Lithium azide → 1,4-Anhydro-5-azido-5-deoxy-2-S-[(4-methoxyphenyl)-methyl]-2-thio-L-arabinitol

HRID 54825

Reaction equation

CC1C=CC(S(O[CH2:12][C@@H:13]2[O:17][CH2:16][C@H:15]([S:18][CH2:19][C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=3)[C@H:14]2[OH:28])(=O)=O)=CC=1.[N-:29]=[N+:30]=[N-:31].[Li+]>CN(C)C=O>[N:29]([CH2:12][C@@H:13]1[O:17][CH2:16][C@H:15]([S:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[C@H:14]1[OH:28])=[N+:30]=[N-:31]

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 2.0 g of product from Example 324, 0.460 g of lithium azide and 2 ml of N,N-dimethylformamide is stirred at 70° C. for 65 hours. The reaction mixture is concentrated in vacuo. The residue is purified by chromatography (Silica gel: 30% ethyl acetate/hexane) to give 0.454 g of the desired product.

Workup

concentrationThe reaction mixture is concentrated in vacuo
customThe residue is purified by chromatography (Silica gel: 30% ethyl acetate/hexane)

Sources & evidence

ORD record: ord-5061bb5743e04cedafaf182a0c9038b8
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05623081

Linked notes

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