(2S,3aS,7aR)-7a-[3-(N-benzyloxycarbonyl-N'-tert-butoxycarbonylamino)-3-methoxycarbonyl-allyl]-octahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester

Base Information

Chemical Name:(2S,3aS,7aR)-7a-[3-(N-benzyloxycarbonyl-N'-tert-butoxycarbonylamino)-3-methoxycarbonyl-allyl]-octahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester
CAS No.:365973-31-5
Molecular Formula:C₃₉H₅₀N₂O₁₀
Molecular Weight:706.833
Hs Code.:

(2S,3aS,7aR)-7a-[3-(N-benzyloxycarbonyl-N'-tert-butoxycarbonylamino)-3-methoxycarbonyl-allyl]-octahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester

Synonyms:(2S,3aS,7aR)-7a-[3-(N-benzyloxycarbonyl-N'-tert-butoxycarbonylamino)-3-methoxycarbonyl-allyl]-octahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester

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Chemical Property of (2S,3aS,7aR)-7a-[3-(N-benzyloxycarbonyl-N'-tert-butoxycarbonylamino)-3-methoxycarbonyl-allyl]-octahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester

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Technology Process of (2S,3aS,7aR)-7a-[3-(N-benzyloxycarbonyl-N'-tert-butoxycarbonylamino)-3-methoxycarbonyl-allyl]-octahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester

There total 17 articles about (2S,3aS,7aR)-7a-[3-(N-benzyloxycarbonyl-N'-tert-butoxycarbonylamino)-3-methoxycarbonyl-allyl]-octahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl 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: 88.0%

: 24424-99-5
di-tert-butyl dicarbonate

: (2S,3aS,7aR)-7a-(3-benzyloxycarbonylamino-3-methoxycarbonyl-allyl)-octahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester

: 365973-31-5
(2S,3aS,7aR)-7a-[3-(N-benzyloxycarbonyl-N'-tert-butoxycarbonylamino)-3-methoxycarbonyl-allyl]-octahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester

Guidance literature:: With dmap; In tetrahydrofuran; for 2h;
DOI:10.1016/S0040-4020(01)00538-5

Reference yield:

: 365973-11-1
(2S,4S)-4-Allyl-5-oxo-pyrrolidine-2-carboxylic acid methyl ester

: 365973-31-5
(2S,3aS,7aR)-7a-[3-(N-benzyloxycarbonyl-N'-tert-butoxycarbonylamino)-3-methoxycarbonyl-allyl]-octahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester

Guidance literature:: Multi-step reaction with 14 steps

1.1: 98 percent / DMAP / tetrahydrofuran / 2 h / 20 °C

2.1: 91 percent / lithium triethylborohydride / tetrahydrofuran / 1 h / -78 °C

3.1: 19 percent / tert-butyldimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 0.67 h / -78 °C

4.1: 89 percent / benzylidene-bis(tricyclohexylphosphine)dichlororuthenium / CH₂Cl₂ / 0.5 h / 20 °C

5.1: 94 percent / H₂ / Pd/C / ethanol / 30 h / 1520 Torr

6.1: 84 percent / NaHCO₃ / acetonitrile; methanol / Electrolysis

7.1: 97 percent / BF₃*Et₂O / CH₂Cl₂ / -78 - -20 °C

8.1: 89 percent / CF₃COOH / CH₂Cl₂ / 1 h / 20 °C

9.1: 99 percent / KHCO₃ / ethyl acetate; H₂O / 2 h

10.1: 100 percent / aq. LiOH / dioxane / 48 h / 50 °C

11.1: 92 percent / benzene / 3 h / Heating

12.1: OsCl₃; Me₃NO*2H₂O / acetone; H₂O / 2 h / 20 °C

12.2: 93 percent / NaIO₄ / acetone; H₂O / 2 h / 20 °C

13.1: t-BuOK / CH₂Cl₂ / 0.5 h / -78 °C

13.2: 85 percent / CH₂Cl₂ / -78 - 20 °C

14.1: 88 percent / DMAP / tetrahydrofuran / 2 h

With dmap; lithium hydroxide; Grubbs catalyst first generation; osmium (III) chloride; trimethylamine-N-oxide; boron trifluoride diethyl etherate; t-butyldimethylsiyl triflate; potassium tert-butylate; hydrogen; lithium triethylborohydride; sodium hydrogencarbonate; potassium hydrogencarbonate; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; ethyl acetate; acetone; acetonitrile; benzene;
DOI:10.1016/S0040-4020(01)00538-5

Reference yield:

: 213475-89-9
(2S,4S)-2-allyl-4-tert-butoxycarbonylamino-pentanedioic acid dimethyl ester

: 365973-31-5
(2S,3aS,7aR)-7a-[3-(N-benzyloxycarbonyl-N'-tert-butoxycarbonylamino)-3-methoxycarbonyl-allyl]-octahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester

Guidance literature:: Multi-step reaction with 15 steps

1.1: TFA / CH₂Cl₂ / 1.5 h / 0 °C

1.2: 85 percent / toluene / 0.67 h / 110 °C

2.1: 98 percent / DMAP / tetrahydrofuran / 2 h / 20 °C

3.1: 91 percent / lithium triethylborohydride / tetrahydrofuran / 1 h / -78 °C

4.1: 19 percent / tert-butyldimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 0.67 h / -78 °C

5.1: 89 percent / benzylidene-bis(tricyclohexylphosphine)dichlororuthenium / CH₂Cl₂ / 0.5 h / 20 °C

6.1: 94 percent / H₂ / Pd/C / ethanol / 30 h / 1520 Torr

7.1: 84 percent / NaHCO₃ / acetonitrile; methanol / Electrolysis

8.1: 97 percent / BF₃*Et₂O / CH₂Cl₂ / -78 - -20 °C

9.1: 89 percent / CF₃COOH / CH₂Cl₂ / 1 h / 20 °C

10.1: 99 percent / KHCO₃ / ethyl acetate; H₂O / 2 h

11.1: 100 percent / aq. LiOH / dioxane / 48 h / 50 °C

12.1: 92 percent / benzene / 3 h / Heating

13.1: OsCl₃; Me₃NO*2H₂O / acetone; H₂O / 2 h / 20 °C

13.2: 93 percent / NaIO₄ / acetone; H₂O / 2 h / 20 °C

14.1: t-BuOK / CH₂Cl₂ / 0.5 h / -78 °C

14.2: 85 percent / CH₂Cl₂ / -78 - 20 °C

15.1: 88 percent / DMAP / tetrahydrofuran / 2 h

With dmap; lithium hydroxide; Grubbs catalyst first generation; osmium (III) chloride; trimethylamine-N-oxide; boron trifluoride diethyl etherate; t-butyldimethylsiyl triflate; potassium tert-butylate; hydrogen; lithium triethylborohydride; sodium hydrogencarbonate; potassium hydrogencarbonate; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; ethyl acetate; acetone; acetonitrile; benzene;
DOI:10.1016/S0040-4020(01)00538-5