[4-(6-Amino-2-chloropurin-9-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methyl 4-methylbenzenesulfonate

Base Information

• Chemical Name: [4-(6-Amino-2-chloropurin-9-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methyl 4-methylbenzenesulfonate
• CAS No.: 53458-44-9
• Molecular Formula: C20H22ClN5O6S
• Molecular Weight: 495.944
• NSC Number: 164686
• DSSTox Substance ID: DTXSID90304226
• Mol file: 53458-44-9.mol

Synonyms:NSC164686;53458-44-9;DTXSID90304226;NSC-164686

Chemical Property of [4-(6-Amino-2-chloropurin-9-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methyl 4-methylbenzenesulfonate

Chemical Property:

• Vapor Pressure: 3.9E-17mmHg at 25°C
• Boiling Point: 657°Cat760mmHg
• Flash Point: 351.1°C
• Density: 1.7g/cm³
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 5
• Exact Mass: 495.0979323
• Heavy Atom Count: 33
• Complexity: 822

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)OCC2C3C(C(O2)N4C=NC5=C(N=C(N=C54)Cl)N)OC(O3)(C)C

Technology Process of [4-(6-Amino-2-chloropurin-9-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methyl 4-methylbenzenesulfonate

There total 3 articles about [4-(6-Amino-2-chloropurin-9-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methyl 4-methylbenzenesulfonate 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: 85.0%

((3aR,4R,6R,6aR)-6-(6-amino-2-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol (24639-06-3) + p-toluenesulfonyl chloride (98-59-9) → 2-chloro-O2',O3'-isopropylidene-O5'-(toluene-4-sulfonyl)-adenosine (53458-44-9)

Guidance literature:

With pyridine; at -10 ℃;

DOI:10.1016/j.bmcl.2011.05.128 DOI:10.1016/j.bmcl.2011.11.071

Reference yield:

2-Chloroadenosine (146-77-0) → 2-chloro-O2',O3'-isopropylidene-O5'-(toluene-4-sulfonyl)-adenosine (53458-44-9)

Guidance literature:

Multi-step reaction with 2 steps

1: toluene-4-sulfonic acid / water / 1 h / 20 °C

2: dmap / dichloromethane / 20 °C

With dmap; toluene-4-sulfonic acid; In dichloromethane; water;

DOI:10.1111/cbdd.13119

Reference yield:

→ 2-chloro-O2',O3'-isopropylidene-O5'-(toluene-4-sulfonyl)-adenosine (53458-44-9)

Guidance literature:

Adenosin 2a, Tosylchlorid;

DOI:10.1021/jm00257a014

upstream raw materials:

((3aR,4R,6R,6aR)-6-(6-amino-2-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol

p-toluenesulfonyl chloride

2-Chloroadenosine

Downstream raw materials:

C₂₀H₂₇F₂N₅O₄

C₁₉H₂₅F₂N₅O₄

C₂₀H₂₆F₃N₅O₄

C₁₇H₂₅N₅O₄