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

Base Information

• Chemical Name: 1-{5-[1-((tert-butyldimethylsilanyl)oxyl)allyl]-2,2-dimethyl[1,3]dioxolan-4-yl}-2-(trityloxy)ethanol
• CAS No.: 934816-30-5
• Molecular Formula: C₃₅H₄₆O₅Si
• Molecular Weight: 574.833

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

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

Chemical Property:

Purity/Quality:

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

There total 2 articles about 1-{5-[1-((tert-butyldimethylsilanyl)oxyl)allyl]-2,2-dimethyl[1,3]dioxolan-4-yl}-2-(trityloxy)ethanol 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: 82.0%

tert-butyldimethylsilyl chloride (18162-48-6) + 1-[5-(1-hydroxy-2-trityloxyethyl)-2,2-dimethyl[1,3]dioxolan-4-yl]prop-2-en-1-ol (54187-70-1) → 1-{5-[1-((tert-butyldimethylsilanyl)oxyl)allyl]-2,2-dimethyl[1,3]dioxolan-4-yl}-2-(trityloxy)ethanol (934816-30-5)

Guidance literature:

With 1H-imidazole; In dichloromethane; N,N-dimethyl-formamide; at 20 ℃; for 24h;

DOI:10.1021/jm0509750

Reference yield:

2,3-O-isopropylidene-5-O-trityl-D-ribofuranose (54503-64-9,54503-65-0) → 1-{5-[1-((tert-butyldimethylsilanyl)oxyl)allyl]-2,2-dimethyl[1,3]dioxolan-4-yl}-2-(trityloxy)ethanol (934816-30-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 25.29 g / tetrahydrofuran / 7 h / -78 - 20 °C

2: 82 percent / imidazole / CH₂Cl₂; dimethylformamide / 24 h / 20 °C

With 1H-imidazole; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm0509750

Reference yield: 95.0%

1-{5-[1-((tert-butyldimethylsilanyl)oxyl)allyl]-2,2-dimethyl[1,3]dioxolan-4-yl}-2-(trityloxy)ethanol (934816-30-5) → 1-{5-[1-((tert-butyldimethylsilanyl)oxyl)allyl]-2,2-dimethyl[1,3]dioxolan-4-yl}-2-(trityloxy)ethanone (934816-31-6)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -60 - 20 ℃;

DOI:10.1021/jm0509750

upstream raw materials:

tert-butyldimethylsilyl chloride

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

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

Downstream raw materials:

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

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

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