(R)-2-benzyloxycarbonylamino-3-(1H-indol-3-yl)propionic acid allyl ester

Base Information

Chemical Name:(R)-2-benzyloxycarbonylamino-3-(1H-indol-3-yl)propionic acid allyl ester
CAS No.:346440-85-5
Molecular Formula:C₂₂H₂₂N₂O₄
Molecular Weight:378.428
Hs Code.:

Synonyms:(R)-2-benzyloxycarbonylamino-3-(1H-indol-3-yl)propionic acid allyl ester

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Chemical Property of (R)-2-benzyloxycarbonylamino-3-(1H-indol-3-yl)propionic acid allyl ester

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Technology Process of (R)-2-benzyloxycarbonylamino-3-(1H-indol-3-yl)propionic acid allyl ester

There total 1 articles about (R)-2-benzyloxycarbonylamino-3-(1H-indol-3-yl)propionic acid allyl 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: 89.0%

: 107-18-6
allyl alcohol

: 2279-15-4
N-(benzyloxycarbonyl)-D-tryptophan

: 346440-85-5
(R)-2-benzyloxycarbonylamino-3-(1H-indol-3-yl)propionic acid allyl ester

Guidance literature:: N-(benzyloxycarbonyl)-D-tryptophan; With dmap; dicyclohexyl-carbodiimide; In dichloromethane; for 0.166667h;

allyl alcohol; In dichloromethane; for 0.5h; Further stages.;
DOI:10.1021/jm010825z

Reference yield: 52.0%

: 346440-85-5
(R)-2-benzyloxycarbonylamino-3-(1H-indol-3-yl)propionic acid allyl ester

: 354117-18-3
(2R,3aS,8aS)-3,3a,8,8a-tetrahydro-2H-pyrrolo[2,3-b]indole-1,2-dicarboxylic acid 2-allyl ester 1-benzyl ester

Guidance literature:: With trifluoroacetic acid; at 20 ℃; for 3h;
DOI:10.1021/jm010825z

Reference yield:

: 346440-85-5
(R)-2-benzyloxycarbonylamino-3-(1H-indol-3-yl)propionic acid allyl ester

: 354117-36-5
(R)-2-amino-2-(1H-indol-3-ylmethyl)-4-methyl-pent-4-anoic acid ((S)-1-phenylethyl)-amide

Guidance literature:: Multi-step reaction with 7 steps

1.1: 52 percent / TFA / 3 h / 20 °C

2.1: 86 percent / aq. Na₂CO₃ / dioxane / 16 h / 20 °C

3.1: LHMDS; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / tetrahydrofuran / 2 h / -78 °C

3.2: 21 percent / tetrahydrofuran / -78 - 20 °C

4.1: 79 percent / TFA / CH₂Cl₂ / 24 h / 20 °C

5.1: 100 percent / Pd(PPh₃)4; morpholine / tetrahydrofuran / 0.5 h / 20 °C

6.1: HBTU; DIPEA / dimethylformamide / 0.17 h / 20 °C

6.2: 74 percent / DIPEA / dimethylformamide / 8 h

7.1: 98 percent / H₂ / 10percent Pd(OH)2/C / methanol / 1.5 h / 30 °C / 2585.81 Torr

With morpholine; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; tetrakis(triphenylphosphine) palladium⁽⁰⁾; hydrogen; sodium carbonate; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; lithium hexamethyldisilazane; 10percent Pd(OH)2/C; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jm010825z