2-O-(2,4-dimethoxybenzoyl)-3,5-O-(1,1,3,3-tetraisopropyldiloxane-1,3-diyl)-1-O-acetyl-4-thio-D-fibofuranose

Base Information

• Chemical Name: 2-O-(2,4-dimethoxybenzoyl)-3,5-O-(1,1,3,3-tetraisopropyldiloxane-1,3-diyl)-1-O-acetyl-4-thio-D-fibofuranose
• CAS No.: 291758-26-4
• Molecular Formula: C₂₈H₄₆O₉SSi₂
• Molecular Weight: 614.905
• Mol file: 291758-26-4.mol

Synonyms:2-O-(2,4-dimethoxybenzoyl)-3,5-O-(1,1,3,3-tetraisopropyldiloxane-1,3-diyl)-1-O-acetyl-4-thio-D-fibofuranose

Chemical Property of 2-O-(2,4-dimethoxybenzoyl)-3,5-O-(1,1,3,3-tetraisopropyldiloxane-1,3-diyl)-1-O-acetyl-4-thio-D-fibofuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-O-(2,4-dimethoxybenzoyl)-3,5-O-(1,1,3,3-tetraisopropyldiloxane-1,3-diyl)-1-O-acetyl-4-thio-D-fibofuranose

There total 1 articles about 2-O-(2,4-dimethoxybenzoyl)-3,5-O-(1,1,3,3-tetraisopropyldiloxane-1,3-diyl)-1-O-acetyl-4-thio-D-fibofuranose 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: 41.0%

acetic anhydride (108-24-7) + 1,4-anhydro-2-O-(2,4-dimethoxybenzoyl)-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-sulfinyl-D-ribitol (869347-03-5) → 2-O-(2,4-dimethoxybenzoyl)-3,5-O-(1,1,3,3-tetraisopropyldiloxane-1,3-diyl)-1-O-acetyl-4-thio-D-fibofuranose (291758-26-4)

Guidance literature:

at 110 ℃; for 6h;

DOI:10.1021/ja000541o

Reference yield:

2-O-(2,4-dimethoxybenzoyl)-3,5-O-(1,1,3,3-tetraisopropyldiloxane-1,3-diyl)-1-O-acetyl-4-thio-D-fibofuranose (291758-26-4) → 2,4-Dimethoxy-benzoic acid (2R,3R,4S,5R)-4-hydroxy-5-hydroxymethyl-2-(4-hydroxy-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-thiophen-3-yl ester

Guidance literature:

Multi-step reaction with 2 steps

1: N,O-bis(trimethylsilyl)acetamide; TMSOTf / acetonitrile

2: ammonium fluoride / methanol / 12 h / Heating

With N,O-bis-(trimethylsilyl)-acetamide; ammonium fluoride; trimethylsilyl trifluoromethanesulfonate; In methanol; acetonitrile; 1: Glycosylation / 2: Desilylation;

DOI:10.1021/ja000541o

Reference yield:

uracil (66-22-8,144104-68-7,18324-22-6,27072-01-1,2920-92-5,51953-19-6) + 2-O-(2,4-dimethoxybenzoyl)-3,5-O-(1,1,3,3-tetraisopropyldiloxane-1,3-diyl)-1-O-acetyl-4-thio-D-fibofuranose (291758-26-4) → 1-[2-O-(2,4-dimethoxybenzoyl)-2,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-thio-β-D-ribofuranosyl]uracil (291758-14-0)

Guidance literature:

With N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; In acetonitrile;

DOI:10.1021/ja000541o

upstream raw materials:

acetic anhydride

1,4-anhydro-2-O-(2,4-dimethoxybenzoyl)-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-sulfinyl-D-ribitol

Downstream raw materials:

1-[2-O-(2,4-dimethoxybenzoyl)-2,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-thio-β-D-ribofuranosyl]uracil

1-(4-thio-β-D-ribofuransoyl)uracil