ethyl (1S,2S)-1-<<(benzyloxy)carbonyl>amino>-2-(mesyloxy)-6-methoxy-7-methyl-2,3,5,8-tetrahydro-5,8-dioxo-1H-pyrrolo<1,2-a>indole-9-carboxylate

Base Information

Chemical Name:ethyl (1S,2S)-1-<<(benzyloxy)carbonyl>amino>-2-(mesyloxy)-6-methoxy-7-methyl-2,3,5,8-tetrahydro-5,8-dioxo-1H-pyrrolo<1,2-a>indole-9-carboxylate
CAS No.:98777-47-0
Molecular Formula:C₂₅H₂₆N₂O₁₀S
Molecular Weight:546.555
Hs Code.:

Synonyms:ethyl (1S,2S)-1-<<(benzyloxy)carbonyl>amino>-2-(mesyloxy)-6-methoxy-7-methyl-2,3,5,8-tetrahydro-5,8-dioxo-1H-pyrrolo<1,2-a>indole-9-carboxylate

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Chemical Property of ethyl (1S,2S)-1-<<(benzyloxy)carbonyl>amino>-2-(mesyloxy)-6-methoxy-7-methyl-2,3,5,8-tetrahydro-5,8-dioxo-1H-pyrrolo<1,2-a>indole-9-carboxylate

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Technology Process of ethyl (1S,2S)-1-<<(benzyloxy)carbonyl>amino>-2-(mesyloxy)-6-methoxy-7-methyl-2,3,5,8-tetrahydro-5,8-dioxo-1H-pyrrolo<1,2-a>indole-9-carboxylate

There total 12 articles about ethyl (1S,2S)-1-<<(benzyloxy)carbonyl>amino>-2-(mesyloxy)-6-methoxy-7-methyl-2,3,5,8-tetrahydro-5,8-dioxo-1H-pyrrolo<1,2-a>indole-9-carboxylate 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: 91.0%

: 124-63-0
methanesulfonyl chloride

: 98777-46-9
ethyl (1S,2S)-1-<<(benzyloxy)carbonyl>amino>-2-hydroxy-6-methoxy-7-methyl-2,3,5,8-tetrahydro-5,8-dioxo-1H-pyrrolo<1,2-a>indole-9-carboxylate

: 98777-47-0
ethyl (1S,2S)-1-<<(benzyloxy)carbonyl>amino>-2-(mesyloxy)-6-methoxy-7-methyl-2,3,5,8-tetrahydro-5,8-dioxo-1H-pyrrolo<1,2-a>indole-9-carboxylate

Guidance literature:: With TEA; In dichloromethane; for 1h; Ambient temperature;
DOI:10.1021/jo00223a019

Reference yield:

: 98854-91-2
N-<(benzyloxy)carbonyl>-D-vinylglycine methyl ester

: 98777-47-0
ethyl (1S,2S)-1-<<(benzyloxy)carbonyl>amino>-2-(mesyloxy)-6-methoxy-7-methyl-2,3,5,8-tetrahydro-5,8-dioxo-1H-pyrrolo<1,2-a>indole-9-carboxylate

Guidance literature:: Multi-step reaction with 11 steps

1: 62 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 82 h

2: 91 percent / sodium azide, ammonium chloride / methanol / 2 h / Heating

3: 82 percent / imidazole / dimethylformamide / 70 h / Ambient temperature

4: 100 percent / LiOH / dioxane / 4 h / Ambient temperature

5: tetrahydrofuran / 18 h

6: 1.) isopropyl magnesium bromide / 1.) a) THF, 0 deg C, 10 min, b) RT, 75 min, c) 40 deg C, 15 min, 2.) THF, RT, 21 h

7: 48 percent / H₂ / PtO₂ / ethanol / 12 h

8: SiO₂ / CHCl₃ / 28 h

9: cupric bromide, potassium carbonate / acetonitrile / 16 h / 50 °C

10: 100 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / -48 °C

11: 91 percent / TEA / CH₂Cl₂ / 1 h / Ambient temperature

With 1H-imidazole; lithium hydroxide; sodium azide; TEA; ammonium chloride; tetrabutyl ammonium fluoride; hydrogen; isopropylmagnesium bromide; silica gel; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; copper(ll) bromide; platinum(IV) oxide; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; chloroform; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo00223a019

Reference yield:

: [(1R,2S)-3-Azido-2-(tert-butyl-dimethyl-silanyloxy)-1-(imidazole-1-carbonyl)-propyl]-carbamic acid benzyl ester

: 98777-47-0
ethyl (1S,2S)-1-<<(benzyloxy)carbonyl>amino>-2-(mesyloxy)-6-methoxy-7-methyl-2,3,5,8-tetrahydro-5,8-dioxo-1H-pyrrolo<1,2-a>indole-9-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) isopropyl magnesium bromide / 1.) a) THF, 0 deg C, 10 min, b) RT, 75 min, c) 40 deg C, 15 min, 2.) THF, RT, 21 h

2: 48 percent / H₂ / PtO₂ / ethanol / 12 h

3: SiO₂ / CHCl₃ / 28 h

4: cupric bromide, potassium carbonate / acetonitrile / 16 h / 50 °C

5: 100 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / -48 °C

6: 91 percent / TEA / CH₂Cl₂ / 1 h / Ambient temperature

With TEA; tetrabutyl ammonium fluoride; hydrogen; isopropylmagnesium bromide; silica gel; potassium carbonate; copper(ll) bromide; platinum(IV) oxide; In tetrahydrofuran; ethanol; dichloromethane; chloroform; acetonitrile;
DOI:10.1021/jo00223a019