tert-butyldiphenyl ((S)-1-((4R,4'R,5S)-2,2,2',2'-tetramethyl-4,4'-bi(1,3-dioxolan)-5-yl)allyloxy)silane

Base Information

• Chemical Name: tert-butyldiphenyl ((S)-1-((4R,4'R,5S)-2,2,2',2'-tetramethyl-4,4'-bi(1,3-dioxolan)-5-yl)allyloxy)silane
• CAS No.: 1384962-76-8
• Molecular Formula: C₂₉H₄₀O₅Si
• Molecular Weight: 496.719
• Mol file: 1384962-76-8.mol

Synonyms:tert-butyldiphenyl ((S)-1-((4R,4'R,5S)-2,2,2',2'-tetramethyl-4,4'-bi(1,3-dioxolan)-5-yl)allyloxy)silane

Chemical Property of tert-butyldiphenyl ((S)-1-((4R,4'R,5S)-2,2,2',2'-tetramethyl-4,4'-bi(1,3-dioxolan)-5-yl)allyloxy)silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyldiphenyl ((S)-1-((4R,4'R,5S)-2,2,2',2'-tetramethyl-4,4'-bi(1,3-dioxolan)-5-yl)allyloxy)silane

There total 4 articles about tert-butyldiphenyl ((S)-1-((4R,4'R,5S)-2,2,2',2'-tetramethyl-4,4'-bi(1,3-dioxolan)-5-yl)allyloxy)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: 92.0%

(S)-1-((4R,4'R,5R)-2,2,2',2'-tetramethyl-4,4'-bi(1,3-dioxolan)-5-yl)prop-2-en-1-ol (13035-59-1,13035-92-2,22144-63-4,22144-64-5) + tert-butylchlorodiphenylsilane (58479-61-1) → tert-butyldiphenyl ((S)-1-((4R,4'R,5S)-2,2,2',2'-tetramethyl-4,4'-bi(1,3-dioxolan)-5-yl)allyloxy)silane (1384962-76-8)

Guidance literature:

With 1H-imidazole; dmap; In dichloromethane; at 0 - 20 ℃; for 6h;

DOI:10.1016/j.tetlet.2012.05.099

Reference yield:

1,2-anhydro-3,4:5,6-di-O-isopropylidene-D-glucitol (85325-93-5,105454-09-9,105454-10-2) → tert-butyldiphenyl ((S)-1-((4R,4'R,5S)-2,2,2',2'-tetramethyl-4,4'-bi(1,3-dioxolan)-5-yl)allyloxy)silane (1384962-76-8)

Guidance literature:

Multi-step reaction with 2 steps

1: n-butyllithium / tetrahydrofuran / 2 h / -10 °C

2: 1H-imidazole; dmap / dichloromethane / 6 h / 0 - 20 °C

With 1H-imidazole; dmap; n-butyllithium; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.tetlet.2012.05.099

Reference yield:

6-O-benzoyl-1,2:3,4-di-O-isopropylidene-D-mannitol (290836-45-2) → tert-butyldiphenyl ((S)-1-((4R,4'R,5S)-2,2,2',2'-tetramethyl-4,4'-bi(1,3-dioxolan)-5-yl)allyloxy)silane (1384962-76-8)

Guidance literature:

Multi-step reaction with 4 steps

1: triethylamine / dichloromethane / -80 - -20 °C

2: potassium carbonate / methanol / 0 - 20 °C

3: n-butyllithium / tetrahydrofuran / 2 h / -10 °C

4: 1H-imidazole; dmap / dichloromethane / 6 h / 0 - 20 °C

With 1H-imidazole; dmap; n-butyllithium; potassium carbonate; triethylamine; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1016/j.tetlet.2012.05.099

upstream raw materials:

1,2-anhydro-3,4:5,6-di-O-isopropylidene-D-glucitol

(S)-1-((4R,4'R,5R)-2,2,2',2'-tetramethyl-4,4'-bi(1,3-dioxolan)-5-yl)prop-2-en-1-ol

tert-butylchlorodiphenylsilane

6-O-benzoyl-1,2:3,4-di-O-isopropylidene-D-mannitol

Downstream raw materials:

(R)-1-((4R,5S)-5-((S)-1-(tert-butyldiphenylsilyloxy)allyl)-2,2-dimethyl-1,3-dioxolan-4-yl)ethane-1,2-diol

C₃₃H₄₂O₇SSi

(-)-anamarine