2',3'-O-ISOPROPYLIDENE-5'-O-TOLUOLSULFONYL-ADENOSINE

Base Information

• Chemical Name: 2',3'-O-ISOPROPYLIDENE-5'-O-TOLUOLSULFONYL-ADENOSINE
• CAS No.: 5605-63-0
• Molecular Formula: C20H23N5O6S
• Molecular Weight: 461.499
• Mol file: 5605-63-0.mol

Synonyms:2',3'-O-ISOPROPYLIDENE-5'-O-TOLUOLSULFONYL-ADENOSINE

Chemical Property of 2',3'-O-ISOPROPYLIDENE-5'-O-TOLUOLSULFONYL-ADENOSINE

Chemical Property:

• PSA: 149.06000
• LogP: 3.03460
• Solubility.: Chloroform

Purity/Quality:

97% ^*data from raw suppliers

2'',3''-O-Isopropylidene-5''-O-tosyladenosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 2'',3''-O-Isopropylidene-5''-O-tosyladenosine is an intermediate in the synthesis of Adenosine 5’-Diphosphate-13C5 Ammonium Salt Hydrate (A281697), which is the isotope labelled analog of Adenosine 5’-Diphosphate Ammonium Salt Hydrate (A281700); a nucleoside diphosphate that interacts with a family of ADP receptors found on platelets (P2Y1, P2Y12 and P2X1), to induce platelet activation. ADP in the blood is converted to adenosine by the action of ecto-ADPases, inhibiting further platelet activation via adenosine receptors.

Technology Process of 2',3'-O-ISOPROPYLIDENE-5'-O-TOLUOLSULFONYL-ADENOSINE

There total 3 articles about 2',3'-O-ISOPROPYLIDENE-5'-O-TOLUOLSULFONYL-ADENOSINE 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: 88.0%

2',3'-isopropylidene adenosine (362-75-4) + p-toluenesulfonyl chloride (98-59-9) → ((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl 4-methylbenzenesulfonate (5605-63-0)

Guidance literature:

In pyridine; at -20 ℃; for 72h;

DOI:10.1021/jo9907742

Reference yield:

adenosine (58-61-7) → ((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl 4-methylbenzenesulfonate (5605-63-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 83 percent / Di-p-nitrophenyl hydrogen phosphate / acetone

2: 57 percent / pyridine

With pyridine; Bis(p-nitrophenyl) phosphate; In acetone;

Reference yield:

→ ((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl 4-methylbenzenesulfonate (5605-63-0)

Guidance literature:

2':3'-O-Isopropyliden-adenin + p-Toluolsulfochlorid + Pyridin.;

upstream raw materials:

2',3'-isopropylidene adenosine

p-toluenesulfonyl chloride

adenosine

Downstream raw materials:

(S)-5’-(S)-(3-amino-3-carboxypropyl)-5’-thioadenosine

5'-acetylthio-5'-deoxy-2',3'-O-isopropylidene adenosine

9-{(3aR,4R,6R,6aR)-2,2-Dimethyl-6-[4-((1Z,4Z,9Z,15Z)-10,15,20-tri-p-tolyl-porphyrin-5-yl)-phenoxymethyl]-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl}-9H-purin-6-ylamine

5'-deoxy-5'-methylamino-2',3'-O,O-(1-methylethylidene)adenosine