O6-Benzyl-N2,3-etheno-2'-deoxy-3',5'-O-[tetrakis(isopropyl)-1,3-disiloxanediyl] Guanosine

Base Information

• Chemical Name: O6-Benzyl-N2,3-etheno-2'-deoxy-3',5'-O-[tetrakis(isopropyl)-1,3-disiloxanediyl] Guanosine
• CAS No.: 148437-94-9
• Molecular Formula: C31H45N5O5Si2
• Molecular Weight: 623.8905
• Mol file: 148437-94-9.mol

Synonyms:O6-Benzyl-N2,3-etheno-2'-deoxy-3',5'-O-[tetrakis(isopropyl)-1,3-disiloxanediyl] Guanosine

Chemical Property of O6-Benzyl-N2,3-etheno-2'-deoxy-3',5'-O-[tetrakis(isopropyl)-1,3-disiloxanediyl] Guanosine

Chemical Property:

• PSA: 94.16000
• LogP: 6.90190
• Solubility.: Chloroform, DMSO, Methanol
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 8
• Exact Mass: 623.29592262
• Heavy Atom Count: 43
• Complexity: 924

Purity/Quality:

97% ^*data from raw suppliers

O6-Benzyl-N2,3-etheno-2’-deoxy-3’,5’-O-[tetrakis(isopropyl)-1,3-disiloxanediyl]Guanosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)[Si]1(OCC2C(CC(O2)N3C=NC4=C3N5C=CN=C5N=C4OCC6=CC=CC=C6)O[Si](O1)(C(C)C)C(C)C)C(C)C
• Isomeric SMILES: CC(C)[Si]1(OC[C@@H]2[C@H](C[C@@H](O2)N3C=NC4=C3N5C=CN=C5N=C4OCC6=CC=CC=C6)O[Si](O1)(C(C)C)C(C)C)C(C)C
• Uses: Protected Guanosine derivative.

Technology Process of O6-Benzyl-N2,3-etheno-2'-deoxy-3',5'-O-[tetrakis(isopropyl)-1,3-disiloxanediyl] Guanosine

There total 8 articles about O6-Benzyl-N2,3-etheno-2'-deoxy-3',5'-O-[tetrakis(isopropyl)-1,3-disiloxanediyl] 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: 65.0%

O6-Benzyl-N2,3-etheno-2'-O--3',5'-O-(1,1,3,3-tetraisopropyldisiloxa-1,3-diyl)guanosine (148437-93-8) → O6-Benzyl-N2,3-etheno-2'-deoxy-3',5'-O-(1,1,3,3-tetraisopropyldisiloxa-1,3-diyl)guanosine (148437-94-9)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; for 3h; Heating;

DOI:10.1021/jo00061a033

Reference yield:

N2-(2-methylpropanoyl)-2',3',5'-tris-O-(2-methylpropanoyl)guanosine (70337-80-3) → O6-Benzyl-N2,3-etheno-2'-deoxy-3',5'-O-(1,1,3,3-tetraisopropyldisiloxa-1,3-diyl)guanosine (148437-94-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 48.3 percent / triphenylphosphine, diethyl azodicarboxylate / dioxane / 48 h / 24 °C

2: 93 percent / NaOH / methanol / 48 h / Ambient temperature

3: 47.9 percent / aq. sodium acetate, aq. acetic acid, KI / ethanol; H₂O / 30 h / 37 - 40 °C / pH=4.5

4: 89 percent / pyridine / 12 h

5: 50 percent / 4-(dimethylamino)pyridine / acetonitrile / 12 h / 24 °C

6: 65 percent / tributyltin hydride, azobisisobutyronitrile / toluene / 3 h / Heating

With pyridine; dmap; sodium hydroxide; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium acetate; acetic acid; triphenylphosphine; potassium iodide; diethylazodicarboxylate; In 1,4-dioxane; methanol; ethanol; water; toluene; acetonitrile;

DOI:10.1021/jo00061a033

Reference yield:

2-amino-6-benzyloxy-9-β-D-ribofuranosylpurine (4552-61-8) → O6-Benzyl-N2,3-etheno-2'-deoxy-3',5'-O-(1,1,3,3-tetraisopropyldisiloxa-1,3-diyl)guanosine (148437-94-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 47.9 percent / aq. sodium acetate, aq. acetic acid, KI / ethanol; H₂O / 30 h / 37 - 40 °C / pH=4.5

2: 89 percent / pyridine / 12 h

3: 50 percent / 4-(dimethylamino)pyridine / acetonitrile / 12 h / 24 °C

4: 65 percent / tributyltin hydride, azobisisobutyronitrile / toluene / 3 h / Heating

With pyridine; dmap; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium acetate; acetic acid; potassium iodide; In ethanol; water; toluene; acetonitrile;

DOI:10.1021/jo00061a033

upstream raw materials:

O⁶-Benzyl-N²,3-etheno-2'-O--3',5'-O-(1,1,3,3-tetraisopropyldisiloxa-1,3-diyl)guanosine

N²-(2-methylpropanoyl)-2',3',5'-tris-O-(2-methylpropanoyl)guanosine

2-amino-6-benzyloxy-9-β-D-ribofuranosylpurine

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

Downstream raw materials:

O⁶-Benzyl-N²,3-etheno-2'-deoxyguanosine

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