Triethylamine → HCID 54085480, compound

HRID 2417856Notes

Reaction equation

HRID 2417856 reaction equation
C([O:4][C@@H:5]1[C@@H:19]([O:20]C(=O)C)[C@H:18]([O:24][C@H:25]2[O:42][C@H:41]([CH2:43][O:44]C(=O)C)[C@@H:36]([O:37]C(=O)C)[C@H:31]([O:32]C(=O)C)[C@H:26]2[O:27]C(=O)C)[C@@H:17]([CH2:48][O:49]C(=O)C)[O:16][C@H:6]1[S:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1)(=O)C.C(N(CC)CC)C>CO.CO.O>[C@H:25]1([O:24][C@@H:18]2[C@@H:17]([CH2:48][OH:49])[O:16][C@@H:6]([S:7][C:8]3[CH:9]=[CH:10][C:11]([O:14][CH3:15])=[CH:12][CH:13]=3)[C@H:5]([OH:4])[C@H:19]2[OH:20])[O:42][C@H:41]([CH2:43][OH:44])[C@@H:36]([OH:37])[C@H:31]([OH:32])[C@H:26]1[OH:27]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 13384949HCID 13384949, compound

Product 1

HCID 54085480HCID 54085480, compoundYield 81.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 22242641Methanol--water (1/1)Solvent

Procedure

A mixture comprising 2.6 g of 4-methoxyphenyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside in 25 ml of cold methanol was combined with a cold mixture of 2N triethylamine in methanol:water (6:2). This mixture was refrigerated overnight, then evaporated in vacuo to a solid which was triturated with ether, giving 1.3 g of the desired intermediate, UV 225-245 nm.

Workup

  1. customevaporated in vacuo to a solid which
  2. customwas triturated with ether

Sources & evidence

ORD record
ord-decc350a235e440cb8648c966c12a9fe
Source dataset
uspto-grants-1984_09
Patent number
US04470976

Reaction notes

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