3-{6-benzyloxy-4-[2-tert-butoxycarbonylamino-3-(1H-indol-3-yl)-propionyloxy]-chroman-3-ylmethyl}-4-methoxy-benzoic acid methyl ester

Base Information

Chemical Name:3-{6-benzyloxy-4-[2-tert-butoxycarbonylamino-3-(1H-indol-3-yl)-propionyloxy]-chroman-3-ylmethyl}-4-methoxy-benzoic acid methyl ester
CAS No.:251639-70-0
Molecular Formula:C₄₂H₄₄N₂O₉
Molecular Weight:720.819
Hs Code.:

3-{6-benzyloxy-4-[2-<i>tert</i>-butoxycarbonylamino-3-(1<i>H</i>-indol-3-yl)-propionyloxy]-chroman-3-ylmethyl}-4-methoxy-benzoic acid methyl ester

Synonyms:3-{6-benzyloxy-4-[2-tert-butoxycarbonylamino-3-(1H-indol-3-yl)-propionyloxy]-chroman-3-ylmethyl}-4-methoxy-benzoic acid methyl ester

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Chemical Property of 3-{6-benzyloxy-4-[2-tert-butoxycarbonylamino-3-(1H-indol-3-yl)-propionyloxy]-chroman-3-ylmethyl}-4-methoxy-benzoic acid methyl ester

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Technology Process of 3-{6-benzyloxy-4-[2-tert-butoxycarbonylamino-3-(1H-indol-3-yl)-propionyloxy]-chroman-3-ylmethyl}-4-methoxy-benzoic acid methyl ester

There total 6 articles about 3-{6-benzyloxy-4-[2-tert-butoxycarbonylamino-3-(1H-indol-3-yl)-propionyloxy]-chroman-3-ylmethyl}-4-methoxy-benzoic acid methyl ester 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: 46.0%

: 5241-64-5
Boc-D-Trp-OH

: 3-((3R,4R)-6-Benzyloxy-4-hydroxy-chroman-3-ylmethyl)-4-methoxy-benzoic acid methyl ester

: 251639-70-0
3-{6-benzyloxy-4-[2-tert-butoxycarbonylamino-3-(1H-indol-3-yl)-propionyloxy]-chroman-3-ylmethyl}-4-methoxy-benzoic acid methyl ester

Guidance literature:: With dmap; diethylcarbamazine; In dichloromethane;
DOI:10.1016/S0960-894X(99)00461-8

Reference yield:

: 80096-64-6
6-hydroxy-2,3-dihydro-4H-chromen-4-one

: 251639-70-0
3-{6-benzyloxy-4-[2-tert-butoxycarbonylamino-3-(1H-indol-3-yl)-propionyloxy]-chroman-3-ylmethyl}-4-methoxy-benzoic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 88 percent / K₂CO₃ / acetone

2: 80 percent / pyrrolidine / methanol

3: 57 percent / H₂ / Pd/C / ethyl acetate / 517.15 Torr

4: 80 percent / NaBH₄; CeCl₃ / methanol; tetrahydrofuran

5: 46 percent / DEC; DMAP / CH₂Cl₂

With pyrrolidine; dmap; sodium tetrahydroborate; cerium(III) chloride; diethylcarbamazine; hydrogen; potassium carbonate; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; acetone; 1: Alkylation / 2: Condensation / 3: Catalytic hydrogenation / 4: Reduction / 5: Esterification;
DOI:10.1016/S0960-894X(99)00461-8

Reference yield:

: 5802-17-5
6-methoxychroman-4-one

: 251639-70-0
3-{6-benzyloxy-4-[2-tert-butoxycarbonylamino-3-(1H-indol-3-yl)-propionyloxy]-chroman-3-ylmethyl}-4-methoxy-benzoic acid methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 93 percent / 48 percent aq. HBr; HOAc / Heating

2: 88 percent / K₂CO₃ / acetone

3: 80 percent / pyrrolidine / methanol

4: 57 percent / H₂ / Pd/C / ethyl acetate / 517.15 Torr

5: 80 percent / NaBH₄; CeCl₃ / methanol; tetrahydrofuran

6: 46 percent / DEC; DMAP / CH₂Cl₂

With pyrrolidine; dmap; sodium tetrahydroborate; cerium(III) chloride; diethylcarbamazine; hydrogen bromide; hydrogen; potassium carbonate; acetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; acetone; 1: demethylation / 2: Alkylation / 3: Condensation / 4: Catalytic hydrogenation / 5: Reduction / 6: Esterification;
DOI:10.1016/S0960-894X(99)00461-8