(3R,S)-1-(5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-1-deoxy-β-D-ribofuranos-1-yl)pent-4-yn-3-ol

Base Information

• Chemical Name: (3R,S)-1-(5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-1-deoxy-β-D-ribofuranos-1-yl)pent-4-yn-3-ol
• CAS No.: 1352789-39-9
• Molecular Formula: C₂₉H₃₈O₅Si
• Molecular Weight: 494.703
• Mol file: 1352789-39-9.mol

Synonyms:(3R,S)-1-(5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-1-deoxy-β-D-ribofuranos-1-yl)pent-4-yn-3-ol

Chemical Property of (3R,S)-1-(5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-1-deoxy-β-D-ribofuranos-1-yl)pent-4-yn-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,S)-1-(5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-1-deoxy-β-D-ribofuranos-1-yl)pent-4-yn-3-ol

There total 7 articles about (3R,S)-1-(5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-1-deoxy-β-D-ribofuranos-1-yl)pent-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: 83.0%

3-(5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-1-deoxy-β-D-ribofuranosyl-1-yl)propanal (1352789-20-8) + acetylenemagnesium bromide (4301-14-8) → (3R,S)-1-(5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-1-deoxy-β-D-ribofuranos-1-yl)pent-4-yn-3-ol (1352789-39-9)

Guidance literature:

In tetrahydrofuran; at 20 ℃; for 4h;

DOI:10.1055/s-0030-1260200

Reference yield:

(1S,5R,6R,8S)-8-allyl-3,3-dimethyl-6-hydroxymethyl-2,4,7-trioxabicyclo[3.3.0]octane → (3R,S)-1-(5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-1-deoxy-β-D-ribofuranos-1-yl)pent-4-yn-3-ol (1352789-39-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: pyridine / 12 h / 0 - 20 °C

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

2.2: 1.5 h / 0 - 20 °C

3.1: oxalyl dichloride; dimethyl sulfoxide; triethylamine / dichloromethane / 1.25 h / -72 - 20 °C / Inert atmosphere

4.1: tetrahydrofuran / 4 h / 20 °C

With pyridine; borane-THF; oxalyl dichloride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; 3.1: Swern oxidation;

DOI:10.1055/s-0030-1260200

Reference yield:

3-(5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-β-D-ribofuranosyl)prop-1-ene (82921-68-4) → (3R,S)-1-(5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-1-deoxy-β-D-ribofuranos-1-yl)pent-4-yn-3-ol (1352789-39-9)

Guidance literature:

Multi-step reaction with 3 steps

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

1.2: 1.5 h / 0 - 20 °C

2.1: oxalyl dichloride; dimethyl sulfoxide; triethylamine / dichloromethane / 1.25 h / -72 - 20 °C / Inert atmosphere

3.1: tetrahydrofuran / 4 h / 20 °C

With borane-THF; oxalyl dichloride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; 2.1: Swern oxidation;

DOI:10.1055/s-0030-1260200

upstream raw materials:

3-(5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-β-D-ribofuranosyl)prop-1-ene

3-(5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-1-deoxy-β-D-ribofuranos-1-yl)propan-1-ol

3-(5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-1-deoxy-β-D-ribofuranosyl-1-yl)propanal

acetylenemagnesium bromide

Downstream raw materials:

1-(5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-1-deoxy-β-D-ribofuranos-1-yl)pent-4-yn-3-one

4-[2-(5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-1-deoxy-β-D-ribofuranos-1-yl)ethyl]-2-methylpyrimidine

4-[2-(5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-1-deoxy-β-D-ribofuranos-1-yl)ethyl]-2-phenylpyrimidine

4-[2-(5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-1-deoxy-β-D-ribofuranos-1-yl)ethyl]-2-methylthiopyrimidine