β-D-1-(3-methyl-pyrimido[4,5-d]pyrimido[1,6-a]indol-10-yl)-5-O-(4,4'-dimethoxytrityl)-2-deoxyribose

Base Information

• Chemical Name: β-D-1-(3-methyl-pyrimido[4,5-d]pyrimido[1,6-a]indol-10-yl)-5-O-(4,4'-dimethoxytrityl)-2-deoxyribose
• CAS No.: 1356140-71-0
• Molecular Formula: C₄₀H₃₆N₄O₇
• Molecular Weight: 684.748
• Mol file: 1356140-71-0.mol

Synonyms:β-D-1-(3-methyl-pyrimido[4,5-d]pyrimido[1,6-a]indol-10-yl)-5-O-(4,4'-dimethoxytrityl)-2-deoxyribose

Chemical Property of β-D-1-(3-methyl-pyrimido[4,5-d]pyrimido[1,6-a]indol-10-yl)-5-O-(4,4'-dimethoxytrityl)-2-deoxyribose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of β-D-1-(3-methyl-pyrimido[4,5-d]pyrimido[1,6-a]indol-10-yl)-5-O-(4,4'-dimethoxytrityl)-2-deoxyribose

There total 3 articles about β-D-1-(3-methyl-pyrimido[4,5-d]pyrimido[1,6-a]indol-10-yl)-5-O-(4,4'-dimethoxytrityl)-2-deoxyribose 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: 89.0%

10-(β-D-2-deoxyribos-1-yl)-3-methyl-pyrimido[4,5-d]pyrimido[1,6-a]indol (1356140-70-9) + 4,4'-dimethoxytrityl chloride (40615-36-9) → β-D-1-(3-methyl-pyrimido[4,5-d]pyrimido[1,6-a]indol-10-yl)-5-O-(4,4'-dimethoxytrityl)-2-deoxyribose (1356140-71-0)

Guidance literature:

With pyridine; at 20 ℃; for 6h;

DOI:10.1039/c1ob06411h

Reference yield:

5-methyl-1H-indole (614-96-0) → β-D-1-(3-methyl-pyrimido[4,5-d]pyrimido[1,6-a]indol-10-yl)-5-O-(4,4'-dimethoxytrityl)-2-deoxyribose (1356140-71-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: dmap / acetonitrile / 20 °C

2.1: Triisopropyl borate; lithium diisopropyl amide / tetrahydrofuran / 3 h / 0 °C

2.2: pH 6 / aq. phosphate buffer

3.1: palladium diacetate; sodium carbonate; trisodium triphenylphosphine‐3,3′,3″‐trisulfonate / water; acetonitrile / 15 h / 45 °C / Inert atmosphere

4.1: pyridine / 6 h / 20 °C

With pyridine; dmap; Triisopropyl borate; palladium diacetate; sodium carbonate; trisodium triphenylphosphine‐3,3′,3″‐trisulfonate; lithium diisopropyl amide; In tetrahydrofuran; water; acetonitrile;

DOI:10.1039/c1ob06411h

Reference yield:

{1-[(tert-butoxy)carbonyl]-5-methyl-1H-indol-2-yl}boronic acid (475102-14-8) → β-D-1-(3-methyl-pyrimido[4,5-d]pyrimido[1,6-a]indol-10-yl)-5-O-(4,4'-dimethoxytrityl)-2-deoxyribose (1356140-71-0)

Guidance literature:

Multi-step reaction with 2 steps

1: palladium diacetate; sodium carbonate; trisodium triphenylphosphine‐3,3′,3″‐trisulfonate / water; acetonitrile / 15 h / 45 °C / Inert atmosphere

2: pyridine / 6 h / 20 °C

With pyridine; palladium diacetate; sodium carbonate; trisodium triphenylphosphine‐3,3′,3″‐trisulfonate; In water; acetonitrile;

DOI:10.1039/c1ob06411h

upstream raw materials:

10-(β-D-2-deoxyribos-1-yl)-3-methyl-pyrimido[4,5-d]pyrimido[1,6-a]indol

4,4'-dimethoxytrityl chloride

5-methyl-1H-indole

{1-[(tert-butoxy)carbonyl]-5-methyl-1H-indol-2-yl}boronic acid

Downstream raw materials:

β-D-1-(3-methyl-pyrimido[4,5-d]pyrimido[1,6-a]indol-10-yl)-5-O-(4,4'-dimethoxytrityl)-2-deoxyribose-3-(2-cyanoethyl N,N-diisopropylphosphoramidite)

Refernces