(3'R,4'R)-5-deoxy-1,2-O-isopropylidene-3-O:5-C-[3'-(α-hydroxy-p-bromobenzyl)-azetidin-2'-on-1',4'-di-yl]-α-D-xylofuranose

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Chemical Name:(3'R,4'R)-5-deoxy-1,2-O-isopropylidene-3-O:5-C-[3'-(α-hydroxy-p-bromobenzyl)-azetidin-2'-on-1',4'-di-yl]-α-D-xylofuranose
CAS No.:218147-02-5
Molecular Formula:C₁₈H₂₀BrNO₆
Molecular Weight:426.264
Hs Code.:

Synonyms:(3'R,4'R)-5-deoxy-1,2-O-isopropylidene-3-O:5-C-[3'-(α-hydroxy-p-bromobenzyl)-azetidin-2'-on-1',4'-di-yl]-α-D-xylofuranose

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Chemical Property of (3'R,4'R)-5-deoxy-1,2-O-isopropylidene-3-O:5-C-[3'-(α-hydroxy-p-bromobenzyl)-azetidin-2'-on-1',4'-di-yl]-α-D-xylofuranose

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Technology Process of (3'R,4'R)-5-deoxy-1,2-O-isopropylidene-3-O:5-C-[3'-(α-hydroxy-p-bromobenzyl)-azetidin-2'-on-1',4'-di-yl]-α-D-xylofuranose

There total 9 articles about (3'R,4'R)-5-deoxy-1,2-O-isopropylidene-3-O:5-C-[3'-(α-hydroxy-p-bromobenzyl)-azetidin-2'-on-1',4'-di-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: 76.0%

: 1122-91-4
4-bromo-benzaldehyde

: 218146-99-7
(3'S, 4'R)-5-deoxy-1,2-O-isopropylidene-3-O:5-C-(3'-t-butyldimethylsilylazetidin-2'-on-1',4'-di-yl)-α-D-xylofuranose

: 218147-02-5
(3'R,4'R)-5-deoxy-1,2-O-isopropylidene-3-O:5-C-[3'-(α-hydroxy-p-bromobenzyl)-azetidin-2'-on-1',4'-di-yl]-α-D-xylofuranose

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 25 ℃; for 12h;
DOI:10.1016/S0040-4020(98)00857-6

Reference yield:

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

: 218147-02-5
(3'R,4'R)-5-deoxy-1,2-O-isopropylidene-3-O:5-C-[3'-(α-hydroxy-p-bromobenzyl)-azetidin-2'-on-1',4'-di-yl]-α-D-xylofuranose

Guidance literature:: Multi-step reaction with 9 steps

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

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

3.1: 95 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: 76 percent / formic acid / diethyl ether / 20 °C

7.1: 68 percent

8.1: tetrabutylammonium bromide; K₂CO₃ / acetonitrile / Heating

9.1: 76 percent / tetrabutylammonium fluoride / tetrahydrofuran / 12 h / 25 °C

With quinoline; n-butyllithium; formic acid; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; hydrogen; sodium carbonate; potassium carbonate; sodium bis(2-methoxyethoxy)aluminium dihydride; Pd-BaSO₄; In tetrahydrofuran; diethyl ether; hexane; ethyl acetate; toluene; acetonitrile; 2.1: Metallation / 2.2: silylation / 3.1: Catalytic hydrogenation / 4.1: Cycloaddition / 5.1: Elimination / 6.1: Hydrolysis / 7.1: Tosylation / 8.1: Cyclization / 9.1: Substitution;
DOI:10.1016/S0040-4020(98)00857-6

Reference yield:

: 218146-76-0
3-O-ethynyl-1,2-O-isopropylidene-5-O-trityl-α-D-xylofuranose

: 218147-02-5
(3'R,4'R)-5-deoxy-1,2-O-isopropylidene-3-O:5-C-[3'-(α-hydroxy-p-bromobenzyl)-azetidin-2'-on-1',4'-di-yl]-α-D-xylofuranose

Guidance literature:: Multi-step reaction with 8 steps

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

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

2.1: 95 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: 76 percent / formic acid / diethyl ether / 20 °C

6.1: 68 percent

7.1: tetrabutylammonium bromide; K₂CO₃ / acetonitrile / Heating

8.1: 76 percent / tetrabutylammonium fluoride / tetrahydrofuran / 12 h / 25 °C

With quinoline; n-butyllithium; formic acid; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; hydrogen; sodium carbonate; potassium carbonate; sodium bis(2-methoxyethoxy)aluminium dihydride; Pd-BaSO₄; In tetrahydrofuran; diethyl ether; hexane; ethyl acetate; toluene; acetonitrile; 1.1: Metallation / 1.2: silylation / 2.1: Catalytic hydrogenation / 3.1: Cycloaddition / 4.1: Elimination / 5.1: Hydrolysis / 6.1: Tosylation / 7.1: Cyclization / 8.1: Substitution;
DOI:10.1016/S0040-4020(98)00857-6