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

Base Information

Chemical Name: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
CAS No.:1418193-74-4
Molecular Formula:C₂₅H₄₂O₉SSi
Molecular Weight:546.755
Hs Code.:

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 7 articles about 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 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: 93.0%

: 1418193-73-3
methyl 2-((4R,5R,6R)-6-{(1R,2R)-2-[(tert-butyldimethylsilyl)oxy]-1-methoxy-2-phenylethyl}-5-hydroxy-2,2-dimethyl-1,3-dioxan-4-yl)acetate

: 124-63-0
methanesulfonyl chloride

: 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

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 0 - 20 ℃; for 2.5h;
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

: 1418193-74-4
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

Guidance literature:: Multi-step reaction with 2 steps

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

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

With dmap; zinc(II) tetrahydroborate; triethylamine; In 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

: 1418193-74-4
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

Guidance literature:: Multi-step reaction with 4 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

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