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

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-ol
• CAS No.: 1352789-47-9
• Molecular Formula: C₂₈H₄₆O₅Si₂
• Molecular Weight: 518.841
• Mol file: 1352789-47-9.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-ol

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-ol

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-ol

There total 6 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-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: 66.0%

3-[3,5-O-(1,1,3,3-tetraisopropyldisiloxan-1,3-diyl)-1,2-dideoxy-β-D-ribofuranos-1-yl]propanal (1352789-37-7) + lithium phenylacetylide (4440-01-1) → (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)

Guidance literature:

In tetrahydrofuran; at 20 ℃; for 3h;

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-ol (1352789-47-9)

Guidance literature:

Multi-step reaction with 5 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

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

DOI:10.1055/s-0030-1260200

Reference yield:

3-[2-deoxy-3,5-O-(tetraisopropyldisiloxane-1,3-diyl)-β-D-arabinofuranosyl]prop-1-ene (1174314-89-6) → (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)

Guidance literature:

Multi-step reaction with 3 steps

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

1.2: 0 - 20 °C

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

3.1: tetrahydrofuran / 3 h / 20 °C

With borane-THF; Dess-Martin periodane; In tetrahydrofuran; dichloromethane; 2.1: 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-[2-deoxy-3,5-O-(tetraisopropyldisiloxane-1,3-diyl)-β-D-arabinofuranosyl]prop-1-ene

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

lithium phenylacetylide

Downstream raw materials:

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

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