Tert-butyl but-3-EN-1-ylcarbamate → (2S,3S,4R,5S,6R)-2-(3-(4-(4-aminobutyl)benzyl)-4-methylphenyl)-6-(methylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate

HRID 1499296Notes

Reaction equation

HRID 1499296 reaction equation
[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([S:19][CH3:20])[O:7][C@H:6]1[C:21]1[CH:26]=[CH:25][C:24]([CH3:27])=[C:23]([CH2:28][C:29]2[CH:34]=[CH:33][C:32]([CH2:35][CH2:36]CCCN)=[CH:31][CH:30]=2)[CH:22]=1)(=[O:3])[CH3:2].[CH2:41]([NH:45]C(=O)OC(C)(C)C)[CH2:42]C=C>>[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([S:19][CH3:20])[O:7][C@H:6]1[C:21]1[CH:26]=[CH:25][C:24]([CH3:27])=[C:23]([CH2:28][C:29]2[CH:34]=[CH:33][C:32]([CH2:35][CH2:36][CH2:42][CH2:41][NH2:45])=[CH:31][CH:30]=2)[CH:22]=1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 11263760Tert-butyl but-3-EN-1-ylcarbamateHCID 76070895(2S,3S,4R,5S,6R)-2-(3-(4-(5-aminopentyl)benzyl)-4-methylphenyl)-6-(methylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Product 1

HCID 90177035(2S,3S,4R,5S,6R)-2-(3-(4-(4-aminobutyl)benzyl)-4-methylphenyl)-6-(methylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Procedure

The same procedure was employed as used for the synthesis of (2S,3S,4R,5S,6R)-2-(3-(4-(5-aminopentyl)benzyl)-4-methylphenyl)-6-(methylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate (16), using tert-butyl but-3-en-1-ylcarbamate as the reagent for the Heck reaction.

Workup

  1. customfor the Heck reaction

Sources & evidence

ORD record
ord-4f9c79df34964a51932212c24ffc1eb8
Source dataset
uspto-grants-2015_12
Patent number
US09200025B2

Reaction notes

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