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: O6-Benzyl-8-bromo-N9-[3’,5’-O-(1,1,3,3-tetrakis(isopropyl)-1,3-disiloxanediyl)--D-2’-deoxyribofuranosyl]guanine
• CAS No.: 328394-26-9
• Molecular Formula: C29H44BrN5O5Si2
• Molecular Weight: 678.774
• Mol file: 328394-26-9.mol

Synonyms:8-Bromo-2'-deoxy-6-O-(phenylmethyl)-3',5'-O-[1,1,3,3-tetrakis(1-methylethyl)-1,3-disiloxanediyl]guanosine;O6-Benzyl-8-bromo-N9-[3',5'-O-(1,1,3,3-tetrakis(isopropyl)-1,3-disiloxanediyl)-|A-D-2'-deoxyribofuranosyl]guanine;

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

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 125-127°C
• Boiling Point: 690.252°C at 760 mmHg
• Flash Point: 371.251°C
• PSA: 116.50000
• Density: 1.374g/cm³
• LogP: 6.92400
• Solubility.: Acetone, Chloroform, DMF, DMSO, Ethyl Acetate, Methanol

Purity/Quality:

97% ^*data from raw suppliers

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:

SDS file from LookChem

Useful:

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

There total 6 articles about 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: 76.0%

benzyl alcohol (100-51-6,185532-71-2) + 8-bromo-N9-[3',5'-O-(1,1,3,3-tetrakis(isopropyl)-1,3-disiloxanediyl)-β-D-2'-deoxyribofuranosyl]guanine (769141-88-0) → 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)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In 1,4-dioxane; at 0 - 20 ℃;

DOI:10.1021/ja0487022

Reference yield: 38.0%

2-Amino-1-methylbenzimidazole (1622-57-7) + N'-[6-benzyloxy-8-bromo-9-(5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl)-9H-purin-2-yl]-N,N-dimethyl-formamidine → N,N-dimethyl-N'-(1-methyl-1H-benzoimidazol-2-yl)-formamidine + 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)

Guidance literature:

With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In toluene; at 100 ℃; for 12h;

DOI:10.1021/ol006968h

Reference yield:

1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane (69304-37-6) → 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)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / pyridine / 0 - 20 °C

2: 76 percent / PPh₃; DEAD / dioxane / 0 - 20 °C

With pyridine; triphenylphosphine; diethylazodicarboxylate; In 1,4-dioxane;

DOI:10.1021/ja0487022

upstream raw materials:

2-Amino-1-methylbenzimidazole

benzyl alcohol

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

Downstream raw materials:

C₃₉H₆₀BrN₅O₉Si₂

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

O⁶-benzyl-8-[(1,1'-biphenyl)-4-ylamino]-N9-[3',5'-O-(1,1,3,3-tetrakis(isopropyl)-1,3-disiloxanediyl)-β-D-2'-deoxyribofuranosyl]guanine

N-(2'-deoxypyranosin-8-yl)-4-methylaniline

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