3-O-benzyl-4-O-(4-fluorophenylthionocarbonyl)-1,2-O-(1-methoxyethylidene)-β-L-rhamnopyranose

Base Information

• Chemical Name: 3-O-benzyl-4-O-(4-fluorophenylthionocarbonyl)-1,2-O-(1-methoxyethylidene)-β-L-rhamnopyranose
• CAS No.: 157306-15-5
• Molecular Formula: C₂₃H₂₅FO₇S
• Molecular Weight: 464.512

Synonyms:3-O-benzyl-4-O-(4-fluorophenylthionocarbonyl)-1,2-O-(1-methoxyethylidene)-β-L-rhamnopyranose

Chemical Property of 3-O-benzyl-4-O-(4-fluorophenylthionocarbonyl)-1,2-O-(1-methoxyethylidene)-β-L-rhamnopyranose

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Technology Process of 3-O-benzyl-4-O-(4-fluorophenylthionocarbonyl)-1,2-O-(1-methoxyethylidene)-β-L-rhamnopyranose

There total 3 articles about 3-O-benzyl-4-O-(4-fluorophenylthionocarbonyl)-1,2-O-(1-methoxyethylidene)-β-L-rhamnopyranose 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: 70.0%

4-fluorophenyl chlorothionoformate (42908-73-6) + 3-O-benzyl-1,2-O-(1-methoxyethylidene)-β-L-rhamnopyranose (157306-14-4) → 3-O-benzyl-4-O-(4-fluorophenylthionocarbonyl)-1,2-O-(1-methoxyethylidene)-β-L-rhamnopyranose (157306-15-5)

Guidance literature:

With pyridine; 1-hydroxy-pyrrolidine-2,5-dione; In tetrahydrofuran; for 3h; Ambient temperature;

DOI:10.1016/0008-6215(94)80045-6

Reference yield:

benzyl bromide (100-39-0) → 3-O-benzyl-4-O-(4-fluorophenylthionocarbonyl)-1,2-O-(1-methoxyethylidene)-β-L-rhamnopyranose (157306-15-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) Bu₂SnO, 2.) Bu₄NBr / 1.) benzene, reflux, 3 h, 2.) benzene, from 80 to 90 deg C, 18 h

2: 70 percent / pyridine, N-hydroxysuccinimide / tetrahydrofuran / 3 h / Ambient temperature

With pyridine; 1-hydroxy-pyrrolidine-2,5-dione; tetrabutylammomium bromide; di(n-butyl)tin oxide; In tetrahydrofuran;

DOI:10.1016/0008-6215(94)80045-6

Reference yield:

1,2-O-(1-methoxyethylidene)-β-L-rhamnopyranose (80851-14-5) → 3-O-benzyl-4-O-(4-fluorophenylthionocarbonyl)-1,2-O-(1-methoxyethylidene)-β-L-rhamnopyranose (157306-15-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) Bu₂SnO, 2.) Bu₄NBr / 1.) benzene, reflux, 3 h, 2.) benzene, from 80 to 90 deg C, 18 h

2: 70 percent / pyridine, N-hydroxysuccinimide / tetrahydrofuran / 3 h / Ambient temperature

With pyridine; 1-hydroxy-pyrrolidine-2,5-dione; tetrabutylammomium bromide; di(n-butyl)tin oxide; In tetrahydrofuran;

DOI:10.1016/0008-6215(94)80045-6

upstream raw materials:

4-fluorophenyl chlorothionoformate

3-O-benzyl-1,2-O-(1-methoxyethylidene)-β-L-rhamnopyranose

benzyl bromide

1,2-O-(1-methoxyethylidene)-β-L-rhamnopyranose

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