1-[2,2-dimethyl-5-(1-(trityloxymethyl)vinyl)-[1,3]dioxolan-4-yl]prop-2-en-1-ol

Base Information

• Chemical Name: 1-[2,2-dimethyl-5-(1-(trityloxymethyl)vinyl)-[1,3]dioxolan-4-yl]prop-2-en-1-ol
• CAS No.: 934816-33-8
• Molecular Formula: C₃₀H₃₂O₄
• Molecular Weight: 456.582
• Mol file: 934816-33-8.mol

Synonyms:1-[2,2-dimethyl-5-(1-(trityloxymethyl)vinyl)-[1,3]dioxolan-4-yl]prop-2-en-1-ol

Chemical Property of 1-[2,2-dimethyl-5-(1-(trityloxymethyl)vinyl)-[1,3]dioxolan-4-yl]prop-2-en-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[2,2-dimethyl-5-(1-(trityloxymethyl)vinyl)-[1,3]dioxolan-4-yl]prop-2-en-1-ol

There total 5 articles about 1-[2,2-dimethyl-5-(1-(trityloxymethyl)vinyl)-[1,3]dioxolan-4-yl]prop-2-en-1-ol 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: 98.0%

tert-butyl-{1-[2,2-dimethyl-5-(1-(trityloxymethyl)vinyl)-[1,3]dioxolan-4-yl]allyloxy}dimethylsilane (934816-32-7) → 1-[2,2-dimethyl-5-(1-(trityloxymethyl)vinyl)-[1,3]dioxolan-4-yl]prop-2-en-1-ol (934816-33-8)

Guidance literature:

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

DOI:10.1021/jm0509750

Reference yield:

1-{5-[1-((tert-butyldimethylsilanyl)oxyl)allyl]-2,2-dimethyl[1,3]dioxolan-4-yl}-2-(trityloxy)ethanone (934816-31-6) → 1-[2,2-dimethyl-5-(1-(trityloxymethyl)vinyl)-[1,3]dioxolan-4-yl]prop-2-en-1-ol (934816-33-8)

Guidance literature:

Multi-step reaction with 2 steps

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

1.2: 95 percent / tetrahydrofuran; hexane / 12 h / 20 °C

2.1: 98 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C

With n-butyllithium; tetrabutyl ammonium fluoride; In tetrahydrofuran; hexane; 1.2: Wittig reaction;

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) → 1-[2,2-dimethyl-5-(1-(trityloxymethyl)vinyl)-[1,3]dioxolan-4-yl]prop-2-en-1-ol (934816-33-8)

Guidance literature:

Multi-step reaction with 3 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

3.1: 98 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C

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

DOI:10.1021/jm0509750

upstream raw materials:

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

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

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:

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

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

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