[5,7-bis-benzyloxy-2-(3,4,5-tris-benzyloxy-phenyl)-chroman-3-yloxy]-tert-butyl-dimethyl-silane

Base Information

• Chemical Name: [5,7-bis-benzyloxy-2-(3,4,5-tris-benzyloxy-phenyl)-chroman-3-yloxy]-tert-butyl-dimethyl-silane
• CAS No.: 915954-71-1
• Molecular Formula: C₅₆H₅₈O₇Si
• Molecular Weight: 871.158
• Mol file: 915954-71-1.mol

Synonyms:[5,7-bis-benzyloxy-2-(3,4,5-tris-benzyloxy-phenyl)-chroman-3-yloxy]-tert-butyl-dimethyl-silane

Chemical Property of [5,7-bis-benzyloxy-2-(3,4,5-tris-benzyloxy-phenyl)-chroman-3-yloxy]-tert-butyl-dimethyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [5,7-bis-benzyloxy-2-(3,4,5-tris-benzyloxy-phenyl)-chroman-3-yloxy]-tert-butyl-dimethyl-silane

There total 10 articles about [5,7-bis-benzyloxy-2-(3,4,5-tris-benzyloxy-phenyl)-chroman-3-yloxy]-tert-butyl-dimethyl-silane 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: 96.4%

[2-(3,5-bis-benzyloxy-2-iodo-phenoxy)-1-bromomethyl-2-(3,4,5-tris-benzyloxy-phenyl)-ethoxy]-tert-butyl-dimethyl-silane (915954-70-0) → [5,7-bis-benzyloxy-2-(3,4,5-tris-benzyloxy-phenyl)-chroman-3-yloxy]-tert-butyl-dimethyl-silane (915954-71-1)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; phenyllithium; phenylmagnesium bromide; In various solvents; at -78 ℃; for 1h;

DOI:10.1246/cl.2006.1006

Reference yield: 13.0%

[2-(3,5-bis-benzyloxy-2-iodo-phenoxy)-1-bromomethyl-2-(3,4,5-tris-benzyloxy-phenyl)-ethoxy]-tert-butyl-dimethyl-silane (915954-70-0) → [2-(3,5-bis-benzyloxy-phenoxy)-1-methyl-2-(3,4,5-tris-benzyloxy-phenyl)-ethoxy]-tert-butyl-dimethyl-silane + [5,7-bis-benzyloxy-2-(3,4,5-tris-benzyloxy-phenyl)-chroman-3-yloxy]-tert-butyl-dimethyl-silane (915954-71-1)

Guidance literature:

[2-(3,5-bis-benzyloxy-2-iodo-phenoxy)-1-bromomethyl-2-(3,4,5-tris-benzyloxy-phenyl)-ethoxy]-tert-butyl-dimethyl-silane; With tert.-butyl lithium; In tetrahydrofuran; at -78 ℃;

With deuteromethanol; In tetrahydrofuran; at -78 - 0 ℃;

DOI:10.1246/cl.2006.1006

Reference yield:

(E)-methyl 3-(3,4,5-tris(benzyloxy)phenyl)acrylate → [5,7-bis-benzyloxy-2-(3,4,5-tris-benzyloxy-phenyl)-chroman-3-yloxy]-tert-butyl-dimethyl-silane (915954-71-1)

Guidance literature:

Multi-step reaction with 8 steps

1.1: diisobutylaluminum hydride / tetrahydrofuran; hexane / 0.5 h / -78 °C

1.2: 96 percent / aq. Rochelle's salt / tetrahydrofuran; hexane; methanol / 3 h / 0 °C

2.1: 92 percent / K₃Fe(CN)6; MeSO₂NH₂; K₂CO₃ / (DHQD)2-PHAL; K₂OsO₂(OH)2 / 2-methyl-propan-2-ol; H₂O / 40.5 h / 0 °C

3.1: 89 percent / pyridine / 18 h / 0 °C

4.1: 90 percent / K₂CO₃ / methanol; dioxane / 1.5 h / 0 °C

5.1: 93 percent / TMAD; n-Bu₃P / toluene / 10 h / 0 °C

6.1: 93 percent / Li₂NiBr₄ / tetrahydrofuran / 8 h / 0 °C

7.1: 93 percent / 2,6-di-t-butylpyridine / CH₂Cl₂ / 1 h / 0 °C

8.1: tBuLi / tetrahydrofuran / -78 °C

8.2: 53 percent / CH₃OD / tetrahydrofuran / -78 - 0 °C

With pyridine; 2,6-di-tert-butyl-pyridine; tributylphosphine; methanesulfonamide; dilithium tetrabromonickelate(II); diamide; tert.-butyl lithium; diisobutylaluminium hydride; potassium carbonate; potassium hexacyanoferrate(III); K₂OsO₂(OH)2; 1,4-bis(9-O-dihydroquinidine)phthalazine; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; water; toluene; tert-butyl alcohol;

DOI:10.1246/cl.2006.1006

upstream raw materials:

[2-(3,5-bis-benzyloxy-2-iodo-phenoxy)-1-bromomethyl-2-(3,4,5-tris-benzyloxy-phenyl)-ethoxy]-tert-butyl-dimethyl-silane

oxiranyl-(3,4,5-tris-benzyloxy-phenyl)-methanol

1-(3,4,5-tris-benzyloxy-phenyl)-propane-1,2,3-triol

2,4,6-triisopropyl-benzenesulfonic acid 2,3-dihydroxy-3-(3,4,5-tris-benzyloxy-phenyl)-propyl ester

Downstream raw materials:

(-)-gallocatechin

(+)-(2S,3R)-trans-5,7-bis(benzyloxy)-2-[3,4,5-tris(benzyloxy)phenyl]chroman-3-ol