(2R,3R,4S)-2-(4-benzyloxy-3-methyl-6-phenylsulfanyl-tetrahydropyran-2-yl)ethanol

Base Information

• Chemical Name: (2R,3R,4S)-2-(4-benzyloxy-3-methyl-6-phenylsulfanyl-tetrahydropyran-2-yl)ethanol
• CAS No.: 243849-47-0
• Molecular Formula: C₂₁H₂₆O₃S
• Molecular Weight: 358.502

Synonyms:(2R,3R,4S)-2-(4-benzyloxy-3-methyl-6-phenylsulfanyl-tetrahydropyran-2-yl)ethanol

Chemical Property of (2R,3R,4S)-2-(4-benzyloxy-3-methyl-6-phenylsulfanyl-tetrahydropyran-2-yl)ethanol

Chemical Property:

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Technology Process of (2R,3R,4S)-2-(4-benzyloxy-3-methyl-6-phenylsulfanyl-tetrahydropyran-2-yl)ethanol

There total 3 articles about (2R,3R,4S)-2-(4-benzyloxy-3-methyl-6-phenylsulfanyl-tetrahydropyran-2-yl)ethanol 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: 99.0%

(2R,3R,4S)-(4-benzyloxy-3-methyl-6-phenylsulfanyl-tetrahydropyran-2-yl)-acetic acid methyl ester (243849-46-9) → (2R,3R,4S)-2-(4-benzyloxy-3-methyl-6-phenylsulfanyl-tetrahydropyran-2-yl)ethanol (243849-47-0)

Guidance literature:

With diisobutylaluminium hydride; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 6h;

DOI:10.1016/S0957-4166(99)00148-2

Reference yield:

phenylthiotrimethylsilane (4551-15-9) → (2R,3R,4S)-2-(4-benzyloxy-3-methyl-6-phenylsulfanyl-tetrahydropyran-2-yl)ethanol (243849-47-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / ZnI₂, n-Bu₄NI / 1,2-dichloro-ethane / 5 h / 60 °C

2: 99 percent / DIBALH / hexane; tetrahydrofuran / 6 h / -78 - 20 °C

With tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; zinc(II) iodide; In tetrahydrofuran; hexane; 1,2-dichloro-ethane;

DOI:10.1016/S0957-4166(99)00148-2

Reference yield:

(-)-(2R,3R,4S)-4-benzyloxy-6-methoxy-3-methyl-tetrahydropyran-2-acetic acid methyl ester (243849-45-8) → (2R,3R,4S)-2-(4-benzyloxy-3-methyl-6-phenylsulfanyl-tetrahydropyran-2-yl)ethanol (243849-47-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / ZnI₂, n-Bu₄NI / 1,2-dichloro-ethane / 5 h / 60 °C

2: 99 percent / DIBALH / hexane; tetrahydrofuran / 6 h / -78 - 20 °C

With tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; zinc(II) iodide; In tetrahydrofuran; hexane; 1,2-dichloro-ethane;

DOI:10.1016/S0957-4166(99)00148-2

upstream raw materials:

(2R,3R,4S)-(4-benzyloxy-3-methyl-6-phenylsulfanyl-tetrahydropyran-2-yl)-acetic acid methyl ester

phenylthiotrimethylsilane

(-)-(2R,3R,4S)-4-benzyloxy-6-methoxy-3-methyl-tetrahydropyran-2-acetic acid methyl ester

Downstream raw materials:

(2R,3R,4S)-4-benzyloxy-2-(2-triethylsilyloxy-ethyl)-3-methyl-6-phenylsulfanyl-tetrahydropyran-2-yl

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