7-Deaza-2'-deoxyxanthosine

Base Information

• Chemical Name: 7-Deaza-2'-deoxyxanthosine
• CAS No.: 96022-82-1
• Molecular Formula: C₁₁H₁₃N₃O₅
• Molecular Weight: 267.241
• DSSTox Substance ID: DTXSID00473816
• Nikkaji Number: J729.856K
• Wikidata: Q82303451
• Mol file: 96022-82-1.mol

Synonyms:7-deaza-2'-deoxyxanthosine;dzaX

Chemical Property of 7-Deaza-2'-deoxyxanthosine

Chemical Property:

• PSA: 120.34000
• LogP: -1.34140
• XLogP3: -1.1
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 267.08552052
• Heavy Atom Count: 19
• Complexity: 404

Purity/Quality:

97% ^*data from raw suppliers

7-Deaza-2''-deoxyxanthosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(OC1N2C=CC3=C2NC(=O)NC3=O)CO)O
• Isomeric SMILES: C1[C@@H]([C@H](O[C@H]1N2C=CC3=C2NC(=O)NC3=O)CO)O

Technology Process of 7-Deaza-2'-deoxyxanthosine

There total 5 articles about 7-Deaza-2'-deoxyxanthosine 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: 60.0%

7-(2'-Desoxy-β-D-erythro-pentafuranosyl)-2,4-dimethoxy-7H-pyrrolo<2,3-d>pyrimidin (96022-79-6) → 7-(2-Desoxy-β-D-erythro-pentofuranosyl)-7H-pyrrolo<2,3-d>pyrimidin-2,4(1H,3H)-dion (96022-82-1)

Guidance literature:

With hydrogen bromide; acetic acid; In tetrahydrofuran; Heating;

Reference yield:

4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-amine (84955-31-7) → 7-(2-Desoxy-β-D-erythro-pentofuranosyl)-7H-pyrrolo<2,3-d>pyrimidin-2,4(1H,3H)-dion (96022-82-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) 25percent HCl, NaNO₂; 2.) CuCl / 1.) H₂O, 5 deg C, 15 min 2.) 80 deg C, 15 min

2: 94 percent / methanol / 168 h / Heating

3: 67 percent / benzyltriethylammoniumchloride, 50percent NaOH / CH₂Cl₂ / 0.17 h

4: 60 percent / HBr/glacial acetic acid / tetrahydrofuran / Heating

With hydrogenchloride; sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; hydrogen bromide; acetic acid; copper(l) chloride; sodium nitrite; In tetrahydrofuran; methanol; dichloromethane;

Reference yield:

2,4-dimethoxy-7H-pyrrolo<2,3-d>pyrimidine (90057-09-3) → 7-(2-Desoxy-β-D-erythro-pentofuranosyl)-7H-pyrrolo<2,3-d>pyrimidin-2,4(1H,3H)-dion (96022-82-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 67 percent / benzyltriethylammoniumchloride, 50percent NaOH / CH₂Cl₂ / 0.17 h

2: 60 percent / HBr/glacial acetic acid / tetrahydrofuran / Heating

With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; hydrogen bromide; acetic acid; In tetrahydrofuran; dichloromethane;

upstream raw materials:

7-(2'-Desoxy-β-D-erythro-pentafuranosyl)-2,4-dimethoxy-7H-pyrrolo<2,3-d>pyrimidin

4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-amine

2,4-dimethoxy-7H-pyrrolo<2,3-d>pyrimidine

2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidine

Refernces

• 1、 Seela, Frank,Driller, Hansjuergen,Liman, Ulrich. "7-Deaza Isosters of 2'-Deoxyxanthosine and 2'-Deoxyspongosine - Synthesis via Glycosylation of 2,4-Dichloro-7H-pyrrolopyrimidine". . p. 312 - 320. Retrieved 2007/10/02.