4-(3,4-di-O-benzyl-2,6-dideoxy-β-D-arabino-hexopyranosyl)-2-iodo-3-methoxyphenyl trifluoromethanesulfonate

Base Information

• Chemical Name: 4-(3,4-di-O-benzyl-2,6-dideoxy-β-D-arabino-hexopyranosyl)-2-iodo-3-methoxyphenyl trifluoromethanesulfonate
• CAS No.: 171081-02-0
• Molecular Formula: C₂₈H₂₈F₃IO₇S
• Molecular Weight: 692.492

Synonyms:4-(3,4-di-O-benzyl-2,6-dideoxy-β-D-arabino-hexopyranosyl)-2-iodo-3-methoxyphenyl trifluoromethanesulfonate

Chemical Property of 4-(3,4-di-O-benzyl-2,6-dideoxy-β-D-arabino-hexopyranosyl)-2-iodo-3-methoxyphenyl trifluoromethanesulfonate

Chemical Property:

Purity/Quality:

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Technology Process of 4-(3,4-di-O-benzyl-2,6-dideoxy-β-D-arabino-hexopyranosyl)-2-iodo-3-methoxyphenyl trifluoromethanesulfonate

There total 6 articles about 4-(3,4-di-O-benzyl-2,6-dideoxy-β-D-arabino-hexopyranosyl)-2-iodo-3-methoxyphenyl trifluoromethanesulfonate 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: 98.6%

trifluoromethylsulfonic anhydride (358-23-6) + 4-(3,4-di-O-benzyl-2,6-dideoxy-β-D-arabino-hexopyranosyl)-2-iodo-3-methoxyphenol → 4-(3,4-di-O-benzyl-2,6-dideoxy-β-D-arabino-hexopyranosyl)-2-iodo-3-methoxyphenyl trifluoromethanesulfonate (171081-02-0)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at -78 ℃;

DOI:10.1246/cl.1995.677

Reference yield:

2-iodo-3-(methoxymethoxy)phenol (121980-53-8) → 4-(3,4-di-O-benzyl-2,6-dideoxy-β-D-arabino-hexopyranosyl)-2-iodo-3-methoxyphenyl trifluoromethanesulfonate (171081-02-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 91.7 percent / imidazole / dimethylformamide / 0.5 h / 20 °C

2.1: 97.6 percent / aq. H₂SO₄ / dioxane / 5 h / 55 °C

3.1: 94.6 percent / Cp₂HfCl₂; AgClO₄; 4A molecular sieves / CH₂Cl₂ / 0.92 h / -78 - 0 °C

4.1: NaH / tetrahydrofuran / 0.17 h / 0 °C

4.2: 95.6 percent / tetrahydrofuran; dimethylformamide / 1 h / 20 °C

5.1: 99.6 percent / TBAF / tetrahydrofuran / 0.33 h / 0 °C

6.1: 98.6 percent / i-Pr₂NEt / CH₂Cl₂ / 0.25 h / -78 °C

With 1H-imidazole; bis(cyclopentadienyl)hafnium dichloride; 4 A molecular sieve; sulfuric acid; tetrabutyl ammonium fluoride; silver perchlorate; sodium hydride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide; 1.1: silylation / 2.1: Hydrolysis / 3.1: glycosylation / 4.1: Metallation / 4.2: Methylation / 5.1: desilylation / 6.1: Esterification;

DOI:10.1016/S0040-4020(97)01034-X

Reference yield:

3-(tert-butyldiphenylsilyloxy)-2-iodophenol (171080-98-1) → 4-(3,4-di-O-benzyl-2,6-dideoxy-β-D-arabino-hexopyranosyl)-2-iodo-3-methoxyphenyl trifluoromethanesulfonate (171081-02-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 94.6 percent / Cp₂HfCl₂; AgClO₄; 4A molecular sieves / CH₂Cl₂ / 0.92 h / -78 - 0 °C

2.1: NaH / tetrahydrofuran / 0.17 h / 0 °C

2.2: 95.6 percent / tetrahydrofuran; dimethylformamide / 1 h / 20 °C

3.1: 99.6 percent / TBAF / tetrahydrofuran / 0.33 h / 0 °C

4.1: 98.6 percent / i-Pr₂NEt / CH₂Cl₂ / 0.25 h / -78 °C

With bis(cyclopentadienyl)hafnium dichloride; 4 A molecular sieve; tetrabutyl ammonium fluoride; silver perchlorate; sodium hydride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; 1.1: glycosylation / 2.1: Metallation / 2.2: Methylation / 3.1: desilylation / 4.1: Esterification;

DOI:10.1016/S0040-4020(97)01034-X

upstream raw materials:

trifluoromethylsulfonic anhydride

2-iodo-3-(methoxymethoxy)phenol

3-(tert-butyldiphenylsilyloxy)-2-iodophenol

3-(tert-butyldiphenylsilyloxy)-2-iodo-1-(methoxymethoxy)benzene

Downstream raw materials:

6-(3,4-di-O-benzyl-2,6-dideoxy-β-D-arabino-hexopyranosyl)-5-methoxy-1,4-naphthoquinone

2-chloro-6-(3,4-di-O-benzyl-2,6-dideoxy-β-D-arabino-hexopyranosyl)-5-methoxy-1,4-naphthoquinone

4-((2R,4R,5R,6R)-4,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-5,8-dimethoxy-bicyclo[4.2.0]octa-1⁽⁶⁾,2,4-trien-7-one

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