(((4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)methoxy)(tert-butyl)diphenylsilane

Base Information

• Chemical Name: (((4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)methoxy)(tert-butyl)diphenylsilane
• CAS No.: 170897-60-6
• Molecular Formula: C₂₄H₃₂O₃Si
• Molecular Weight: 396.602
• Mol file: 170897-60-6.mol

Synonyms:(((4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)methoxy)(tert-butyl)diphenylsilane

Chemical Property of (((4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)methoxy)(tert-butyl)diphenylsilane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (((4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)methoxy)(tert-butyl)diphenylsilane

There total 5 articles about (((4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)methoxy)(tert-butyl)diphenylsilane 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%

Methyltriphenylphosphonium bromide (1779-49-3) + 4-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-L-threose (101331-92-4) → (((4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)methoxy)(tert-butyl)diphenylsilane (170897-60-6)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 10h;

DOI:10.1016/S0040-4039(00)60065-5

Reference yield:

methyl-triphenylphosphonium iodide (2065-66-9) + 4-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-L-threose (101331-92-4) → (((4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)methoxy)(tert-butyl)diphenylsilane (170897-60-6)

Guidance literature:

methyl-triphenylphosphonium iodide; With n-butyllithium; In tetrahydrofuran; at -84 ℃;

4-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-L-threose; In tetrahydrofuran; at -84 - 0 ℃;

DOI:10.1002/jccs.201190054

Reference yield:

2,3-O-isopropylidene-L-threitol (50622-09-8) → (((4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)methoxy)(tert-butyl)diphenylsilane (170897-60-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 91 percent / NaH / 1,2-dimethoxy-ethane / 3 h / -20 °C

2: 1) (COCl)2, DMSO, 2) Et₃N / 1) CH₂Cl₂, -78 deg C, 1 h

3: 92 percent / n-BuLi / tetrahydrofuran / 10 h / -78 °C

With n-butyllithium; oxalyl dichloride; sodium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; 1,2-dimethoxyethane;

DOI:10.1016/S0040-4039(00)60065-5

upstream raw materials:

Methyltriphenylphosphonium bromide

4-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-L-threose

2,3-O-isopropylidene-L-threitol

4-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-L-threitol

Downstream raw materials:

(4S,5S)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-5-vinyl-[1,3]dioxolan-2-one

C₃₀H₄₂O₅Si