N2-(1,1,4,4-Tetramethyldisilylazacyclopentanyl)-O6-benzyl-8-bromo-N9-[3’,5’-O-(1,1,3,3-tetrakis(isopropyl)-1,3-disiloxanediyl)--D-2’-deoxyribofuranosyl]guanine

Base Information

• Chemical Name: N2-(1,1,4,4-Tetramethyldisilylazacyclopentanyl)-O6-benzyl-8-bromo-N9-[3’,5’-O-(1,1,3,3-tetrakis(isopropyl)-1,3-disiloxanediyl)--D-2’-deoxyribofuranosyl]guanine
• CAS No.: 328394-28-1
• Molecular Formula: C₃₅H₅₈BrN₅O₅Si₄
• Molecular Weight: 821.122
• Mol file: 328394-28-1.mol

Synonyms:N²-(1,1,4,4-tetramethyldisilylazacyclopentanyl)-O⁶-benzyl-8-bromo-N9-[3',5'-O-(1,1,3,3-tetrakis(isopropyl)-1,3-disiloxanediyl)-β-D-2'-deoxyribofuranosyl]guanine

Chemical Property of N2-(1,1,4,4-Tetramethyldisilylazacyclopentanyl)-O6-benzyl-8-bromo-N9-[3’,5’-O-(1,1,3,3-tetrakis(isopropyl)-1,3-disiloxanediyl)--D-2’-deoxyribofuranosyl]guanine

Chemical Property:

• Melting Point: 93-95°C
• Boiling Point: 713.3±70.0 °C(Predicted)
• PKA: 0.42±0.20(Predicted)
• Density: 1.26±0.1 g/cm3(Predicted)
• Solubility.: Chloroform, DMF, DMSO, Ethyl Acetate, Methanol

Purity/Quality:

98% ^*data from raw suppliers

N2-(1,1,4,4-Tetramethyldisilylazacyclopentanyl)-O6-benzyl-8-bromo-N9-[3’,5’-O-(1,1,3,3-tetrakis(isopropyl)-1,3-disiloxanediyl)-β-D-2’-deoxyribofuranosyl]guanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: N2-(1,1,4,4-Tetramethyldisilylazacyclopentanyl)-O6-benzyl-8-bromo-N9-[3’,5’-O-(1,1,3,3-tetrakis(isopropyl)-1,3-disiloxanediyl)-β-D-2’-deoxyribofuranosyl]guanine (cas# 328394-28-1) is a compound useful in organic synthesis.

Technology Process of N2-(1,1,4,4-Tetramethyldisilylazacyclopentanyl)-O6-benzyl-8-bromo-N9-[3’,5’-O-(1,1,3,3-tetrakis(isopropyl)-1,3-disiloxanediyl)--D-2’-deoxyribofuranosyl]guanine

There total 7 articles about N2-(1,1,4,4-Tetramethyldisilylazacyclopentanyl)-O6-benzyl-8-bromo-N9-[3’,5’-O-(1,1,3,3-tetrakis(isopropyl)-1,3-disiloxanediyl)--D-2’-deoxyribofuranosyl]guanine 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: 85.0%

1,2-bis-(chlorodimethylsilyl)ethane (13528-93-3) + O6-benzyl-8-bromo-N9-[3',5'-O-(1,1,3,3-tetrakis(isopropyl)-1,3-disiloxanediyl)-β-D-2'-deoxyribofuranosyl]guanine (328394-26-9) → N2-(1,1,4,4-tetramethyldisilylazacyclopentanyl)-O6-benzyl-8-bromo-N9-[3',5'-O-(1,1,3,3-tetrakis(isopropyl)-1,3-disiloxanediyl)-β-D-2'-deoxyribofuranosyl]guanine (328394-28-1)

Guidance literature:

O⁶-benzyl-8-bromo-N9-[3',5'-O-(1,1,3,3-tetrakis(isopropyl)-1,3-disiloxanediyl)-β-D-2'-deoxyribofuranosyl]guanine; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.25h;

1,2-bis-(chlorodimethylsilyl)ethane; In tetrahydrofuran; at 20 ℃; for 0.333333h;

DOI:10.1021/ja0487022

Reference yield:

1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane (69304-37-6) → N2-(1,1,4,4-tetramethyldisilylazacyclopentanyl)-O6-benzyl-8-bromo-N9-[3',5'-O-(1,1,3,3-tetrakis(isopropyl)-1,3-disiloxanediyl)-β-D-2'-deoxyribofuranosyl]guanine (328394-28-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 91 percent / pyridine / 0 - 20 °C

2.1: 76 percent / PPh₃; DEAD / dioxane / 0 - 20 °C

3.1: LiHMDS / tetrahydrofuran / 0.25 h / -78 °C

3.2: 85 percent / tetrahydrofuran / 0.33 h / 20 °C

With pyridine; triphenylphosphine; lithium hexamethyldisilazane; diethylazodicarboxylate; In tetrahydrofuran; 1,4-dioxane;

DOI:10.1021/ja0487022

Reference yield:

8-bromo-2'-deoxyguanosine (13389-03-2) → N2-(1,1,4,4-tetramethyldisilylazacyclopentanyl)-O6-benzyl-8-bromo-N9-[3',5'-O-(1,1,3,3-tetrakis(isopropyl)-1,3-disiloxanediyl)-β-D-2'-deoxyribofuranosyl]guanine (328394-28-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 91 percent / pyridine / 0 - 20 °C

2.1: 76 percent / PPh₃; DEAD / dioxane / 0 - 20 °C

3.1: LiHMDS / tetrahydrofuran / 0.25 h / -78 °C

3.2: 85 percent / tetrahydrofuran / 0.33 h / 20 °C

With pyridine; triphenylphosphine; lithium hexamethyldisilazane; diethylazodicarboxylate; In tetrahydrofuran; 1,4-dioxane;

DOI:10.1021/ja0487022

upstream raw materials:

1,2-bis-(chlorodimethylsilyl)ethane

O⁶-benzyl-8-bromo-N9-[3',5'-O-(1,1,3,3-tetrakis(isopropyl)-1,3-disiloxanediyl)-β-D-2'-deoxyribofuranosyl]guanine

1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane

8-bromo-2'-deoxyguanosine

Downstream raw materials:

N²-(2'-deoxyguanosin-8-yl)-2-amino-3-methylimidazo[4,5-f]quinoline

Refernces

• 1、 Wang,Rizzo. "Synthesis of the C8-deoxyguanosine adduct of the food mutagen IQ.". . p. 565 - 568. Retrieved 2007/10/03.