(Z)-1,2-O-isopropylidene-3-O-(2'-trimethylsilyl-vinyl)-5-O-trityl-α-D-xylofuranose

Base Information

• Chemical Name: (Z)-1,2-O-isopropylidene-3-O-(2'-trimethylsilyl-vinyl)-5-O-trityl-α-D-xylofuranose
• CAS No.: 218146-80-6
• Molecular Formula: C₃₂H₃₈O₅Si
• Molecular Weight: 530.736
• Mol file: 218146-80-6.mol

Synonyms:(Z)-1,2-O-isopropylidene-3-O-(2'-trimethylsilyl-vinyl)-5-O-trityl-α-D-xylofuranose

Chemical Property of (Z)-1,2-O-isopropylidene-3-O-(2'-trimethylsilyl-vinyl)-5-O-trityl-α-D-xylofuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-1,2-O-isopropylidene-3-O-(2'-trimethylsilyl-vinyl)-5-O-trityl-α-D-xylofuranose

There total 4 articles about (Z)-1,2-O-isopropylidene-3-O-(2'-trimethylsilyl-vinyl)-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: 99.0%

1,2-O-isopropylidene-3-O-(2'-trimethylsilylethynyl)-5-O-trityl-α-D-xylofuranose (218146-77-1) → (Z)-1,2-O-isopropylidene-3-O-(2'-trimethylsilyl-vinyl)-5-O-trityl-α-D-xylofuranose (218146-80-6)

Guidance literature:

With quinoline; hydrogen; Pd-BaSO₄; In hexane; ethyl acetate; for 4h;

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

Reference yield:

1,2-O-isopropylidene-5-O-trityl-α-D-xylofuranose (20590-53-8) → (Z)-1,2-O-isopropylidene-3-O-(2'-trimethylsilyl-vinyl)-5-O-trityl-α-D-xylofuranose (218146-80-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 74 percent / pyridine; Ac₂O / 3 h / 0 °C

2: toluene / 3 h / 110 °C

With pyridine; acetic anhydride; In toluene;

DOI:10.1080/10426500307948

Reference yield:

3-O-ethynyl-1,2-O-isopropylidene-5-O-trityl-α-D-xylofuranose (218146-76-0) → (Z)-1,2-O-isopropylidene-3-O-(2'-trimethylsilyl-vinyl)-5-O-trityl-α-D-xylofuranose (218146-80-6)

Guidance literature:

Multi-step reaction with 2 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

With quinoline; n-butyllithium; hydrogen; Pd-BaSO₄; In tetrahydrofuran; hexane; ethyl acetate; 1.1: Metallation / 1.2: silylation / 2.1: Catalytic hydrogenation;

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

upstream raw materials:

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

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

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

Downstream raw materials:

(3'S, 4'R)-1,2-O-isopropylidene-3-O-(3'-trimethylsilylazetidin-2'-on-4'-yl)-5-O-trityl-α-D-xylofuranose

(3'S, 4'R)-1,2-O-isopropylidene-3-O-(3'-trimethylsilylazetidin-2'-on-4'-yl)-5-O-tosyl-α-D-xylofuranose