2,3,4,6-tetra-O-acetyl-1-S-(Z)-4-cyanobenzohydroximoyl-1-thio-β-D-glucopyranose

Base Information

• Chemical Name: 2,3,4,6-tetra-O-acetyl-1-S-(Z)-4-cyanobenzohydroximoyl-1-thio-β-D-glucopyranose
• CAS No.: 1187735-07-4
• Molecular Formula: C₂₂H₂₄N₂O₁₀S
• Molecular Weight: 508.506

Synonyms:2,3,4,6-tetra-O-acetyl-1-S-(Z)-4-cyanobenzohydroximoyl-1-thio-β-D-glucopyranose

Chemical Property of 2,3,4,6-tetra-O-acetyl-1-S-(Z)-4-cyanobenzohydroximoyl-1-thio-β-D-glucopyranose

Chemical Property:

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Technology Process of 2,3,4,6-tetra-O-acetyl-1-S-(Z)-4-cyanobenzohydroximoyl-1-thio-β-D-glucopyranose

There total 1 articles about 2,3,4,6-tetra-O-acetyl-1-S-(Z)-4-cyanobenzohydroximoyl-1-thio-β-D-glucopyranose 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: 48.0%

tetraacetyl thioglucose (19879-84-6) + 4-cyano-N-hydroxy-benzenecarboximidoyl chloride (123476-70-0) → 2,3,4,6-tetra-O-acetyl-1-S-(Z)-4-cyanobenzohydroximoyl-1-thio-β-D-glucopyranose (1187735-07-4)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃;

DOI:10.1016/j.bmc.2009.05.080

Reference yield: 86.0%

2,3,4,6-tetra-O-acetyl-1-S-(Z)-4-cyanobenzohydroximoyl-1-thio-β-D-glucopyranose (1187735-07-4) → 1-S-(Z)-4-cyanobenzohydroximoyl-1-thio-β-D-glucopyranose (1187735-13-2)

Guidance literature:

2,3,4,6-tetra-O-acetyl-1-S-(Z)-4-cyanobenzohydroximoyl-1-thio-β-D-glucopyranose; With methanol; sodium methylate; at 20 ℃; for 3h;

With Amberlite IR-120 resin (H⁺ form); In methanol; pH=5 - 6;

DOI:10.1016/j.bmc.2009.05.080

Reference yield:

2,3,4,6-tetra-O-acetyl-1-S-(Z)-4-cyanobenzohydroximoyl-1-thio-β-D-glucopyranose (1187735-07-4) → (1S)-2,3,4,6-tetra-O-acetyl-1,5-anhydro-D-glucitol-spiro[1.5]-3-(4-cyanophenyl)-1,4,2-oxathiazole (1187735-18-7) + (1R)-2,3,4,6-tetra-O-acetyl-1,5-anhydro-D-glucitol-spiro[1.5]-3-(4-cyanophenyl)-1,4,2-oxathiazole (1206831-51-7)

Guidance literature:

With N-Bromosuccinimide; In tetrachloromethane; for 0.75h; Reflux; Irradiation;

DOI:10.1016/j.bmc.2009.05.080

upstream raw materials:

tetraacetyl thioglucose

4-cyano-N-hydroxy-benzenecarboximidoyl chloride

Downstream raw materials:

1-S-(Z)-4-cyanobenzohydroximoyl-1-thio-β-D-glucopyranose

(1S)-2,3,4,6-tetra-O-acetyl-1,5-anhydro-D-glucitol-spiro[1.5]-3-(4-cyanophenyl)-1,4,2-oxathiazole

(1R)-2,3,4,6-tetra-O-acetyl-1,5-anhydro-D-glucitol-spiro[1.5]-3-(4-cyanophenyl)-1,4,2-oxathiazole

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