[(1S,2R,3R)-3-(2-amino-6-iodopurin-9-yl)-2-(benzoyloxymethyl)cyclobutyl]methyl benzoate

Base Information

• Chemical Name: [(1S,2R,3R)-3-(2-amino-6-iodopurin-9-yl)-2-(benzoyloxymethyl)cyclobutyl]methyl benzoate
• CAS No.: 156126-83-9
• Molecular Formula: C25H22IN5O4
• Molecular Weight: 583.385
• DSSTox Substance ID: DTXSID90935372
• Wikidata: Q82911410
• Mol file: 156126-83-9.mol

Synonyms:156126-83-9;DTXSID90935372;[3-(2-Imino-6-iodo-1,2-dihydro-9H-purin-9-yl)cyclobutane-1,2-diyl]bis(methylene) dibenzoate

Chemical Property of [(1S,2R,3R)-3-(2-amino-6-iodopurin-9-yl)-2-(benzoyloxymethyl)cyclobutyl]methyl benzoate

Chemical Property:

• XLogP3: 4.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 9
• Exact Mass: 583.07165
• Heavy Atom Count: 35
• Complexity: 747

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(C1N2C=NC3=C2N=C(N=C3I)N)COC(=O)C4=CC=CC=C4)COC(=O)C5=CC=CC=C5
• Isomeric SMILES: C1[C@@H]([C@H]([C@@H]1N2C=NC3=C2N=C(N=C3I)N)COC(=O)C4=CC=CC=C4)COC(=O)C5=CC=CC=C5

Technology Process of [(1S,2R,3R)-3-(2-amino-6-iodopurin-9-yl)-2-(benzoyloxymethyl)cyclobutyl]methyl benzoate

There total 7 articles about [(1S,2R,3R)-3-(2-amino-6-iodopurin-9-yl)-2-(benzoyloxymethyl)cyclobutyl]methyl benzoate 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: 76.0%

2-amino-6-iodopurine tetra-n-butylammonium salt + C21H19F3O7S (163928-93-6) → <1S-(1α,2β,3α)>-3-(2-Amino-6-iodo-7H-purin-7-yl)-1,2-cyclobutanedimethanol dibenzoate ester (163928-96-9) + <1S-(1α,2β,3α)>-3-(2-Amino-6-iodo-9H-purin-9-yl)-1,2-cyclobutanedimethanol dibenzoate ester (156126-83-9)

Guidance literature:

In dichloromethane; at 25 ℃; regioselective reaction;

DOI:10.1021/op970214+

Reference yield: 76.0%

C22H19F3O6 + 2-amino-6-iodopurine tetra-n-butylammonium salt → <1S-(1α,2β,3α)>-3-(2-Amino-6-iodo-7H-purin-7-yl)-1,2-cyclobutanedimethanol dibenzoate ester (163928-96-9) + <1S-(1α,2β,3α)>-3-(2-Amino-6-iodo-9H-purin-9-yl)-1,2-cyclobutanedimethanol dibenzoate ester (156126-83-9)

Guidance literature:

In dichloromethane; Yield given; 1.) ice bath temp., 30 min, 2.) room temp., overnight;

DOI:10.1021/jo00114a047

Reference yield: 70.0%

6-Iodo-9H-purin-2-amine ion(1-) triethyl(phenylmethyl)ammonium salt + C21H19F3O7S (163928-93-6) → <1S-(1α,2β,3α)>-3-(2-Amino-6-iodo-7H-purin-7-yl)-1,2-cyclobutanedimethanol dibenzoate ester (163928-96-9) + <1S-(1α,2β,3α)>-3-(2-Amino-6-iodo-9H-purin-9-yl)-1,2-cyclobutanedimethanol dibenzoate ester (156126-83-9)

Guidance literature:

In dichloromethane; at 25 ℃; regioselective reaction;

DOI:10.1021/op970214+

upstream raw materials:

C₂₁H₁₉F₃O₇S

Downstream raw materials:

9-((1R,2R,3S)-2,3-bis(hydroxymethyl)cyclobutyl)-2-amino-1H-purin-6(9H)-one