3-((2R,4S,5R)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)-methyl)-4-hydroxytetrahydrofuran-2-yl)-3,9-dihydro-2H-pyrimido-[4,5-b]indol-2-one

Base Information

• Chemical Name: 3-((2R,4S,5R)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)-methyl)-4-hydroxytetrahydrofuran-2-yl)-3,9-dihydro-2H-pyrimido-[4,5-b]indol-2-one
• CAS No.: 169243-52-1
• Molecular Formula: C₃₆H₃₃N₃O₆
• Molecular Weight: 603.675
• Mol file: 169243-52-1.mol

Synonyms:3-((2R,4S,5R)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)-methyl)-4-hydroxytetrahydrofuran-2-yl)-3,9-dihydro-2H-pyrimido-[4,5-b]indol-2-one

Chemical Property of 3-((2R,4S,5R)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)-methyl)-4-hydroxytetrahydrofuran-2-yl)-3,9-dihydro-2H-pyrimido-[4,5-b]indol-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-((2R,4S,5R)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)-methyl)-4-hydroxytetrahydrofuran-2-yl)-3,9-dihydro-2H-pyrimido-[4,5-b]indol-2-one

There total 14 articles about 3-((2R,4S,5R)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)-methyl)-4-hydroxytetrahydrofuran-2-yl)-3,9-dihydro-2H-pyrimido-[4,5-b]indol-2-one 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: 100.0%

4,4'-dimethoxytrityl chloride (40615-36-9) + 3-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-3,9-dihydro-2H-pyrimido[4,5-b]indol-2-one → 3-((2R,4S,5R)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)-methyl)-4-hydroxytetrahydrofuran-2-yl)-3,9-dihydro-2H-pyrimido-[4,5-b]indol-2-one (169243-52-1)

Guidance literature:

With pyridine; dmap; In toluene; for 12h;

DOI:10.1021/acs.joc.1c01176

Reference yield:

3-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-2-oxo-2,3-dihydro-pyrimido[4,5-b]indole-9-carboxylic acid tert-butyl ester → 3-((2R,4S,5R)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)-methyl)-4-hydroxytetrahydrofuran-2-yl)-3,9-dihydro-2H-pyrimido-[4,5-b]indol-2-one (169243-52-1)

Guidance literature:

With tert-butylamine; In methanol; at 20 ℃; Yield given;

DOI:10.1016/0040-4039(96)01016-7

Reference yield:

tert-butyl(5-bromo-1-((2R,4S,5R)-4-((tert-butyldiphenylsilyl)oxy)-5-(((tert-butyldiphenylsilyl)oxy)methyl)tetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)(phenyl)carbamate → 3-((2R,4S,5R)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)-methyl)-4-hydroxytetrahydrofuran-2-yl)-3,9-dihydro-2H-pyrimido-[4,5-b]indol-2-one (169243-52-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium acetate; C₃₆H₃₄Cl₂P₂Pd / dimethyl amine / 12 h / 150 °C

1.2: 3 h / 22 °C

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 22 °C

2.2: Dowex-50 / 1 h

3.1: dmap; pyridine / toluene / 12 h

With pyridine; dmap; tetrabutyl ammonium fluoride; sodium acetate; C₃₆H₃₄Cl₂P₂Pd; In tetrahydrofuran; dimethyl amine; toluene;

DOI:10.1021/acs.joc.1c01176

upstream raw materials:

4,4'-dimethoxytrityl chloride

5-Iodo-2'-deoxyuridine

N-tert-butoxycarbonyl-2-trimethylstannylaniline

{2-[1-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-phenyl}-carbamic acid tert-butyl ester