1-(3'-O-benzoyl-4'O-[(4,4'-dimethoxytriphenyl)methyl]-β-D-ribopyranosyl)-3-(N-phthaloyl-2-aminoethyl)indole

Base Information

Chemical Name:1-(3'-O-benzoyl-4'O-[(4,4'-dimethoxytriphenyl)methyl]-β-D-ribopyranosyl)-3-(N-phthaloyl-2-aminoethyl)indole
CAS No.:221170-36-1
Molecular Formula:C₅₁H₄₄N₂O₉
Molecular Weight:828.918
Hs Code.:

Synonyms:1-(3'-O-benzoyl-4'O-[(4,4'-dimethoxytriphenyl)methyl]-β-D-ribopyranosyl)-3-(N-phthaloyl-2-aminoethyl)indole

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Chemical Property of 1-(3'-O-benzoyl-4'O-[(4,4'-dimethoxytriphenyl)methyl]-β-D-ribopyranosyl)-3-(N-phthaloyl-2-aminoethyl)indole

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Technology Process of 1-(3'-O-benzoyl-4'O-[(4,4'-dimethoxytriphenyl)methyl]-β-D-ribopyranosyl)-3-(N-phthaloyl-2-aminoethyl)indole

There total 10 articles about 1-(3'-O-benzoyl-4'O-[(4,4'-dimethoxytriphenyl)methyl]-β-D-ribopyranosyl)-3-(N-phthaloyl-2-aminoethyl)indole 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: 42.0%

: 40615-36-9
4,4'-dimethoxytrityl chloride

: 221170-35-0
1-(2'-O-benzoyl-β-D-ribopyranosyl)-3-(N-phthaloyl-2-aminoethyl)indole

: 221170-36-1
1-(3'-O-benzoyl-4'O-[(4,4'-dimethoxytriphenyl)methyl]-β-D-ribopyranosyl)-3-(N-phthaloyl-2-aminoethyl)indole

Guidance literature:: 1-(2'-O-benzoyl-β-D-ribopyranosyl)-3-(N-phthaloyl-2-aminoethyl)indole; With dmap; 4 A molecular sieve; N-ethyl-N,N-diisopropylamine; In pyridine; dichloromethane; for 0.5h;

4,4'-dimethoxytrityl chloride; In pyridine; dichloromethane; at 0 ℃; for 7.25h;

With propan-1-ol; dmap; 4-nitro-phenol; N-ethyl-N,N-diisopropylamine; In pyridine; at 75 - 80 ℃; for 96h;

Reference yield:

: Benzoic acid (2R,3R,4R,5R)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-2-{3-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethyl]-indol-1-yl}-4-hydroxy-tetrahydro-pyran-3-yl ester

: 221170-36-1
1-(3'-O-benzoyl-4'O-[(4,4'-dimethoxytriphenyl)methyl]-β-D-ribopyranosyl)-3-(N-phthaloyl-2-aminoethyl)indole

Guidance literature:: With pyridine; dmap; 4-nitro-phenol; N-ethyl-N,N-diisopropylamine; In propan-1-ol; at 75 - 80 ℃; for 96h; Yield given;
DOI:10.1055/s-1999-3112

Reference yield:

: 15741-71-6
N-phthalimidotryptamine

: 221170-36-1
1-(3'-O-benzoyl-4'O-[(4,4'-dimethoxytriphenyl)methyl]-β-D-ribopyranosyl)-3-(N-phthaloyl-2-aminoethyl)indole

Guidance literature:: Multi-step reaction with 8 steps

1: 86 percent / BH₃*THF, CF₃COOH / 0.5 h / 0 °C

2: ethanol / 4 h / Heating

3: pyridine / 18 h / Ambient temperature

4: DDQ / CH₂Cl₂ / 1.5 h / Ambient temperature

5: 76 percent / MeONa / methanol / 18 h / Ambient temperature

6: 64 percent / DMAP, pyridine / CH₂Cl₂ / 0.25 h / -78 °C

7: DMAP, pyridine, DIPEA, molecular sieves / CH₂Cl₂ / 4.25 h / Ambient temperature

8: DMAP, pyridine, DIPEA, p-nitrophenol / propan-1-ol / 96 h / 75 - 80 °C

With pyridine; dmap; 4-nitro-phenol; molecular sieve; borane-THF; sodium methylate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In methanol; propan-1-ol; ethanol; dichloromethane;
DOI:10.1055/s-1999-3112