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

Base Information

• Chemical Name: O6-Benzyl-N2,3-etheno-2'-phenoxythioxoMethyl-3',5'-O-[tetrakis(isopropyl)-1,3-disiloxanediyl] Guanosine
• CAS No.: 148437-93-8
• Molecular Formula: C38H49N5O7SSi2
• Molecular Weight: 778
• Mol file: 148437-93-8.mol

Synonyms:O6-Benzyl-N2,3-etheno-2'-phenoxythioxoMethyl-3',5'-O-[tetrakis(isopropyl)-1,3-disiloxanediyl] Guanosine;1-[2-O-(PhenoxythioxoMethyl)-3,5-O-[1,1,3,3-tetrakis(1-Methylethyl)-1,3-disiloxanediyl]-β-D-ribofuranosyl]-4-(phenylMethoxy)-1H-iMidazo[2,1-b]purine

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

Chemical Property:

• PSA: 144.71000
• LogP: 8.26090
• Solubility.: Chloroform, DMSO, Methanol

Purity/Quality:

97% ^*data from raw suppliers

O6-Benzyl-N2,3-etheno-2’-phenoxythioxomethyl-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:

• Uses: Protected Guanosine derivative.

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

There total 7 articles about O6-Benzyl-N2,3-etheno-2'-phenoxythioxoMethyl-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: 50.0%

O6-Benzyl-N2,3-etheno-3',5'-O-(1,1,3,3-tetraisopropyldisiloxa-1,3-diyl)guanosine (148437-91-6) + phenylcarbonochloridothioate (1005-56-7) → O6-Benzyl-N2,3-etheno-2'-O--3',5'-O-(1,1,3,3-tetraisopropyldisiloxa-1,3-diyl)guanosine (148437-93-8)

Guidance literature:

With dmap; In acetonitrile; at 24 ℃; for 12h;

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'-O--3',5'-O-(1,1,3,3-tetraisopropyldisiloxa-1,3-diyl)guanosine (148437-93-8)

Guidance literature:

Multi-step reaction with 5 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

With pyridine; dmap; sodium hydroxide; sodium acetate; acetic acid; triphenylphosphine; potassium iodide; diethylazodicarboxylate; In 1,4-dioxane; methanol; ethanol; water; acetonitrile;

DOI:10.1021/jo00061a033

Reference yield:

2-amino-6-benzyloxy-9-β-D-ribofuranosylpurine (4552-61-8) → O6-Benzyl-N2,3-etheno-2'-O--3',5'-O-(1,1,3,3-tetraisopropyldisiloxa-1,3-diyl)guanosine (148437-93-8)

Guidance literature:

Multi-step reaction with 3 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

With pyridine; dmap; sodium acetate; acetic acid; potassium iodide; In ethanol; water; acetonitrile;

DOI:10.1021/jo00061a033

upstream raw materials:

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

phenylcarbonochloridothioate

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

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

Downstream raw materials:

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

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

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