:44]C(=O)C)[C@H:38]([O:39]C(=O)C)[C@H:33]3[O:34]C(=O)C)[C@H:25]([O:26]C(=O)C)[C@H:20]2[O:21]C(=O)C)[C@@H:11]([CH2:62][O:63]C(=O)C)[O:10][C@H:6]1[O:7][CH2:8][CH3:9])(=O)C>C[O-].[Na+]>[C@H:32]1([O:31][C@H:30]2[C@@H:55]([CH2:57][OH:58])[O:56][C@@H:19]([O:18][C@@H:12]3[C@@H:11]([CH2:62][OH:63])[O:10][C@@H:6]([O:7][CH2:8][CH3:9])[C@H:5]([OH:4])[C@H:13]3[OH:14])[C@H:20]([OH:21])[C@H:25]2[OH:26])[O:49][C@H:48]([CH2:50][OH:51])[C@H:43]([OH:44])[C@H:38]([OH:39])[C@H:33]1[OH:34]

Participants

3

Reactant 1

HCID 86741642HCID 86741642, compound

Product 1

HCID 54300994HCID 54300994, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 10942334Sodium MethoxideSolvent

Procedure

A solution of 67 (440 mg, 0.46 mmol) in methanolic sodium methoxide (0.005M, 40 ml) was left at room temperature for 18 h, then neutralized with Duolite C26 (H+) resin and the solvent was removed. The residue was dissolved in water and lyophilized to give 68 (245 mg, 100%) with [α]D21 +71° (c 0.5, water) 1H-NMR (DMSO-d6, 50°, D2O added, Me4Si) δ 4.81 (d, 1H, J=3.5 Hz, H1"), 4.28, 4.20 (d, each 1H, J=7 and 8 Hz, H1 and H1'), 1.14 (t, 3H, J=7 Hz, CH3 --CH2). 13C-NMR (D2O, TSP) δ 106.1, 104.5, 103.2 (Cl, l', l"), 81.5, 80.2, 78.3, 77.7, 77.3, 75.8, 75.0, 73.7, 73.6, 72.0, 71.8, 71.4, 69.1 (CH2), 63.3 (CH2), 63.2 (CH2), 62.9 (CH2), 17.1. Sugar49 and methylation50 analysis was in agreement with the proposed structure.

Workup

  1. customthe solvent was removed
  2. dissolutionThe residue was dissolved in water

Sources & evidence

ORD record
ord-568cf4bfea6140229ef8bf1f6aa03dfd
Source dataset
uspto-grants-1987_06
Patent number
US04675392

Reaction notes

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