Sodium Methoxide → HCID 86658291, compound

HRID 74855Notes

Reaction equation

HRID 74855 reaction equation
C([O:9][C@@H:10]1[C@@H:15]([O:16]C(=O)C2C=CC=CC=2)[C@H:14]([O:25]C(=O)C2C=CC=CC=2)[C@@H:13]([CH2:34][O:35]C(=O)C2C=CC=CC=2)[O:12][C@@H:11]1[O:44][C@@H:45]1[C@@H:50]([CH2:51][O:52]C(=O)C2C=CC=CC=2)[O:49][C@H:48]([O:61][C@@H:62]2[C@@H:67]([CH2:68][O:69]C(=O)C3C=CC=CC=3)[O:66][C@H:65]([O:78][C@@H:79]3[C@@H:108]([CH2:109][O:110]C(=O)C4C=CC=CC=4)[O:107][C@@H:82]([O:83][CH2:84][CH2:85][CH2:86][NH:87][C:88](=[O:106])[CH2:89][CH2:90][CH2:91][CH2:92][CH2:93][CH2:94][CH2:95][CH2:96][CH2:97][CH2:98][CH2:99][CH2:100][CH2:101][CH2:102][CH2:103][CH2:104][CH3:105])[C@H:81]([O:119]C(=O)C4C=CC=CC=4)[C@H:80]3[O:128]C(=O)C3C=CC=CC=3)[C@H:64]([O:137]C(=O)C3C=CC=CC=3)[C@H:63]2[O:146]C(=O)C2C=CC=CC=2)[C@H:47]([O:155]C(=O)C2C=CC=CC=2)[C@H:46]1[O:164]C(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C[O-].[Na+]>CO.C1COCC1>[C@H:11]1([O:44][C@@H:45]2[C@@H:50]([CH2:51][OH:52])[O:49][C@H:48]([O:61][C@@H:62]3[C@@H:67]([CH2:68][OH:69])[O:66][C@H:65]([O:78][C@@H:79]4[C@@H:108]([CH2:109][OH:110])[O:107][C@@H:82]([O:83][CH2:84][CH2:85][CH2:86][NH:87][C:88](=[O:106])[CH2:89][CH2:90][CH2:91][CH2:92][CH2:93][CH2:94][CH2:95][CH2:96][CH2:97][CH2:98][CH2:99][CH2:100][CH2:101][CH2:102][CH2:103][CH2:104][CH3:105])[C@H:81]([OH:119])[C@H:80]4[OH:128])[C@H:64]([OH:137])[C@H:63]3[OH:146])[C@H:47]([OH:155])[C@H:46]2[OH:164])[O:12][C@H:13]([CH2:34][OH:35])[C@@H:14]([OH:25])[C@H:15]([OH:16])[C@H:10]1[OH:9]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 866582923-Stearamidopropyl 2,3,4,6-tetra-O-benzoyl-alpha-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzoyl-alpha-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzoyl-alpha-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzoyl-beta-D-glucopyranoside

Product 1

HCID 86658291HCID 86658291, compoundYield 99.7%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Glycoside 126 (377 mg, 161 μmol) was dissolved in MeOH/THF 1:1 (10 mL). NaOMe (60 μL of an 11M solution) was added and the solution was stirred at room temperature for 24 hrs. The mixture was neutralized with acidic resin and the solution filtered before the solvent was evaporated to yield the white solid product which was triturated with EtOAc and the solvent decanted (×3). The solid was dried under vacuum to yield 159 mg of the white solid product (quantitative) which was reacted on without further purification or characterisation.

Workup

  1. filtrationthe solution filtered before the solvent
  2. customwas evaporated
  3. customto yield the white solid product which
  4. customwas triturated with EtOAc
  5. customthe solvent decanted (×3)
  6. customThe solid was dried under vacuum

Sources & evidence

ORD record
ord-da7c75efe12d4bef997b557cd751a63f
Source dataset
uspto-grants-2014_09
Patent number
US08828952B2

Reaction notes

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