(2S,3S,4S,5S)-4-Benzyloxy-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-pentyl-tetrahydro-furan-3-ol

Base Information

Chemical Name:(2S,3S,4S,5S)-4-Benzyloxy-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-pentyl-tetrahydro-furan-3-ol
CAS No.:369375-81-5
Molecular Formula:C₂₁H₃₂O₅
Molecular Weight:364.482
Hs Code.:

Synonyms:(2S,3S,4S,5S)-4-Benzyloxy-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-pentyl-tetrahydro-furan-3-ol

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Chemical Property of (2S,3S,4S,5S)-4-Benzyloxy-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-pentyl-tetrahydro-furan-3-ol

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Technology Process of (2S,3S,4S,5S)-4-Benzyloxy-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-pentyl-tetrahydro-furan-3-ol

There total 8 articles about (2S,3S,4S,5S)-4-Benzyloxy-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-pentyl-tetrahydro-furan-3-ol 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: 98.0%

: 369375-75-7
[(2R,3S,4R,5S)-4-Benzyloxy-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-pentyl-tetrahydro-furan-3-yloxy]-tert-butyl-dimethyl-silane

: 369375-81-5
(2S,3S,4S,5S)-4-Benzyloxy-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-pentyl-tetrahydro-furan-3-ol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran;
DOI:10.1016/S0957-4166(01)00244-0

Reference yield:

: 693-25-4
n-pentylmagnesium bromide

: 369375-81-5
(2S,3S,4S,5S)-4-Benzyloxy-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-pentyl-tetrahydro-furan-3-ol

Guidance literature:: Multi-step reaction with 3 steps

1: CeCl₃ / tetrahydrofuran / 2 h / -78 °C

2: 0.091 g / Et₃SiH; BF₃*OEt₂ / CH₂Cl₂ / 2 h / -78 °C

3: 98 percent / Bu₄NF / tetrahydrofuran

With triethylsilane; cerium(III) chloride; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; In tetrahydrofuran; dichloromethane; 1: Grignard reaction;
DOI:10.1016/S0957-4166(01)00244-0

Reference yield:

: 100-39-0
benzyl bromide

: 369375-81-5
(2S,3S,4S,5S)-4-Benzyloxy-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-pentyl-tetrahydro-furan-3-ol

Guidance literature:: Multi-step reaction with 5 steps

1: 50 percent / Ag₂O / ethyl acetate

2: 92 percent / imidazole / CH₂Cl₂

3: CeCl₃ / tetrahydrofuran / 2 h / -78 °C

4: 0.091 g / Et₃SiH; BF₃*OEt₂ / CH₂Cl₂ / 2 h / -78 °C

5: 98 percent / Bu₄NF / tetrahydrofuran

With 1H-imidazole; triethylsilane; cerium(III) chloride; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; silver(l) oxide; In tetrahydrofuran; dichloromethane; ethyl acetate; 3: Grignard reaction;
DOI:10.1016/S0957-4166(01)00244-0