1-{(3S,5S)-2-benzyl-3-[(4S)-2,2-dimethyl-1.3-dioxolan-4-yl]isoxazolidin-5-yl}thymine

Base Information

• Chemical Name: 1-{(3S,5S)-2-benzyl-3-[(4S)-2,2-dimethyl-1.3-dioxolan-4-yl]isoxazolidin-5-yl}thymine
• CAS No.: 287195-03-3
• Molecular Formula: C₂₀H₂₅N₃O₅
• Molecular Weight: 387.436
• Mol file: 287195-03-3.mol

Synonyms:1-{(3S,5S)-2-benzyl-3-[(4S)-2,2-dimethyl-1.3-dioxolan-4-yl]isoxazolidin-5-yl}thymine

Chemical Property of 1-{(3S,5S)-2-benzyl-3-[(4S)-2,2-dimethyl-1.3-dioxolan-4-yl]isoxazolidin-5-yl}thymine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-{(3S,5S)-2-benzyl-3-[(4S)-2,2-dimethyl-1.3-dioxolan-4-yl]isoxazolidin-5-yl}thymine

There total 6 articles about 1-{(3S,5S)-2-benzyl-3-[(4S)-2,2-dimethyl-1.3-dioxolan-4-yl]isoxazolidin-5-yl}thymine 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: 64.0%

N-benzyl-2,3-O-isopropylidene-D-glyceraldehyde nitrone (91190-38-4,111058-38-9,1165677-00-8) + 1-vinylthymine (20245-84-5) → 1-{(3R,5S)-2-benzyl-3-[(1S)-2,2-dimethyl-1.3-dioxolan-4-yl]isoxazolidin-5-yl}thymine (287195-06-6) + 1-{(3S,5R)-2-benzyl-3-[(4S)-2,2-dimethyl-1.3-dioxolan-4-yl]isoxazolidin-5-yl}thymine (287195-02-2) + 1-{(3S,5S)-2-benzyl-3-[(4S)-2,2-dimethyl-1.3-dioxolan-4-yl]isoxazolidin-5-yl}thymine (287195-03-3)

Guidance literature:

In toluene; for 15h; Heating;

DOI:10.1016/S0957-4166(00)00094-X

Reference yield: 60.0%

(3S)-5-acetoxy-2-benzyl-3-[(4S)-2,2-dimethyl-1.3-dioxolan-4-yl]isoxazolidine (320574-51-4) + 2,4-bis(trimethylsiloxy)-5-methylpyrimidine (7288-28-0) → 1-{(3S,5R)-2-benzyl-3-[(4S)-2,2-dimethyl-1.3-dioxolan-4-yl]isoxazolidin-5-yl}thymine (287195-02-2) + 1-{(3S,5S)-2-benzyl-3-[(4S)-2,2-dimethyl-1.3-dioxolan-4-yl]isoxazolidin-5-yl}thymine (287195-03-3)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at 20 ℃; for 4h;

DOI:10.1016/S0957-4166(00)00094-X

Reference yield:

Methyl (3S,4S)-3--4,5-(isopropylidenedioxy)-pentanoate (121614-07-1) → 1-{(3S,5S)-2-benzyl-3-[(4S)-2,2-dimethyl-1.3-dioxolan-4-yl]isoxazolidin-5-yl}thymine (287195-03-3)

Guidance literature:

Multi-step reaction with 5 steps

1: HF; pyridine / 0.5 h / 0 °C

2: NaOMe / methanol / 4 h / 20 °C

3: DIBAH / CH₂Cl₂ / 1 h / -80 °C

4: pyridine / 0.5 h / 0 °C

5: TMSOTf / CH₂Cl₂

With pyridine; trimethylsilyl trifluoromethanesulfonate; hydrogen fluoride; sodium methylate; diisobutylaluminium hydride; In methanol; dichloromethane;

DOI:10.1016/S0040-4039(00)01674-9

upstream raw materials:

N-benzyl-2,3-O-isopropylidene-D-glyceraldehyde nitrone

1-vinylthymine

(3S)-5-acetoxy-2-benzyl-3-[(4S)-2,2-dimethyl-1.3-dioxolan-4-yl]isoxazolidine

2,4-bis(trimethylsiloxy)-5-methylpyrimidine