(2S,3R,4R)-4-hydroxy-2-[(1S,2R)-2-hydroxy-1-methoxy-2-phenylethyl]-6-oxotetrahydro-2H-pyran-3-yl methanesulfonate

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Chemical Name:(2S,3R,4R)-4-hydroxy-2-[(1S,2R)-2-hydroxy-1-methoxy-2-phenylethyl]-6-oxotetrahydro-2H-pyran-3-yl methanesulfonate
CAS No.:1418193-75-5
Molecular Formula:C₁₅H₂₀O₈S
Molecular Weight:360.385
Hs Code.:

Synonyms:(2S,3R,4R)-4-hydroxy-2-[(1S,2R)-2-hydroxy-1-methoxy-2-phenylethyl]-6-oxotetrahydro-2H-pyran-3-yl methanesulfonate

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Chemical Property of (2S,3R,4R)-4-hydroxy-2-[(1S,2R)-2-hydroxy-1-methoxy-2-phenylethyl]-6-oxotetrahydro-2H-pyran-3-yl methanesulfonate

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Technology Process of (2S,3R,4R)-4-hydroxy-2-[(1S,2R)-2-hydroxy-1-methoxy-2-phenylethyl]-6-oxotetrahydro-2H-pyran-3-yl methanesulfonate

There total 7 articles about (2S,3R,4R)-4-hydroxy-2-[(1S,2R)-2-hydroxy-1-methoxy-2-phenylethyl]-6-oxotetrahydro-2H-pyran-3-yl methanesulfonate 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: 70.0%

: 1418193-74-4
methyl 2-((4R,5R,6R)-6-{(1R,2R)-2-[(tert-butyldimethylsilyl)oxy]-1-methoxy-2-phenylethyl}-2,2-dimethyl-5-[(methylsulfonyl)oxy]-1,3-dioxan-4-yl)acetate

: 1418193-75-5
(2S,3R,4R)-4-hydroxy-2-[(1S,2R)-2-hydroxy-1-methoxy-2-phenylethyl]-6-oxotetrahydro-2H-pyran-3-yl methanesulfonate

Guidance literature:: methyl 2-((4R,5R,6R)-6-{(1R,2R)-2-[(tert-butyldimethylsilyl)oxy]-1-methoxy-2-phenylethyl}-2,2-dimethyl-5-[(methylsulfonyl)oxy]-1,3-dioxan-4-yl)acetate; With sulfuric acid; In tetrahydrofuran; at 20 ℃;

With water; calcium carbonate; In tetrahydrofuran;
DOI:10.1055/s-0032-1316803

Reference yield:

: 1418193-72-2
methyl 2-((4R,6S)-6-{(1R,2R)-2-[(tert-butyldimethylsilyl)oxy]-1-methoxy-2-phenylethyl}-2,2-dimethyl-5-oxo-1,3-dioxan-4-yl)acetate

: 1418193-75-5
(2S,3R,4R)-4-hydroxy-2-[(1S,2R)-2-hydroxy-1-methoxy-2-phenylethyl]-6-oxotetrahydro-2H-pyran-3-yl methanesulfonate

Guidance literature:: Multi-step reaction with 3 steps

1: zinc(II) tetrahydroborate / diethyl ether / 10 h / -78 - 20 °C / Inert atmosphere

2: triethylamine; dmap / dichloromethane / 2.5 h / 0 - 20 °C

3: sulfuric acid / tetrahydrofuran / 20 °C

With dmap; zinc(II) tetrahydroborate; sulfuric acid; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1055/s-0032-1316803

Reference yield:

: (2R)-N-((R)-4-{(1R,2R)-2-[(tert-butyldimethylsilyl)oxy]-1-methoxy-2-phenylethyl}-2,2-dimethyl-1,3-dioxan-5-ylidene)-2-(methoxymethyl)cyclopentanamine

: 1418193-75-5
(2S,3R,4R)-4-hydroxy-2-[(1S,2R)-2-hydroxy-1-methoxy-2-phenylethyl]-6-oxotetrahydro-2H-pyran-3-yl methanesulfonate

Guidance literature:: Multi-step reaction with 5 steps

1.1: tert.-butyl lithium / tetrahydrofuran; pentane / 2 h / -78 °C / Inert atmosphere

1.2: 17 h / -100 - 20 °C / Inert atmosphere

2.1: ozone / dichloromethane / 0.25 h / -78 °C / Inert atmosphere

3.1: zinc(II) tetrahydroborate / diethyl ether / 10 h / -78 - 20 °C / Inert atmosphere

4.1: triethylamine; dmap / dichloromethane / 2.5 h / 0 - 20 °C

5.1: sulfuric acid / tetrahydrofuran / 20 °C

With dmap; zinc(II) tetrahydroborate; sulfuric acid; tert.-butyl lithium; ozone; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; pentane;
DOI:10.1055/s-0032-1316803