3-O-ethynyl-1,2-O-isopropylidene-5-O-trityl-α-D-xylofuranose

Base Information

• Chemical Name: 3-O-ethynyl-1,2-O-isopropylidene-5-O-trityl-α-D-xylofuranose
• CAS No.: 218146-76-0
• Molecular Formula: C₂₉H₂₈O₅
• Molecular Weight: 456.538
• Mol file: 218146-76-0.mol

Synonyms:3-O-ethynyl-1,2-O-isopropylidene-5-O-trityl-α-D-xylofuranose

Chemical Property of 3-O-ethynyl-1,2-O-isopropylidene-5-O-trityl-α-D-xylofuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-O-ethynyl-1,2-O-isopropylidene-5-O-trityl-α-D-xylofuranose

There total 1 articles about 3-O-ethynyl-1,2-O-isopropylidene-5-O-trityl-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:

Trichloroethylene (79-01-6) + 1,2-O-isopropylidene-5-O-trityl-α-D-xylofuranose (20590-53-8) → 3-O-ethynyl-1,2-O-isopropylidene-5-O-trityl-α-D-xylofuranose (218146-76-0)

Guidance literature:

Multistep reaction;

DOI:10.1016/S0040-4020(98)00857-6

Reference yield:

3-O-ethynyl-1,2-O-isopropylidene-5-O-trityl-α-D-xylofuranose (218146-76-0) → (3'R,4'R)-5-deoxy-1,2-O-isopropylidene-3-O:5-C-[3'-(α-hydroxy-p-nitrobenzyl)-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 / 1 h / -20 - 20 °C

2.1: 99 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: 65 percent / formic acid / diethyl ether / 0.25 h / 20 °C

6.1: 80 percent

7.1: 73 percent / tetrabutylammonium bromide; K₂CO₃ / acetonitrile / Heating

8.1: 53 percent / lithium diisopropylamide / tetrahydrofuran / 1.5 h / -75 °C

With quinoline; n-butyllithium; formic acid; tetrabutylammomium bromide; hydrogen; sodium carbonate; potassium carbonate; sodium bis(2-methoxyethoxy)aluminium dihydride; lithium diisopropyl amide; 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: Alkylation;

DOI:10.1016/S0040-4020(98)00857-6

Reference yield:

3-O-ethynyl-1,2-O-isopropylidene-5-O-trityl-α-D-xylofuranose (218146-76-0) → (3'R,4'R)-5-deoxy-1,2-O-isopropylidene-3-O:5-C-[3'-(α-hydroxybenzyl)-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: 55 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

upstream raw materials:

Trichloroethylene

1,2-O-isopropylidene-5-O-trityl-α-D-xylofuranose

Downstream raw materials:

1,2-O-isopropylidene-3-O-(2'-trimethylsilylethynyl)-5-O-trityl-α-D-xylofuranose

3-O-(2'-t-butyldimethylsilylethynyl)-1,2-O-isopropylidene-5-O-trityl-α-D-xylofuranose

3-O-(2'-dimethylphenylsilylethynyl)-1,2-O-isopropylidene-5-O-trityl-α-D-xylofuranose

(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