(3'S, 4'R)-1,2-O-isopropylidene-3-O-(3'-dimethylphenylsilylazetidin-2'-on-4'-yl)-α-D-xylofuranose

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Chemical Name:(3'S, 4'R)-1,2-O-isopropylidene-3-O-(3'-dimethylphenylsilylazetidin-2'-on-4'-yl)-α-D-xylofuranose
CAS No.:218146-86-2
Molecular Formula:C₁₉H₂₇NO₆Si
Molecular Weight:393.512
Hs Code.:

Synonyms:(3'S, 4'R)-1,2-O-isopropylidene-3-O-(3'-dimethylphenylsilylazetidin-2'-on-4'-yl)-α-D-xylofuranose

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Chemical Property of (3'S, 4'R)-1,2-O-isopropylidene-3-O-(3'-dimethylphenylsilylazetidin-2'-on-4'-yl)-α-D-xylofuranose

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Technology Process of (3'S, 4'R)-1,2-O-isopropylidene-3-O-(3'-dimethylphenylsilylazetidin-2'-on-4'-yl)-α-D-xylofuranose

There total 7 articles about (3'S, 4'R)-1,2-O-isopropylidene-3-O-(3'-dimethylphenylsilylazetidin-2'-on-4'-yl)-α-D-xylofuranose 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: 72.0%

: 218146-84-0
(3'S, 4'R)-1,2-O-isopropylidene-3-O-(3'-dimethylphenylsilylazetidin-2'-on-4'-yl)-5-O-trityl-α-D-xylofuranose

: 218146-86-2
(3'S, 4'R)-1,2-O-isopropylidene-3-O-(3'-dimethylphenylsilylazetidin-2'-on-4'-yl)-α-D-xylofuranose

Guidance literature:: With toluene-4-sulfonic acid; In methanol; at 20 ℃; for 5h;
DOI:10.1016/S0040-4020(98)00857-6

Reference yield:

: 20590-53-8
1,2-O-isopropylidene-5-O-trityl-α-D-xylofuranose

: 218146-86-2
(3'S, 4'R)-1,2-O-isopropylidene-3-O-(3'-dimethylphenylsilylazetidin-2'-on-4'-yl)-α-D-xylofuranose

Guidance literature:: Multi-step reaction with 6 steps

2.1: n-BuLi / tetrahydrofuran; hexane / -50 - -20 °C

2.2: tetrahydrofuran; hexane / -20 - 20 °C

3.1: 97 percent / H₂; quinoline / Pd/BaSO₄ / hexane; ethyl acetate / 4 h

4.1: Na₂CO₃ / toluene / -78 °C

5.1: Red-Al / toluene / -78 - 0 °C

6.1: 72 percent / p-TsOH / methanol / 5 h / 20 °C

With quinoline; n-butyllithium; hydrogen; sodium carbonate; toluene-4-sulfonic acid; sodium bis(2-methoxyethoxy)aluminium dihydride; Pd-BaSO₄; In tetrahydrofuran; methanol; hexane; ethyl acetate; toluene; 2.1: Metallation / 2.2: silylation / 3.1: Catalytic hydrogenation / 4.1: Cycloaddition / 5.1: Elimination / 6.1: Hydrolysis;
DOI:10.1016/S0040-4020(98)00857-6

Reference yield:

: 768-33-2
phenyldimethylsilyl chloride

: 218146-86-2
(3'S, 4'R)-1,2-O-isopropylidene-3-O-(3'-dimethylphenylsilylazetidin-2'-on-4'-yl)-α-D-xylofuranose

Guidance literature:: Multi-step reaction with 5 steps

1.1: n-BuLi / tetrahydrofuran; hexane / -50 - -20 °C

1.2: tetrahydrofuran; hexane / -20 - 20 °C

2.1: 97 percent / H₂; quinoline / Pd/BaSO₄ / hexane; ethyl acetate / 4 h

3.1: Na₂CO₃ / toluene / -78 °C

4.1: Red-Al / toluene / -78 - 0 °C

5.1: 72 percent / p-TsOH / methanol / 5 h / 20 °C

With quinoline; n-butyllithium; hydrogen; sodium carbonate; toluene-4-sulfonic acid; sodium bis(2-methoxyethoxy)aluminium dihydride; Pd-BaSO₄; In tetrahydrofuran; methanol; hexane; ethyl acetate; toluene; 1.1: Metallation / 1.2: silylation / 2.1: Catalytic hydrogenation / 3.1: Cycloaddition / 4.1: Elimination / 5.1: Hydrolysis;
DOI:10.1016/S0040-4020(98)00857-6