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Technology Process of methyl (1aS,8R,8aS,8bR)-1,1a,2,8,8a,8b-hexahydro-7-(benzyloxy)-8-(hydroxymethyl)-1-(tert-butyloxycarbonyl)azirino[2',3':3,4]pyrrolo[1,2-a]indole-5-carboxylate

methyl (1aS,8R,8aS,8bR)-1,1a,2,8,8a,8b-hexahydro-7-(benzyloxy)-8-(hydroxymethyl)-1-(tert-butyloxycarbonyl)azirino[2',3':3,4]pyrrolo[1,2-a]indole-5-carboxylate

Base Information
  • Chemical Name:methyl (1aS,8R,8aS,8bR)-1,1a,2,8,8a,8b-hexahydro-7-(benzyloxy)-8-(hydroxymethyl)-1-(tert-butyloxycarbonyl)azirino[2',3':3,4]pyrrolo[1,2-a]indole-5-carboxylate
  • CAS No.:187682-33-3
  • Molecular Formula:C26H30N2O6
  • Molecular Weight:466.534
  • Hs Code.:
methyl (1aS,8R,8aS,8bR)-1,1a,2,8,8a,8b-hexahydro-7-(benzyloxy)-8-(hydroxymethyl)-1-(tert-butyloxycarbonyl)azirino[2',3':3,4]pyrrolo[1,2-a]indole-5-carboxylate

Synonyms:methyl (1aS,8R,8aS,8bR)-1,1a,2,8,8a,8b-hexahydro-7-(benzyloxy)-8-(hydroxymethyl)-1-(tert-butyloxycarbonyl)azirino[2',3':3,4]pyrrolo[1,2-a]indole-5-carboxylate

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Chemical Property of methyl (1aS,8R,8aS,8bR)-1,1a,2,8,8a,8b-hexahydro-7-(benzyloxy)-8-(hydroxymethyl)-1-(tert-butyloxycarbonyl)azirino[2',3':3,4]pyrrolo[1,2-a]indole-5-carboxylate
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Technology Process of methyl (1aS,8R,8aS,8bR)-1,1a,2,8,8a,8b-hexahydro-7-(benzyloxy)-8-(hydroxymethyl)-1-(tert-butyloxycarbonyl)azirino[2',3':3,4]pyrrolo[1,2-a]indole-5-carboxylate

There total 21 articles about methyl (1aS,8R,8aS,8bR)-1,1a,2,8,8a,8b-hexahydro-7-(benzyloxy)-8-(hydroxymethyl)-1-(tert-butyloxycarbonyl)azirino[2',3':3,4]pyrrolo[1,2-a]indole-5-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: 94.0%

C<sub>26</sub>H<sub>28</sub>N<sub>2</sub>O<sub>5</sub>
1016976-26-3

C26H28N2O5

methyl (1aS,8R,8aS,8bR)-1,1a,2,8,8a,8b-hexahydro-7-(benzyloxy)-8-(hydroxymethyl)-1-(tert-butyloxycarbonyl)azirino[2',3':3,4]pyrrolo[1,2-a]indole-5-carboxylate
187682-33-3

methyl (1aS,8R,8aS,8bR)-1,1a,2,8,8a,8b-hexahydro-7-(benzyloxy)-8-(hydroxymethyl)-1-(tert-butyloxycarbonyl)azirino[2',3':3,4]pyrrolo[1,2-a]indole-5-carboxylate

Guidance literature:
C26H28N2O5; With 9-bora-bicyclo[3.3.1]nonane; In tetrahydrofuran; at 20 ℃; Inert atmosphere;
With sodium perborate tetrahydrate; In tetrahydrofuran; for 2h; aq. phosphate buffer;
DOI:10.1002/chem.201003489

Reference yield:

