(2R,3S,4R,5R,6R)-5-Acetylamino-6-[(S)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-2-fluoro-4-hydroxy-3-phenylsulfanyl-tetrahydro-pyran-2-carboxylic acid methyl ester

Base Information

Chemical Name:(2R,3S,4R,5R,6R)-5-Acetylamino-6-[(S)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-2-fluoro-4-hydroxy-3-phenylsulfanyl-tetrahydro-pyran-2-carboxylic acid methyl ester
CAS No.:146788-04-7
Molecular Formula:C₂₁H₂₈FNO₈S
Molecular Weight:473.52
Hs Code.:

(2R,3S,4R,5R,6R)-5-Acetylamino-6-[(S)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-2-fluoro-4-hydroxy-3-phenylsulfanyl-tetrahydro-pyran-2-carboxylic acid methyl ester

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Chemical Property of (2R,3S,4R,5R,6R)-5-Acetylamino-6-[(S)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-2-fluoro-4-hydroxy-3-phenylsulfanyl-tetrahydro-pyran-2-carboxylic acid methyl ester

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Technology Process of (2R,3S,4R,5R,6R)-5-Acetylamino-6-[(S)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-2-fluoro-4-hydroxy-3-phenylsulfanyl-tetrahydro-pyran-2-carboxylic acid methyl ester

There total 4 articles about (2R,3S,4R,5R,6R)-5-Acetylamino-6-[(S)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-2-fluoro-4-hydroxy-3-phenylsulfanyl-tetrahydro-pyran-2-carboxylic acid methyl 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: 76.0%

: 67-64-1
acetone

: 146815-47-6
(2R,3S,4R,5R,6R)-5-Acetylamino-2-fluoro-4-hydroxy-3-phenylsulfanyl-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester

: 146788-04-7
(2R,3S,4R,5R,6R)-5-Acetylamino-6-[(S)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-2-fluoro-4-hydroxy-3-phenylsulfanyl-tetrahydro-pyran-2-carboxylic acid methyl ester

Guidance literature:: With Dowex 50Wx₈ (H(+)-form); for 6h; Ambient temperature;
DOI:10.1080/07328309608005696

Reference yield:

: 120104-58-7
(2S,3S,4R,5S,6R)-4-Acetoxy-5-acetylamino-2-chloro-3-phenylsulfanyl-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester

: 146788-04-7
(2R,3S,4R,5R,6R)-5-Acetylamino-6-[(S)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-2-fluoro-4-hydroxy-3-phenylsulfanyl-tetrahydro-pyran-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: AgOTf, aq. Na₂HPO₄ / acetonitrile / 1.) r.t., 30 min, 2.) 50 deg C, 22 h

2: DAST / CH₂Cl₂ / 1 h / -78 °C

3: 91 percent / t-BuOK / methanol / 3 h / Ambient temperature

4: 76 percent / Dowex 50Wx₈ (H(+)-form) / 6 h / Ambient temperature

With disodium hydrogenphosphate; Dowex 50Wx₈ (H(+)-form); potassium tert-butylate; silver trifluoromethanesulfonate; 4,4'-diaminostilbene-2,2'-disulfonic acid; In methanol; dichloromethane; acetonitrile;
DOI:10.1080/07328309608005696

Reference yield:

: 146815-46-5
(2R,3S,4R,5S,6R)-4-Acetoxy-5-acetylamino-2-fluoro-3-phenylsulfanyl-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester

: 146788-04-7
(2R,3S,4R,5R,6R)-5-Acetylamino-6-[(S)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-2-fluoro-4-hydroxy-3-phenylsulfanyl-tetrahydro-pyran-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 91 percent / t-BuOK / methanol / 3 h / Ambient temperature

2: 76 percent / Dowex 50Wx₈ (H(+)-form) / 6 h / Ambient temperature

With Dowex 50Wx₈ (H(+)-form); potassium tert-butylate; In methanol;
DOI:10.1080/07328309608005696