HCID 23396150, compound → HCID 23396147, compound

HRID 967347Notes

Reaction equation

HRID 967347 reaction equation
[N:1]([C@@H:4]1[C@@H:11]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[C@H:10]([O:22][C:23]([C:25]2[C:26]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[CH:27][CH:28]=[CH:29][CH:30]=2)=[O:24])[C@@H:9]([CH2:37][O:38][Si:39]([C:52]([CH3:55])([CH3:54])[CH3:53])([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[O:8][C@H:5]1[S:6][CH3:7])=[N+]=[N-]>C(S)CCS>[NH2:1][C@@H:4]1[C@@H:11]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[C@H:10]([O:22][C:23]([C:25]2[C:26]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[CH:27][CH:28]=[CH:29][CH:30]=2)=[O:24])[C@@H:9]([CH2:37][O:38][Si:39]([C:52]([CH3:55])([CH3:54])[CH3:53])([C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=2)[C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)[O:8][C@H:5]1[S:6][CH3:7]

Participants

3

Reactant 1

HCID 23396150HCID 23396150, compound

Product 1

HCID 23396147HCID 23396147, compoundYield 91.5%

Reagents, catalysts & solvents 1

HCID 80131,3-PropanedithiolSolvent

Procedure

A mixture of methyl 2-azido-4-O-biphenylcarbonyl-6-O-tert-butyldiphenylsilyl-2-deoxy-3-O-(4-methoxybenzyl)-1-thio-β-D-glucopyranoside (11) (150 mg, 0.19 mmol) and TEA (3 drops) in 1,3-propanedithiol (1 mL) was stirred at room temperature overnight. The reaction mixture was chromatographed using EtOAc—hexane 15:85 then EtOAc—hexane 1:1 solvent systems as mobile phases to give methyl 2-amino-4-O-biphenylcarbonyl-6-O-tert-butyldiphenylsilyl-2-deoxy-3-O-(4-methoxybenzyl)-1-thio-β-D-glucopyranoside (42) (130 mg, 91%).

Workup

  1. customThe reaction mixture was chromatographed

Sources & evidence

ORD record
ord-f042f2ece25242ce994079a97b0b4330
Source dataset
uspto-grants-2005_10
Patent number
US06953850B1

Reaction notes

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