2-phenyl-N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)hydrazidecarbothioamide

Base Information

• Chemical Name: 2-phenyl-N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)hydrazidecarbothioamide
• CAS No.: 69435-07-0
• Molecular Formula: C₂₁H₂₇N₃O₉S
• Molecular Weight: 497.526

Synonyms:2-phenyl-N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)hydrazidecarbothioamide

Chemical Property of 2-phenyl-N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)hydrazidecarbothioamide

Chemical Property:

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Technology Process of 2-phenyl-N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)hydrazidecarbothioamide

There total 2 articles about 2-phenyl-N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)hydrazidecarbothioamide 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: 90.0%

2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiocyanate (14152-97-7) + phenylhydrazine (100-63-0) → 2-phenyl-N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)hydrazidecarbothioamide (69435-07-0)

Guidance literature:

In dichloromethane; at 20 ℃; for 2h;

DOI:10.1016/j.bmcl.2008.11.070

Reference yield:

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (6919-96-6) → 2-phenyl-N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)hydrazidecarbothioamide (69435-07-0)

Guidance literature:

Multi-step reaction with 2 steps

2: benzene / Heating

In benzene;

Reference yield: 98.5%

Ethyl isothiocyanate (542-85-8) + 2-phenyl-N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)hydrazidecarbothioamide (69435-07-0) → Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[5-[(E)-ethylimino]-4-phenyl-[1,3,4]thiadiazolidin-(2E)-ylideneamino]-tetrahydro-pyran-3-yl ester

Guidance literature:

In benzene; for 4h; Heating;

upstream raw materials:

2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiocyanate

phenylhydrazine

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

Downstream raw materials:

2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)amino-4-phenyl-1,3,4-thiadiazol-5-one

Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[4-oxo-2-(phenyl-hydrazono)-thiazolidin-3-yl]-tetrahydro-pyran-3-yl ester

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