7-Iodo-2',3'-Dideoxy-7-Deaza-Guanosine

Base Information

• Chemical Name: 7-Iodo-2',3'-Dideoxy-7-Deaza-Guanosine
• CAS No.: 114748-67-3
• Molecular Formula: C11H13IN4O3
• Molecular Weight: 376.15
• Mol file: 114748-67-3.mol

Synonyms:7-Iodo-2',3'-Dideoxy-7-Deaza-Guanosine;7-I-7-Deaza-ddG;2-Amino-3,7-dihydro-5-iodo-7-[(2R,5S)-tetrahydro-5-(hydroxymethyl)-2-furanyl]-4H-pyrrolo[2,3-d]pyrimidin-4-one

Chemical Property of 7-Iodo-2',3'-Dideoxy-7-Deaza-Guanosine

Chemical Property:

• PKA: 10.28±0.20(Predicted)
• PSA: 106.16000
• Density: 2.35±0.1 g/cm3(Predicted)
• LogP: 1.16250

Purity/Quality:

98%, ^*data from raw suppliers

7-Deaza-2',3'-dideoxy-7-iodoguanosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 7-Iodo-2',3'-Dideoxy-7-Deaza-Guanosine

There total 10 articles about 7-Iodo-2',3'-Dideoxy-7-Deaza-Guanosine 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: 81.0%

2-Amino-5-iodo-7-((2R,5S)-5-trityloxymethyl-tetrahydro-furan-2-yl)-3,7-dihydro-pyrrolo[2,3-d]pyrimidin-4-one (114748-66-2) → 7-iodo-2',3'-dideoxy-7-deazaguanosine (114748-67-3)

Guidance literature:

With formic acid; for 0.166667h; Ambient temperature;

DOI:10.1016/S0040-4039(00)80417-7

Reference yield:

7-(2'-Desoxy-β-D-erythro-pentofuranosyl)-4-methoxy-2-methylthio-7H-pyrrolo<2,3-d>pyrimidin (98891-39-5) → 7-iodo-2',3'-dideoxy-7-deazaguanosine (114748-67-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 94 percent / DMAP, Et₃N / pyridine / 16.5 h / 65 °C

2: 1.) phenyl chlorothiocarbonate, DMAP; 2.) n-Bu₃SnH, AIBN / 1.) CH₂Cl₂, RT, 3 h; 2.) toluene, 105 deg C, 10 min

3: 96 percent / N-iodosuccinimide / dimethylformamide / 16 h / Ambient temperature

4: 97 percent / sodium thiocresolate / hexamethylphosphoric acid triamide; toluene / 4.5 h / Heating

5: 1.) MCBA; 2.) NH₃ / 1.) CH₂Cl₂, from 0 deg C to RT, 1 h; 2.) dioxane, 100 deg C, 2 h

6: 81 percent / formic acid / 0.17 h / Ambient temperature

With dmap; N-iodo-succinimide; formic acid; sodium 4-mercaptobenzoate; 2,2'-azobis(isobutyronitrile); ammonia; tri-n-butyl-tin hydride; triethylamine; phenylcarbonochloridothioate; 3-chlorobenzoate; In pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4039(00)80417-7

Reference yield:

4-Methoxy-2-methylsulfanyl-7-((2R,5S)-5-trityloxymethyl-tetrahydro-furan-2-yl)-7H-pyrrolo[2,3-d]pyrimidine (114748-63-9) → 7-iodo-2',3'-dideoxy-7-deazaguanosine (114748-67-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 96 percent / N-iodosuccinimide / dimethylformamide / 16 h / Ambient temperature

2: 97 percent / sodium thiocresolate / hexamethylphosphoric acid triamide; toluene / 4.5 h / Heating

3: 1.) MCBA; 2.) NH₃ / 1.) CH₂Cl₂, from 0 deg C to RT, 1 h; 2.) dioxane, 100 deg C, 2 h

4: 81 percent / formic acid / 0.17 h / Ambient temperature

With N-iodo-succinimide; formic acid; sodium 4-mercaptobenzoate; ammonia; 3-chlorobenzoate; In N,N,N,N,N,N-hexamethylphosphoric triamide; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4039(00)80417-7

upstream raw materials:

2-Amino-5-iodo-7-((2R,5S)-5-trityloxymethyl-tetrahydro-furan-2-yl)-3,7-dihydro-pyrrolo[2,3-d]pyrimidin-4-one

7-(2'-Desoxy-β-D-erythro-pentofuranosyl)-4-methoxy-2-methylthio-7H-pyrrolo<2,3-d>pyrimidin

4-Methoxy-2-methylsulfanyl-7-((2R,5S)-5-trityloxymethyl-tetrahydro-furan-2-yl)-7H-pyrrolo[2,3-d]pyrimidine

(2R,3S,5R)-5-(4-Methoxy-2-methylsulfanyl-pyrrolo[2,3-d]pyrimidin-7-yl)-2-trityloxymethyl-tetrahydro-furan-3-ol

Downstream raw materials:

N-{3-[2-Amino-7-((2R,5S)-5-hydroxymethyl-tetrahydro-furan-2-yl)-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-5-yl]-prop-2-ynyl}-2,2,2-trifluoro-acetamide

N-{3-[2-Amino-4-hydroxy-7-((2R,5S)-5-hydroxymethyl-tetrahydro-furan-2-yl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl]-prop-2-ynyl}-2,2,2-trifluoro-acetamide

N-{3-[2-Amino-7-((S)-5-hydroxymethyl-tetrahydro-furan-2-yl)-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-5-yl]-prop-2-ynyl}-2,2,2-trifluoro-acetamide