Benzyl N-<(5aRS,6aSR,9aRS)-4,5a-bis(diethoxymethyl)-4,5,5a,6,6a,7,8,9a-octahydro-5,8-dioxo-oxazolo<4',5':1,2>benz<5,4,3-c,d>indol-7-yl>carbamate

Base Information

• Chemical Name: Benzyl N-<(5aRS,6aSR,9aRS)-4,5a-bis(diethoxymethyl)-4,5,5a,6,6a,7,8,9a-octahydro-5,8-dioxo-oxazolo<4',5':1,2>benz<5,4,3-c,d>indol-7-yl>carbamate
• CAS No.: 138206-91-4
• Molecular Formula: C₃₀H₃₇N₃O₉
• Molecular Weight: 583.638
• Mol file: 138206-91-4.mol

Synonyms:Benzyl N-<(5aRS,6aSR,9aRS)-4,5a-bis(diethoxymethyl)-4,5,5a,6,6a,7,8,9a-octahydro-5,8-dioxo-oxazolo<4',5':1,2>benz<5,4,3-c,d>indol-7-yl>carbamate

Chemical Property of Benzyl N-<(5aRS,6aSR,9aRS)-4,5a-bis(diethoxymethyl)-4,5,5a,6,6a,7,8,9a-octahydro-5,8-dioxo-oxazolo<4',5':1,2>benz<5,4,3-c,d>indol-7-yl>carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzyl N-<(5aRS,6aSR,9aRS)-4,5a-bis(diethoxymethyl)-4,5,5a,6,6a,7,8,9a-octahydro-5,8-dioxo-oxazolo<4',5':1,2>benz<5,4,3-c,d>indol-7-yl>carbamate

There total 8 articles about Benzyl N-<(5aRS,6aSR,9aRS)-4,5a-bis(diethoxymethyl)-4,5,5a,6,6a,7,8,9a-octahydro-5,8-dioxo-oxazolo<4',5':1,2>benz<5,4,3-c,d>indol-7-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: 80.0%

Dibenzyl 1-<(2aRS,4SR)-1,2a-bis(diethoxymethyl)-1,2,2a,3,4,5-hexahydro-2,5-dioxobenzindol-4-yl>-1,2-hydrazine dicarboxylate (138206-99-2) → Benzyl N-<(5aRS,6aSR,9aRS)-4,5a-bis(diethoxymethyl)-4,5,5a,6,6a,7,8,9a-octahydro-5,8-dioxo-oxazolo<4',5':1,2>benz<5,4,3-c,d>indol-7-yl>carbamate (138206-91-4)

Guidance literature:

With lithium triethylborohydride; In tetrahydrofuran; 1) -78 deg C 2) r.t.;

DOI:10.1016/S0040-4039(00)79428-7

Reference yield: 2.0%

Dibenzyl 1-<(2aRS,4SR)-1,2a-bis(diethoxymethyl)-1,2,2a,3,4,5-hexahydro-2,5-dioxobenzindol-4-yl>-1,2-hydrazine dicarboxylate (138206-99-2) → Benzyl N-<(5aRS,6aSR,9aRS)-4,5a-bis(diethoxymethyl)-4,5,5a,6,6a,7,8,9a-octahydro-5,8-dioxo-oxazolo<4',5':1,2>benz<5,4,3-c,d>indol-7-yl>carbamate (138206-91-4) + Dibenzyl 1-<(2aRS,4SR,5SR)-1,2a-bis(diethoxymethyl)-1,2,2a,3,4,5-hexahydro-5-hydroxy-2-oxobenzindol-4-yl>-1,2-hydrazine dicarboxylate

Guidance literature:

With lithium triethylborohydride; In tetrahydrofuran; 1.) -78 deg C, 1.5 h, 2.) room temp., 1 h;

DOI:10.1002/ardp.19953280708

Reference yield:

(+/-)-5-Bromo-1,2,2a,3,4,5-hexahydro-2-oxobenzindole-1,2a-dicarbaldehyde tetraethylacetal → Benzyl N-<(5aRS,6aSR,9aRS)-4,5a-bis(diethoxymethyl)-4,5,5a,6,6a,7,8,9a-octahydro-5,8-dioxo-oxazolo<4',5':1,2>benz<5,4,3-c,d>indol-7-yl>carbamate (138206-91-4)

Guidance literature:

Multi-step reaction with 3 steps

1: Et₃N, DMSO / CCl₄ / 4 h / Ambient temperature

2: 75 percent / LDA / tetrahydrofuran; hexane / 1.) -78 deg C, 1 h, 2.) 3 min

3: 80 percent / LiBH(Et)3 / tetrahydrofuran / 1.) -78 deg C, 1.5 h, 2.) room temp., 1 h

With lithium triethylborohydride; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; tetrachloromethane; hexane;

DOI:10.1002/ardp.19953280708

upstream raw materials:

Dibenzyl 1-<(2aRS,4SR)-1,2a-bis(diethoxymethyl)-1,2,2a,3,4,5-hexahydro-2,5-dioxobenzindol-4-yl>-1,2-hydrazine dicarboxylate

dibenzyl azodicarboxylate

(+/-)-1,2,2a,3,4,5-Hexahydro-2,5-dioxobenzindole-1,2a-dicarbaldehyde tetraethylacetal

(RS)-2a,3,4,5-tetrahydro-1H-benz[cd]indol-2-one