benzyl ((1S,2S,3'S,5R)-1'-methoxy-2'-oxo-8-propionyl-6-oxaspiro[bicyclo[3.2.2]non[8]ene-4,3'-indolin]-2-yl)carbamate

Base Information

Chemical Name:benzyl ((1S,2S,3'S,5R)-1'-methoxy-2'-oxo-8-propionyl-6-oxaspiro[bicyclo[3.2.2]non[8]ene-4,3'-indolin]-2-yl)carbamate
CAS No.:1341221-99-5
Molecular Formula:C₂₇H₂₈N₂O₆
Molecular Weight:476.529
Hs Code.:

Synonyms:benzyl ((1S,2S,3'S,5R)-1'-methoxy-2'-oxo-8-propionyl-6-oxaspiro[bicyclo[3.2.2]non[8]ene-4,3'-indolin]-2-yl)carbamate

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Chemical Property of benzyl ((1S,2S,3'S,5R)-1'-methoxy-2'-oxo-8-propionyl-6-oxaspiro[bicyclo[3.2.2]non[8]ene-4,3'-indolin]-2-yl)carbamate

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Technology Process of benzyl ((1S,2S,3'S,5R)-1'-methoxy-2'-oxo-8-propionyl-6-oxaspiro[bicyclo[3.2.2]non[8]ene-4,3'-indolin]-2-yl)carbamate

There total 15 articles about benzyl ((1S,2S,3'S,5R)-1'-methoxy-2'-oxo-8-propionyl-6-oxaspiro[bicyclo[3.2.2]non[8]ene-4,3'-indolin]-2-yl)carbamate 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:

: C₂₇H₃₀N₂O₆

: 1341221-99-5
benzyl ((1S,2S,3'S,5R)-1'-methoxy-2'-oxo-8-propionyl-6-oxaspiro[bicyclo[3.2.2]non[8]ene-4,3'-indolin]-2-yl)carbamate

Guidance literature:: With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In dimethyl sulfoxide; at 20 - 50 ℃; for 1.5h;
DOI:10.1021/ja208617c

Reference yield:

: 1397715-56-8
C₂₅H₃₃NO₆Si

: 1341221-99-5
benzyl ((1S,2S,3'S,5R)-1'-methoxy-2'-oxo-8-propionyl-6-oxaspiro[bicyclo[3.2.2]non[8]ene-4,3'-indolin]-2-yl)carbamate

Guidance literature:: Multi-step reaction with 13 steps

1.1: toluene / 2.33 h / 70 °C / Inert atmosphere

1.2: 20 °C / Inert atmosphere

2.1: sodium hydride / methanol; mineral oil / 0 - 20 °C / Inert atmosphere

3.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane / 3 h / 20 °C

4.1: trimethylsilyl cyanide; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

4.2: 4 h / 0 °C / Inert atmosphere

5.1: pyrrolidine; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / acetonitrile / 3 h / 0 - 20 °C / Inert atmosphere

5.2: 20 °C

5.3: pH 1

6.1: oxalyl dichloride / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

7.1: sodium azide / water; toluene / 0.17 h / 0 °C

8.1: toluene / 0.5 h / 80 °C / Inert atmosphere

9.1: toluene / 2 h / 70 °C / Inert atmosphere

10.1: oxalyl dichloride; N,N-dimethyl-formamide / 0 - 70 °C / Inert atmosphere

11.1: triethylsilane; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine / N,N-dimethyl-formamide / 4.5 h / 80 °C / Inert atmosphere

12.1: tetrahydrofuran; diethyl ether / 1.75 h / -78 °C / Inert atmosphere

13.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 1.5 h / 20 - 50 °C

With pyrrolidine; triethylsilane; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium azide; oxalyl dichloride; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; trimethylsilyl cyanide; [bis(acetoxy)iodo]benzene; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N,N-dimethyl-formamide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; acetonitrile; mineral oil; 8.1: Curtius rearrangement;
DOI:10.1021/ja208617c

Reference yield:

: 1341221-81-5
(1S,3'S,5S)-1'-methoxy-2',9-dioxo-6-oxaspiro[bicyclo[3.2.2]non[2]ene-4,3'-indoline]-2-carbaldehyde

: 1341221-99-5
benzyl ((1S,2S,3'S,5R)-1'-methoxy-2'-oxo-8-propionyl-6-oxaspiro[bicyclo[3.2.2]non[8]ene-4,3'-indolin]-2-yl)carbamate

Guidance literature:: Multi-step reaction with 10 steps

1.1: trimethylsilyl cyanide; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

1.2: 4 h / 0 °C / Inert atmosphere

2.1: pyrrolidine; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / acetonitrile / 3 h / 0 - 20 °C / Inert atmosphere

2.2: 20 °C

2.3: pH 1

3.1: oxalyl dichloride / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

4.1: sodium azide / water; toluene / 0.17 h / 0 °C

5.1: toluene / 0.5 h / 80 °C / Inert atmosphere

6.1: toluene / 2 h / 70 °C / Inert atmosphere

7.1: oxalyl dichloride; N,N-dimethyl-formamide / 0 - 70 °C / Inert atmosphere

8.1: triethylsilane; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine / N,N-dimethyl-formamide / 4.5 h / 80 °C / Inert atmosphere

9.1: tetrahydrofuran; diethyl ether / 1.75 h / -78 °C / Inert atmosphere

10.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 1.5 h / 20 - 50 °C

With pyrrolidine; triethylsilane; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium azide; oxalyl dichloride; trimethylsilyl cyanide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N,N-dimethyl-formamide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; diethyl ether; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; acetonitrile; 5.1: Curtius rearrangement;
DOI:10.1021/ja208617c