(2S,3R,4R,5S)-3-Benzyloxy-6-fluoro-4,5-dimethoxy-2-methyl-tetrahydro-pyran

Base Information

• Chemical Name: (2S,3R,4R,5S)-3-Benzyloxy-6-fluoro-4,5-dimethoxy-2-methyl-tetrahydro-pyran
• CAS No.: 861120-58-3
• Molecular Formula: C₁₅H₂₁FO₄
• Molecular Weight: 284.328

Synonyms:(2S,3R,4R,5S)-3-Benzyloxy-6-fluoro-4,5-dimethoxy-2-methyl-tetrahydro-pyran

Chemical Property of (2S,3R,4R,5S)-3-Benzyloxy-6-fluoro-4,5-dimethoxy-2-methyl-tetrahydro-pyran

Chemical Property:

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Technology Process of (2S,3R,4R,5S)-3-Benzyloxy-6-fluoro-4,5-dimethoxy-2-methyl-tetrahydro-pyran

There total 4 articles about (2S,3R,4R,5S)-3-Benzyloxy-6-fluoro-4,5-dimethoxy-2-methyl-tetrahydro-pyran 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: 82.0%

(2S,3R,4R,5S)-3-Benzyloxy-4,5-dimethoxy-2-methyl-6-phenylsulfanyl-tetrahydro-pyran → (2S,3R,4R,5S)-3-Benzyloxy-6-fluoro-4,5-dimethoxy-2-methyl-tetrahydro-pyran (861120-58-3)

Guidance literature:

With (C₂H₅)NSF₃,NBS; In dichloromethane; at -15 ℃; for 0.5h;

DOI:10.1246/cl.1995.855

Reference yield: 81.0%

(2S,3R,4R,5S,6R)-3-Benzyloxy-4,5-dimethoxy-2-methyl-6-phenylsulfanyl-tetrahydro-pyran (163494-00-6) → (2S,3R,4R,5S)-3-Benzyloxy-6-fluoro-4,5-dimethoxy-2-methyl-tetrahydro-pyran (861120-58-3)

Guidance literature:

With N-Bromosuccinimide; In dichloromethane; at 0 ℃;

DOI:10.1021/jo0503862

Reference yield:

benzyl bromide (100-39-0) → (2S,3R,4R,5S)-3-Benzyloxy-6-fluoro-4,5-dimethoxy-2-methyl-tetrahydro-pyran (861120-58-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 74 percent / NaH / tetrahydrofuran / 0 °C

2: 81 percent / Et₃NSF₃; NBS / CH₂Cl₂ / 0 °C

With N-Bromosuccinimide; sodium hydride; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo0503862

upstream raw materials:

(2S,3R,4R,5S,6R)-3-Benzyloxy-4,5-dimethoxy-2-methyl-6-phenylsulfanyl-tetrahydro-pyran

benzyl bromide

phenyl 2,3-di-O-methyl-1-thio-β-L-fucopyranoside

Downstream raw materials:

(2S,3R,4R,5S,6S)-3-Benzyloxy-6-((2R,3R,4S,5R)-3,5-dimethoxy-2-phenylsulfanyl-tetrahydro-pyran-4-yloxy)-4,5-dimethoxy-2-methyl-tetrahydro-pyran

3-[4-O-benzyl-2,3-di-O-methyl-α-L-fucopyranosyl]-2,4-di-O-methyl-1-thiophenyl-β-D-xylopyranose

Acetic acid (2S,3R,4S,5R)-5-acetoxy-4-((2S,3S,4R,5R,6S)-5-benzyloxy-3,4-dimethoxy-6-methyl-tetrahydro-pyran-2-yloxy)-2-phenylsulfanyl-tetrahydro-pyran-3-yl ester

{(2R,3R,4R,6R)-6-Acetoxymethyl-4-[(2S,3R,4S,5R)-4-((2S,3S,4R,5R,6S)-5-benzyloxy-3,4-dimethoxy-6-methyl-tetrahydro-pyran-2-yloxy)-3,5-dimethoxy-tetrahydro-pyran-2-yloxy]-3-methyl-tetrahydro-pyran-2-yl}-acetic acid methyl ester

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