4-[4,6-di-O-(tert-butyldimethylsilyl)-2,3-dideoxy-β-D-erythro-hex-2-enopyranosyl]biphenyl

Base Information

• Chemical Name: 4-[4,6-di-O-(tert-butyldimethylsilyl)-2,3-dideoxy-β-D-erythro-hex-2-enopyranosyl]biphenyl
• CAS No.: 368452-20-4
• Molecular Formula: C₃₀H₄₆O₃Si₂
• Molecular Weight: 510.864
• Mol file: 368452-20-4.mol

Synonyms:4-[4,6-di-O-(tert-butyldimethylsilyl)-2,3-dideoxy-β-D-erythro-hex-2-enopyranosyl]biphenyl

Chemical Property of 4-[4,6-di-O-(tert-butyldimethylsilyl)-2,3-dideoxy-β-D-erythro-hex-2-enopyranosyl]biphenyl

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-[4,6-di-O-(tert-butyldimethylsilyl)-2,3-dideoxy-β-D-erythro-hex-2-enopyranosyl]biphenyl

There total 1 articles about 4-[4,6-di-O-(tert-butyldimethylsilyl)-2,3-dideoxy-β-D-erythro-hex-2-enopyranosyl]biphenyl 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: 71.0%

4-biphenylylmagnesium bromide (3315-91-1) + p-tert-butylphenyl 4,6-di-O-tert-butyl(dimethyl)silyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside (201232-73-7) → 4-[4,6-di-O-(tert-butyldimethylsilyl)-2,3-dideoxy-β-D-erythro-hex-2-enopyranosyl]biphenyl (368452-20-4)

Guidance literature:

1,2-bis(diphenylphosphino)ethane nickel(II) chloride; In tetrahydrofuran; for 24h;

DOI:10.1081/CAR-100104867

Reference yield: 90.0%

4-[4,6-di-O-(tert-butyldimethylsilyl)-2,3-dideoxy-β-D-erythro-hex-2-enopyranosyl]biphenyl (368452-20-4) → 4-(2,3-dideoxy-β-D-erythro-hex-2-enopyranosyl)biphenyl (368452-26-0)

Guidance literature:

With tetrabutyl-ammonium chloride; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1081/CAR-100104867

Reference yield:

4-[4,6-di-O-(tert-butyldimethylsilyl)-2,3-dideoxy-β-D-erythro-hex-2-enopyranosyl]biphenyl (368452-20-4) → (1S,3R,6R,8R)-8-biphenyl-3-(4'-methyloxyphenyl)-2,4,7-trioxabicyclo[4.4.0]decane

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / tetrabutylammonium chloride trihydrate / tetrahydrofuran / 2 h / 20 °C

2: 90 percent / H₂ / [Rh(COD)(dppb)]ClO₄ / ethanol / 24 h / 20 °C / 760 Torr

3: 32 percent / p-TsOH*H₂O / dimethylformamide / 60 °C / 22.5 Torr

With tetrabutyl-ammonium chloride; hydrogen; toluene-4-sulfonic acid; [Rh(COD)(1,4-bis(diphenylphosphino)butane)]ClO₄; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide;

DOI:10.1081/CAR-100104867

upstream raw materials:

4-biphenylylmagnesium bromide

p-tert-butylphenyl 4,6-di-O-tert-butyl(dimethyl)silyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside

Downstream raw materials:

4-(2,3-dideoxy-β-D-erythro-hex-2-enopyranosyl)biphenyl

4-(2,3-dideoxy-β-D-erythro-hexanopyranosyl)biphenyl