5-((2S,3S,4R,5S,6S)-3,4,5-Trihydroxy-6-methyl-tetrahydro-pyran-2-ylsulfanylmethyl)-isophthalic acid diethyl ester

Base Information

• Chemical Name: 5-((2S,3S,4R,5S,6S)-3,4,5-Trihydroxy-6-methyl-tetrahydro-pyran-2-ylsulfanylmethyl)-isophthalic acid diethyl ester
• CAS No.: 374678-24-7
• Molecular Formula: C₁₉H₂₆O₈S
• Molecular Weight: 414.477

Synonyms:5-((2S,3S,4R,5S,6S)-3,4,5-Trihydroxy-6-methyl-tetrahydro-pyran-2-ylsulfanylmethyl)-isophthalic acid diethyl ester

Chemical Property of 5-((2S,3S,4R,5S,6S)-3,4,5-Trihydroxy-6-methyl-tetrahydro-pyran-2-ylsulfanylmethyl)-isophthalic acid diethyl ester

Chemical Property:

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Technology Process of 5-((2S,3S,4R,5S,6S)-3,4,5-Trihydroxy-6-methyl-tetrahydro-pyran-2-ylsulfanylmethyl)-isophthalic acid diethyl ester

There total 2 articles about 5-((2S,3S,4R,5S,6S)-3,4,5-Trihydroxy-6-methyl-tetrahydro-pyran-2-ylsulfanylmethyl)-isophthalic acid diethyl ester 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: 92.0%

2,3,4-tri-O-acetyl-1,S-acetyl-1-thio-α-L-fucopyranose (151895-52-2) + 5-(bromomethyl)isophthalic acid diethyl ester (156750-11-7) → 5-((2S,3S,4R,5S,6S)-3,4,5-Trihydroxy-6-methyl-tetrahydro-pyran-2-ylsulfanylmethyl)-isophthalic acid diethyl ester (374678-24-7)

Guidance literature:

With sodium ethanolate; In ethanol;

DOI:10.1016/S0960-894X(01)00430-9

Reference yield:

diethyl 5-(hydroxymethyl)isophthalate (181425-91-2) → 5-((2S,3S,4R,5S,6S)-3,4,5-Trihydroxy-6-methyl-tetrahydro-pyran-2-ylsulfanylmethyl)-isophthalic acid diethyl ester (374678-24-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 83 percent / PPh₃; CBr₄ / CH₂Cl₂

2: 92 percent / 20 percent NaOEt / ethanol

With carbon tetrabromide; sodium ethanolate; triphenylphosphine; In ethanol; dichloromethane;

DOI:10.1016/S0960-894X(01)00430-9

Reference yield: 90.0%

5-((2S,3S,4R,5S,6S)-3,4,5-Trihydroxy-6-methyl-tetrahydro-pyran-2-ylsulfanylmethyl)-isophthalic acid diethyl ester (374678-24-7) → 5-((2S,3S,4R,5S,6S)-3,4,5-Trihydroxy-6-methyl-tetrahydro-pyran-2-ylsulfanylmethyl)-isophthalic acid monoethyl ester (374678-25-8)

Guidance literature:

With potassium hydroxide; In ethanol;

DOI:10.1016/S0960-894X(01)00430-9

upstream raw materials:

2,3,4-tri-O-acetyl-1,S-acetyl-1-thio-α-L-fucopyranose

5-(bromomethyl)isophthalic acid diethyl ester

diethyl 5-(hydroxymethyl)isophthalate

Downstream raw materials:

5-((2S,3S,4R,5S,6S)-3,4,5-Trihydroxy-6-methyl-tetrahydro-pyran-2-ylsulfanylmethyl)-isophthalic acid monoethyl ester

N-(2-Tetradecyl-hexadecyl)-5-((2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-ylsulfanylmethyl)-isophthalamic acid ethyl ester

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