5-(6-Aminopurin-9-yl)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]oxolan-3-ol

Base Information

• Chemical Name: 5-(6-Aminopurin-9-yl)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]oxolan-3-ol
• CAS No.: 17331-22-5
• Molecular Formula: C31H31 N5 O5
• Molecular Weight: 553.618
• DSSTox Substance ID: DTXSID70398087
• Mol file: 17331-22-5.mol

Synonyms:5-(6-aminopurin-9-yl)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]oxolan-3-ol;DMT-dA;ST055622;DTXSID70398087;AKOS024282332;J-010895

Chemical Property of 5-(6-Aminopurin-9-yl)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]oxolan-3-ol

Chemical Property:

• Melting Point: 97-98 °C(Solv: chloroform (67-66-3); ligroine (8032-32-4))
• Boiling Point: 785.1±70.0 °C(Predicted)
• PKA: 13.75±0.60(Predicted)
• PSA: 126.77000
• Density: 1.35±0.1 g/cm3(Predicted)
• LogP: 4.66400
• Storage Temp.: −20°C
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 9
• Exact Mass: 553.23251911
• Heavy Atom Count: 41
• Complexity: 793

Purity/Quality:

97% ^*data from raw suppliers

5''-O-(4,4''-Dimethoxytrityl)-2''-deoxyadenosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)C(C2=CC=CC=C2)(C3=CC=C(C=C3)OC)OCC4C(CC(O4)N5C=NC6=C(N=CN=C65)N)O
• Uses: 5''-O-(4,4''-dimethoxytrityl)-2''-deoxyadenosine (CAS# 17331-22-5) is a nucleoside used to synthesize oligonucleotides for triazole- and tetrazole-?bridged nucleic acids.

Technology Process of 5-(6-Aminopurin-9-yl)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]oxolan-3-ol

There total 13 articles about 5-(6-Aminopurin-9-yl)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]oxolan-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: 95.0%

N6-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyadenosine (64325-78-6) → 5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-deoxyadenosine (17331-22-5)

Guidance literature:

N₆-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyadenosine; With pyridine; 1-methyl-1H-imidazole; acetic anhydride; for 144h;

With ammonium hydroxide; at 55 ℃; for 16.5h;

DOI:10.1016/j.bmcl.2016.06.042

Reference yield: 90.0%

2-azidomethyl-N-(9-{5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-9H-purin-6-yl)-benzamide (329781-61-5) → 5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-deoxyadenosine (17331-22-5)

Guidance literature:

With diphenyl(methyl)phosphine; In 1,4-dioxane; water; at 20 ℃; for 0.333333h;

DOI:10.1016/S0040-4039(00)02183-3

Reference yield: 86.0%

4,4'-dimethoxytrityl chloride (40615-36-9) + 2'-deoxy-D-adenosine (958-09-8,7005-15-4) → 5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-deoxyadenosine (17331-22-5)

Guidance literature:

With 1H-imidazole; methanesulfonic acid; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃; for 2h;

DOI:10.1021/jo990051i

upstream raw materials:

4,4'-dimethoxytrityl chloride

2'-deoxy-D-adenosine

(9-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-9H-purin-6-yl)-carbamic acid 2-(5-dimethylamino-naphthalene-1-sulfonyl)-ethyl ester

2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-N⁶-phthaloyladenosine

Downstream raw materials:

Phosphoric acid diallyl ester (2R,3S,5R)-5-(6-amino-purin-9-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-furan-3-yl ester

Diisopropyl-phosphoramidous acid (2R,3S,5R)-5-(6-amino-purin-9-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-furan-3-yl ester methyl ester

5'-O-(4,4'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)-2'-deoxyadenosine

2'-deoxy-D-adenosine