HCID 86741641, compound → HCID 54345445, compound

HRID 653333Notes

Reaction equation

HRID 653333 reaction equation
C([O:4][C@@H:5]1[C@@H:32]([O:33]C(=O)C)[C@H:31]([O:37][C@@H:38]2[O:75][C@H:74]([CH2:76][O:77]C(=O)C)[C@H:49]([O:50][C@H:51]3[O:68][C@H:67]([CH2:69][O:70]C(=O)C)[C@H:62]([O:63]C(=O)C)[C@H:57]([O:58]C(=O)C)[C@H:52]3[O:53]C(=O)C)[C@H:44]([O:45]C(=O)C)[C@H:39]2[O:40]C(=O)C)[C@@H:30]([CH2:81][O:82]C(=O)C)[O:29][C@H:6]1[O:7][CH2:8][CH2:9][S:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])(=O)C>C[O-].[Na+]>[C@H:51]1([O:50][C@H:49]2[C@@H:74]([CH2:76][OH:77])[O:75][C@@H:38]([O:37][C@@H:31]3[C@@H:30]([CH2:81][OH:82])[O:29][C@@H:6]([O:7][CH2:8][CH2:9][S:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[C@H:5]([OH:4])[C@H:32]3[OH:33])[C@H:39]([OH:40])[C@H:44]2[OH:45])[O:68][C@H:67]([CH2:69][OH:70])[C@H:62]([OH:63])[C@H:57]([OH:58])[C@H:52]1[OH:53]

Participants

3

Reactant 1

HCID 86741641HCID 86741641, compound

Product 1

HCID 54345445HCID 54345445, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 10942334Sodium MethoxideSolvent

Procedure

A solution of 65 (1.0 g, 0.81 mmol) in methanolic sodium methoxide (0.003M, 100 ml) was left at room temperature for 24 h and neutralized with Duolite C26 (H+) resin. The solvent was removed and the residue was dissolved in water (300 ml) and lyophilized to give 66 (580 mg, 88%) with [α]D21 +42° (c 0.7, dimethylsulfoxide). 1H-NMR (DMSO-d6, 50°, D2O added, Me4Si) δ 4.81 (d, 1H, J=3.5 Hz, H1"), 4.27, 4.24 (2d, each 1H, J=7 and 8 Hz, H1 and H1'), 2.67, 2.52 (2t, each 2H, J=7.5 Hz, CH2 --S--CH2), 0.86 (t, 3H, J=6.5 Hz, Me). 13C-NMR (CDCl3 --CD3OD 1:5) δ 105.2, 104.1 (2d, J=162 Hz, Cl, Cl'), 102.6 (d, J=172 Hz, Cl"), 81.1, 80.0, 76.3 (3C), 74.6, (2C), 72.9, 72.5, 71.1, 70.9, 70.4, 70.3 (CH2), 62.7 (CH2), 62.0 (CH2), 61.3 (CH2), 33.2-29.7 (CH2), 23.5 (CH2), 14.4 (CH3).

Workup

  1. customThe solvent was removed
  2. dissolutionthe residue was dissolved in water (300 ml)

Sources & evidence

ORD record
ord-b3b8086317f241a8affdfce9d9200478
Source dataset
uspto-grants-1987_06
Patent number
US04675392

Reaction notes

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