((2S,3S)-2-Hydroxymethyl-5-phenylsulfanyl-tetrahydro-furan-3-ylmethyl)-phosphonic acid diethyl ester

Base Information

• Chemical Name: ((2S,3S)-2-Hydroxymethyl-5-phenylsulfanyl-tetrahydro-furan-3-ylmethyl)-phosphonic acid diethyl ester
• CAS No.: 220222-88-8
• Molecular Formula: C₁₆H₂₅O₅PS
• Molecular Weight: 360.411

Synonyms:((2S,3S)-2-Hydroxymethyl-5-phenylsulfanyl-tetrahydro-furan-3-ylmethyl)-phosphonic acid diethyl ester

Chemical Property of ((2S,3S)-2-Hydroxymethyl-5-phenylsulfanyl-tetrahydro-furan-3-ylmethyl)-phosphonic acid diethyl ester

Chemical Property:

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Technology Process of ((2S,3S)-2-Hydroxymethyl-5-phenylsulfanyl-tetrahydro-furan-3-ylmethyl)-phosphonic acid diethyl ester

There total 3 articles about ((2S,3S)-2-Hydroxymethyl-5-phenylsulfanyl-tetrahydro-furan-3-ylmethyl)-phosphonic 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: 90.0%

Benzoic acid (2S,3S)-3-(diethoxy-phosphorylmethyl)-5-phenylsulfanyl-tetrahydro-furan-2-ylmethyl ester (220222-87-7) → ((2S,3S)-2-Hydroxymethyl-5-phenylsulfanyl-tetrahydro-furan-3-ylmethyl)-phosphonic acid diethyl ester (220222-88-8)

Guidance literature:

With ammonium hydroxide; In pyridine;

DOI:10.3987/com-98-s(h)8

Reference yield:

phenylthiotrimethylsilane (4551-15-9) → ((2S,3S)-2-Hydroxymethyl-5-phenylsulfanyl-tetrahydro-furan-3-ylmethyl)-phosphonic acid diethyl ester (220222-88-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / TMSOTf / CH₂Cl₂ / 0 °C

2: 90 percent / NH₄OH / pyridine

With ammonium hydroxide; trimethylsilyl trifluoromethanesulfonate; In pyridine; dichloromethane; 1: Thioetherification / 2: Hydrolysis;

DOI:10.3987/com-98-s(h)8

Reference yield:

Benzoic acid (2S,3S)-3-(diethoxy-phosphorylmethyl)-5-ethoxy-tetrahydro-furan-2-ylmethyl ester → ((2S,3S)-2-Hydroxymethyl-5-phenylsulfanyl-tetrahydro-furan-3-ylmethyl)-phosphonic acid diethyl ester (220222-88-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / TMSOTf / CH₂Cl₂ / 0 °C

2: 90 percent / NH₄OH / pyridine

With ammonium hydroxide; trimethylsilyl trifluoromethanesulfonate; In pyridine; dichloromethane; 1: Thioetherification / 2: Hydrolysis;

DOI:10.3987/com-98-s(h)8

upstream raw materials:

Benzoic acid (2S,3S)-3-(diethoxy-phosphorylmethyl)-5-phenylsulfanyl-tetrahydro-furan-2-ylmethyl ester

phenylthiotrimethylsilane

Downstream raw materials:

[(2S,3S)-2-(4-Methoxy-pyrimidin-2-yloxymethyl)-5-phenylsulfanyl-tetrahydro-furan-3-ylmethyl]-phosphonic acid diethyl ester

[(2S,3S)-2-(4-Methoxy-5-methyl-pyrimidin-2-yloxymethyl)-5-phenylsulfanyl-tetrahydro-furan-3-ylmethyl]-phosphonic acid diethyl ester

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