S-(2,3,4,6-tetra-o-acetyl-β-D-glucopyranosyl) (Z)-2-phenylethanethiohydroximate

Base Information

Chemical Name:S-(2,3,4,6-tetra-o-acetyl-β-D-glucopyranosyl) (Z)-2-phenylethanethiohydroximate
CAS No.:156258-43-4
Molecular Formula:C₂₂H₂₇NO₁₀S
Molecular Weight:497.523
Hs Code.:

Synonyms:S-(2,3,4,6-tetra-o-acetyl-β-D-glucopyranosyl) (Z)-2-phenylethanethiohydroximate

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Chemical Property of S-(2,3,4,6-tetra-o-acetyl-β-D-glucopyranosyl) (Z)-2-phenylethanethiohydroximate

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Technology Process of S-(2,3,4,6-tetra-o-acetyl-β-D-glucopyranosyl) (Z)-2-phenylethanethiohydroximate

There total 6 articles about S-(2,3,4,6-tetra-o-acetyl-β-D-glucopyranosyl) (Z)-2-phenylethanethiohydroximate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 85.0%

: 19879-84-6
tetraacetyl thioglucose

: 1300707-63-4
N-(tert-butyldimethylsilyloxy)-2-phenylacetamide

: 156258-43-4
S-(2,3,4,6-tetra-o-acetyl-β-D-glucopyranosyl) (Z)-2-phenylethanethiohydroximate

Guidance literature:: N-(tert-butyldimethylsilyloxy)-2-phenylacetamide; With trifluoromethylsulfonic anhydride; triethylamine; In dichloromethane; at -78 - 0 ℃; for 1h; Inert atmosphere;

tetraacetyl thioglucose; In dichloromethane; at 20 ℃; for 15h; Inert atmosphere;
DOI:10.1002/ejoc.201001438

Reference yield: 83.0%

: 19879-84-6
tetraacetyl thioglucose

: (Z)-N-hydroxy-2-phenylacetimidoyl chloride

: 156258-43-4
S-(2,3,4,6-tetra-o-acetyl-β-D-glucopyranosyl) (Z)-2-phenylethanethiohydroximate

Guidance literature:: With triethylamine; In diethyl ether; dichloromethane; at 20 ℃; for 2h; stereospecific reaction; Inert atmosphere;
DOI:10.1016/j.bmc.2013.07.049

Reference yield:

: 103-80-0
phenylacetyl chloride

: 156258-43-4
S-(2,3,4,6-tetra-o-acetyl-β-D-glucopyranosyl) (Z)-2-phenylethanethiohydroximate

Guidance literature:: Multi-step reaction with 3 steps

1.1: hydroxylamine hydrochloride; potassium hydroxide / methanol / 0 - 20 °C / Inert atmosphere

2.1: 1H-imidazole / N,N-dimethyl-formamide / 16 h / 20 °C / Inert atmosphere; Cooling with ice

3.1: trifluoromethylsulfonic anhydride; triethylamine / dichloromethane / 1 h / -78 - 0 °C / Inert atmosphere

3.2: 15 h / 20 °C / Inert atmosphere

With 1H-imidazole; trifluoromethylsulfonic anhydride; hydroxylamine hydrochloride; triethylamine; potassium hydroxide; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/ejoc.201001438