(3R,S)-1-[3,5-O-(tetraisopropyldisiloxane-1,3-diyl)-1,2-dideoxy-β-D-ribofuranos-1-yl]-5-phenylpent-4-yn-3-one

Base Information

• Chemical Name: (3R,S)-1-[3,5-O-(tetraisopropyldisiloxane-1,3-diyl)-1,2-dideoxy-β-D-ribofuranos-1-yl]-5-phenylpent-4-yn-3-one
• CAS No.: 1352789-49-1
• Molecular Formula: C₂₈H₄₄O₅Si₂
• Molecular Weight: 516.825
• Mol file: 1352789-49-1.mol

Synonyms:(3R,S)-1-[3,5-O-(tetraisopropyldisiloxane-1,3-diyl)-1,2-dideoxy-β-D-ribofuranos-1-yl]-5-phenylpent-4-yn-3-one

Chemical Property of (3R,S)-1-[3,5-O-(tetraisopropyldisiloxane-1,3-diyl)-1,2-dideoxy-β-D-ribofuranos-1-yl]-5-phenylpent-4-yn-3-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,S)-1-[3,5-O-(tetraisopropyldisiloxane-1,3-diyl)-1,2-dideoxy-β-D-ribofuranos-1-yl]-5-phenylpent-4-yn-3-one

There total 7 articles about (3R,S)-1-[3,5-O-(tetraisopropyldisiloxane-1,3-diyl)-1,2-dideoxy-β-D-ribofuranos-1-yl]-5-phenylpent-4-yn-3-one 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: 60.0%

(3R,S)-1-[3,5-O-(tetraisopropyldisiloxane-1,3-diyl)-1,2-dideoxy-β-D-ribofuranos-1-yl]-5-phenylpent-4-yn-3-ol (1352789-47-9) → (3R,S)-1-[3,5-O-(tetraisopropyldisiloxane-1,3-diyl)-1,2-dideoxy-β-D-ribofuranos-1-yl]-5-phenylpent-4-yn-3-one (1352789-49-1)

Guidance literature:

With sodium hydrogencarbonate; Dess-Martin periodane; In dichloromethane; at 0 - 20 ℃; for 2h; Molecular sieve; Inert atmosphere;

DOI:10.1055/s-0030-1260200

Reference yield:

3-[3,5-O-(1,1,3,3-tetraisopropyldisiloxan-1,3-diyl)-1,2-dideoxy-β-D-ribofuranos-1-yl]propanal (1352789-37-7) → (3R,S)-1-[3,5-O-(tetraisopropyldisiloxane-1,3-diyl)-1,2-dideoxy-β-D-ribofuranos-1-yl]-5-phenylpent-4-yn-3-one (1352789-49-1)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrahydrofuran / 3 h / 20 °C

2: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 2 h / 0 - 20 °C / Molecular sieve; Inert atmosphere

With sodium hydrogencarbonate; Dess-Martin periodane; In tetrahydrofuran; dichloromethane; 2: Dess-Martin oxidation;

DOI:10.1055/s-0030-1260200

Reference yield:

3-[3,5-O-(tetraisopropyldisiloxane-1,3-diyl)-β-D-ribofuranosyl]prop-1-ene (1174314-87-4) → (3R,S)-1-[3,5-O-(tetraisopropyldisiloxane-1,3-diyl)-1,2-dideoxy-β-D-ribofuranos-1-yl]-5-phenylpent-4-yn-3-one (1352789-49-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 1H-imidazole; iodine; triphenylphosphine / toluene

2.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / 10 h / Reflux

3.1: borane-THF / tetrahydrofuran / 3 h / 0 °C

3.2: 0 - 20 °C

4.1: Dess-Martin periodane / dichloromethane / 5 h / 20 °C / Inert atmosphere

5.1: tetrahydrofuran / 3 h / 20 °C

6.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 2 h / 0 - 20 °C / Molecular sieve; Inert atmosphere

With 1H-imidazole; borane-THF; 2,2'-azobis(isobutyronitrile); iodine; tri-n-butyl-tin hydride; sodium hydrogencarbonate; Dess-Martin periodane; triphenylphosphine; In tetrahydrofuran; dichloromethane; toluene; 4.1: Dess-Martin oxidation / 6.1: Dess-Martin oxidation;

DOI:10.1055/s-0030-1260200

upstream raw materials:

3-[3,5-O-(tetraisopropyldisiloxane-1,3-diyl)-β-D-ribofuranosyl]prop-1-ene

3-[3,5-O-(1,1,3,3-tetraisopropyldisiloxan-1,3-diyl)-1,2-dideoxy-β-D-ribofuranos-1-yl]propanal

(3R,S)-1-[3,5-O-(tetraisopropyldisiloxane-1,3-diyl)-1,2-dideoxy-β-D-ribofuranos-1-yl]-5-phenylpent-4-yn-3-ol

1,5-di-O-acetyl-2,3-O-isopropylidene-β-D-ribofuranose

Downstream raw materials:

4-[2-[3,5-O-(tetraisopropyldisiloxan-1,3-diyl)-1,2-dideoxy-β-D-ribofuranos-1-yl]ethyl]-2-methyl-6-phenylpyrimidine