tert-butyl-{1-[2,2-dimethyl-5-(1-(trityloxymethyl)vinyl)-[1,3]dioxolan-4-yl]allyloxy}dimethylsilane

Base Information

• Chemical Name: tert-butyl-{1-[2,2-dimethyl-5-(1-(trityloxymethyl)vinyl)-[1,3]dioxolan-4-yl]allyloxy}dimethylsilane
• CAS No.: 934816-32-7
• Molecular Formula: C₃₆H₄₆O₄Si
• Molecular Weight: 570.844
• Mol file: 934816-32-7.mol

Synonyms:tert-butyl-{1-[2,2-dimethyl-5-(1-(trityloxymethyl)vinyl)-[1,3]dioxolan-4-yl]allyloxy}dimethylsilane

Chemical Property of tert-butyl-{1-[2,2-dimethyl-5-(1-(trityloxymethyl)vinyl)-[1,3]dioxolan-4-yl]allyloxy}dimethylsilane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl-{1-[2,2-dimethyl-5-(1-(trityloxymethyl)vinyl)-[1,3]dioxolan-4-yl]allyloxy}dimethylsilane

There total 4 articles about tert-butyl-{1-[2,2-dimethyl-5-(1-(trityloxymethyl)vinyl)-[1,3]dioxolan-4-yl]allyloxy}dimethylsilane 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: 95.0%

1-{5-[1-((tert-butyldimethylsilanyl)oxyl)allyl]-2,2-dimethyl[1,3]dioxolan-4-yl}-2-(trityloxy)ethanone (934816-31-6) + Methyltriphenylphosphonium bromide (1779-49-3) → tert-butyl-{1-[2,2-dimethyl-5-(1-(trityloxymethyl)vinyl)-[1,3]dioxolan-4-yl]allyloxy}dimethylsilane (934816-32-7)

Guidance literature:

Methyltriphenylphosphonium bromide; With n-butyllithium; In tetrahydrofuran; hexane; at 0 ℃; for 0.5h;

1-{5-[1-((tert-butyldimethylsilanyl)oxyl)allyl]-2,2-dimethyl[1,3]dioxolan-4-yl}-2-(trityloxy)ethanone; In tetrahydrofuran; hexane; at 20 ℃; for 12h;

DOI:10.1021/jm0509750

Reference yield:

1-{5-[1-((tert-butyldimethylsilanyl)oxyl)allyl]-2,2-dimethyl[1,3]dioxolan-4-yl}-2-(trityloxy)ethanol (934816-30-5) → tert-butyl-{1-[2,2-dimethyl-5-(1-(trityloxymethyl)vinyl)-[1,3]dioxolan-4-yl]allyloxy}dimethylsilane (934816-32-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 95 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -60 - 20 °C

2.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / 0 °C

2.2: 95 percent / tetrahydrofuran; hexane / 12 h / 20 °C

With n-butyllithium; oxalyl dichloride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; hexane; dichloromethane; 1.1: Swern oxidation / 2.2: Wittig reaction;

DOI:10.1021/jm0509750

Reference yield:

2,3-O-isopropylidene-5-O-trityl-D-ribofuranose (54503-64-9,54503-65-0) → tert-butyl-{1-[2,2-dimethyl-5-(1-(trityloxymethyl)vinyl)-[1,3]dioxolan-4-yl]allyloxy}dimethylsilane (934816-32-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 25.29 g / tetrahydrofuran / 7 h / -78 - 20 °C

2.1: 82 percent / imidazole / CH₂Cl₂; dimethylformamide / 24 h / 20 °C

3.1: 95 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -60 - 20 °C

4.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / 0 °C

4.2: 95 percent / tetrahydrofuran; hexane / 12 h / 20 °C

With 1H-imidazole; n-butyllithium; oxalyl dichloride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; 3.1: Swern oxidation / 4.2: Wittig reaction;

DOI:10.1021/jm0509750

upstream raw materials:

1-{5-[1-((tert-butyldimethylsilanyl)oxyl)allyl]-2,2-dimethyl[1,3]dioxolan-4-yl}-2-(trityloxy)ethanone

Methyltriphenylphosphonium bromide

1-{5-[1-((tert-butyldimethylsilanyl)oxyl)allyl]-2,2-dimethyl[1,3]dioxolan-4-yl}-2-(trityloxy)ethanol

2,3-O-isopropylidene-5-O-trityl-D-ribofuranose

Downstream raw materials:

4-azido-2,2-dimethyl-6-trityloxymethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxole

(1S,2R,3R)-2,3-(isopropylidenedioxy)-4-(trityloxymethyl)-4-cyclopenten-1-yl methanesulfonate

1-(2,2-dimethyl-6-trityloxymethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-yl)-1H-imidazole-4-carboxylic acid amide

1-(2,2-dimethyl-6-trityloxymethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-yl)-1H-1,2,3-triazole-4-carboxylic acid methyl ester