(3R,4S,6S)-4-((R)-1-(benzyloxy)propan-2-yl)-6-((S)-1-((tertbutyldimethylsilyl)oxy)propan-2-yl)-3,4-dihydroxy-tetrahydropyran-2-one

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Chemical Name:(3R,4S,6S)-4-((R)-1-(benzyloxy)propan-2-yl)-6-((S)-1-((tertbutyldimethylsilyl)oxy)propan-2-yl)-3,4-dihydroxy-tetrahydropyran-2-one
CAS No.:1421359-37-6
Molecular Formula:C₂₄H₄₀O₆Si
Molecular Weight:452.663
Hs Code.:

Synonyms:(3R,4S,6S)-4-((R)-1-(benzyloxy)propan-2-yl)-6-((S)-1-((tertbutyldimethylsilyl)oxy)propan-2-yl)-3,4-dihydroxy-tetrahydropyran-2-one

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Chemical Property of (3R,4S,6S)-4-((R)-1-(benzyloxy)propan-2-yl)-6-((S)-1-((tertbutyldimethylsilyl)oxy)propan-2-yl)-3,4-dihydroxy-tetrahydropyran-2-one

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Technology Process of (3R,4S,6S)-4-((R)-1-(benzyloxy)propan-2-yl)-6-((S)-1-((tertbutyldimethylsilyl)oxy)propan-2-yl)-3,4-dihydroxy-tetrahydropyran-2-one

There total 8 articles about (3R,4S,6S)-4-((R)-1-(benzyloxy)propan-2-yl)-6-((S)-1-((tertbutyldimethylsilyl)oxy)propan-2-yl)-3,4-dihydroxy-tetrahydropyran-2-one 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: 97.0%

: 1421359-34-3
(S)-4-((S)-1-(benzyloxy)propan-2-yl)-6-((S)-1-((tert-butyldimethylsilyl)oxy)propan-2-yl)-5,6-dihydropyran-2-one

: 1421359-37-6
(3R,4S,6S)-4-((R)-1-(benzyloxy)propan-2-yl)-6-((S)-1-((tertbutyldimethylsilyl)oxy)propan-2-yl)-3,4-dihydroxy-tetrahydropyran-2-one

Guidance literature:: With potassium osmate(VI) dihydrate; 4-methylmorpholine N-oxide; In water; acetone; at 20 ℃; for 16h;
DOI:10.1021/jo302440a

Reference yield:

: 565454-94-6
(S)-(4-(benzyloxy)-3-methyl-2-methylenebutyl)trimethylsilane

: 1421359-37-6
(3R,4S,6S)-4-((R)-1-(benzyloxy)propan-2-yl)-6-((S)-1-((tertbutyldimethylsilyl)oxy)propan-2-yl)-3,4-dihydroxy-tetrahydropyran-2-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: tin(IV) chloride / dichloromethane / 1 h / -78 °C

1.2: 0.83 h / -78 °C

2.1: triethylamine / dichloromethane / 2 h / 0 - 20 °C

3.1: Hoveyda-Grubbs catalyst second generation / toluene / Reflux

4.1: potassium osmate(VI) dihydrate; 4-methylmorpholine N-oxide / acetone; water / 16 h / 20 °C

With potassium osmate(VI) dihydrate; Hoveyda-Grubbs catalyst second generation; tin(IV) chloride; 4-methylmorpholine N-oxide; triethylamine; In dichloromethane; water; acetone; toluene;
DOI:10.1021/jo302440a

Reference yield:

: 81927-55-1
O-benzyl 2,2,2-trichloroacetimidate

: 1421359-37-6
(3R,4S,6S)-4-((R)-1-(benzyloxy)propan-2-yl)-6-((S)-1-((tertbutyldimethylsilyl)oxy)propan-2-yl)-3,4-dihydroxy-tetrahydropyran-2-one

Guidance literature:: Multi-step reaction with 7 steps

1.1: trifluorormethanesulfonic acid / dichloromethane; cyclohexane / 48 h / 0 - 20 °C

2.1: cerium(III) chloride heptahydrate / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

2.2: 20 °C

3.1: amberlyst15 / hexane / 1 h / 20 °C

4.1: tin(IV) chloride / dichloromethane / 1 h / -78 °C

4.2: 0.83 h / -78 °C

5.1: triethylamine / dichloromethane / 2 h / 0 - 20 °C

6.1: Hoveyda-Grubbs catalyst second generation / toluene / Reflux

7.1: potassium osmate(VI) dihydrate; 4-methylmorpholine N-oxide / acetone; water / 16 h / 20 °C

With potassium osmate(VI) dihydrate; Hoveyda-Grubbs catalyst second generation; trifluorormethanesulfonic acid; cerium(III) chloride heptahydrate; tin(IV) chloride; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; hexane; dichloromethane; cyclohexane; water; acetone; toluene;
DOI:10.1021/jo302440a