5-C-(1,2,3,4-tetrahydro-2,5,8-trihydroxy-4-oxo-2-naphthyl)-1,2-O-(1-methylethylidene)-3-(phenylmethoxy)-L-threofuranose

Base Information

• Chemical Name: 5-C-(1,2,3,4-tetrahydro-2,5,8-trihydroxy-4-oxo-2-naphthyl)-1,2-O-(1-methylethylidene)-3-(phenylmethoxy)-L-threofuranose
• CAS No.: 128359-88-6
• Molecular Formula: C₂₄H₂₆O₈
• Molecular Weight: 442.466

Synonyms:5-C-(1,2,3,4-tetrahydro-2,5,8-trihydroxy-4-oxo-2-naphthyl)-1,2-O-(1-methylethylidene)-3-(phenylmethoxy)-L-threofuranose

Chemical Property of 5-C-(1,2,3,4-tetrahydro-2,5,8-trihydroxy-4-oxo-2-naphthyl)-1,2-O-(1-methylethylidene)-3-(phenylmethoxy)-L-threofuranose

Chemical Property:

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Technology Process of 5-C-(1,2,3,4-tetrahydro-2,5,8-trihydroxy-4-oxo-2-naphthyl)-1,2-O-(1-methylethylidene)-3-(phenylmethoxy)-L-threofuranose

There total 3 articles about 5-C-(1,2,3,4-tetrahydro-2,5,8-trihydroxy-4-oxo-2-naphthyl)-1,2-O-(1-methylethylidene)-3-(phenylmethoxy)-L-threofuranose 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: 69.2%

5-C-(2-(2-acetyl-3,6-dihydroxyphenyl)-1-((trimethylsilyl)oxy)ethenyl)-1,2-O-(1-methylethylidene)-3-(phenylmethoxy)-L-threofuranose (128359-87-5) → 5-C-(1,2,3,4-tetrahydro-2,5,8-trihydroxy-4-oxo-2-naphthyl)-1,2-O-(1-methylethylidene)-3-(phenylmethoxy)-L-threofuranose (128359-88-6)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; dichloromethane; at 25 ℃; for 8h;

DOI:10.1021/jo00303a031

Reference yield:

2-Acetyl-1,4-benzoquinone (1125-55-9) → 5-C-(1,2,3,4-tetrahydro-2,5,8-trihydroxy-4-oxo-2-naphthyl)-1,2-O-(1-methylethylidene)-3-(phenylmethoxy)-L-threofuranose (128359-88-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 70.1 percent / acetonitrile / 8 h / 25 °C

2: 69.2 percent / Bu₄NF / CH₂Cl₂; tetrahydrofuran / 8 h / 25 °C

With tetrabutyl ammonium fluoride; In tetrahydrofuran; dichloromethane; acetonitrile;

DOI:10.1021/jo00303a031

Reference yield:

[1-((3aR,5S,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-vinyloxy]-trimethyl-silane (128359-86-4) → 5-C-(1,2,3,4-tetrahydro-2,5,8-trihydroxy-4-oxo-2-naphthyl)-1,2-O-(1-methylethylidene)-3-(phenylmethoxy)-L-threofuranose (128359-88-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 70.1 percent / acetonitrile / 8 h / 25 °C

2: 69.2 percent / Bu₄NF / CH₂Cl₂; tetrahydrofuran / 8 h / 25 °C

With tetrabutyl ammonium fluoride; In tetrahydrofuran; dichloromethane; acetonitrile;

DOI:10.1021/jo00303a031

upstream raw materials:

5-C-(2-(2-acetyl-3,6-dihydroxyphenyl)-1-((trimethylsilyl)oxy)ethenyl)-1,2-O-(1-methylethylidene)-3-(phenylmethoxy)-L-threofuranose

2-Acetyl-1,4-benzoquinone

[1-((3aR,5S,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-vinyloxy]-trimethyl-silane

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