C<sub>32</sub>H<sub>44</sub>N<sub>2</sub>O<sub>6</sub>Si

C32H44N2O6Si

methyl (1aS,8R,8aS,8bR)-1,1a,2,8,8a,8b-hexahydro-7-(benzyloxy)-8-(hydroxymethyl)-1-(tert-butyloxycarbonyl)azirino[2',3':3,4]pyrrolo[1,2-a]indole-5-carboxylate
187682-33-3

methyl (1aS,8R,8aS,8bR)-1,1a,2,8,8a,8b-hexahydro-7-(benzyloxy)-8-(hydroxymethyl)-1-(tert-butyloxycarbonyl)azirino[2',3':3,4]pyrrolo[1,2-a]indole-5-carboxylate

methyl (1aS,8R,8aR,8bR)-1,1a,2,8,8a,8b-hexahydro-7-(benzyloxy)-8-(hydroxymethyl)-1-(tert-butyloxycarbonyl)azirino[2',3':3,4]pyrrolo[1,2-a]indole-5-carboxylate

methyl (1aS,8R,8aR,8bR)-1,1a,2,8,8a,8b-hexahydro-7-(benzyloxy)-8-(hydroxymethyl)-1-(tert-butyloxycarbonyl)azirino[2',3':3,4]pyrrolo[1,2-a]indole-5-carboxylate

Guidance literature:
With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 12h; Yield given. Yields of byproduct given; Ambient temperature;
DOI:10.1021/jo961992n

Reference yield:

(3S,4S)-4-N-phthalimido-1,5-hexadiene-3-ol
885703-19-5

(3S,4S)-4-N-phthalimido-1,5-hexadiene-3-ol

methyl (1aS,8R,8aS,8bR)-1,1a,2,8,8a,8b-hexahydro-7-(benzyloxy)-8-(hydroxymethyl)-1-(tert-butyloxycarbonyl)azirino[2',3':3,4]pyrrolo[1,2-a]indole-5-carboxylate
187682-33-3

methyl (1aS,8R,8aS,8bR)-1,1a,2,8,8a,8b-hexahydro-7-(benzyloxy)-8-(hydroxymethyl)-1-(tert-butyloxycarbonyl)azirino[2',3':3,4]pyrrolo[1,2-a]indole-5-carboxylate

Guidance literature:
Multi-step reaction with 16 steps
1.1: 1H-imidazole / N,N-dimethyl-formamide / 11 h / 20 °C / Inert atmosphere
2.1: osmium(VIII) oxide; (8a,9R,8′′′a,9′′′R)-9,9′-[(2,5-diphenylpyrimidine-4,6-diyl)bis(oxy)]bis(6′-methoxy-10,11-dihydrocinchonan); methanesulfonamide; sodium hydrogencarbonate; potassium carbonate; potassium hexacyanoferrate(III) / water; tert-butyl alcohol / 6 h / 5 °C / Inert atmosphere
3.1: nitrogen; methylamine / water / 1 h / 50 °C / 10 Torr / Inert atmosphere
4.1: sodium hydrogencarbonate / ethyl acetate / 1.5 h / Inert atmosphere
5.1: dmap; triethylamine; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.03 h / 0 - 20 °C / Inert atmosphere
6.1: dichloromethane / 1 h / -40 °C / Inert atmosphere
7.1: caesium carbonate / N,N-dimethyl-formamide / 4 h / 60 °C / Inert atmosphere
8.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 2 h / Inert atmosphere
9.1: Dess-Martin periodane / dichloromethane / 1.5 h / 20 °C / Inert atmosphere
10.1: acetic acid / chloroform / 12 h / 20 °C / Molecular sieve; Inert atmosphere
11.1: sodium cyanoborohydride / tetrahydrofuran / 2 h / Inert atmosphere
12.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere
13.1: dmap; potassium carbonate / dichloromethane / 20 °C / Inert atmosphere
14.1: 1,4-diaza-bicyclo[2.2.2]octane; bis(1,5-cyclooctadiene)diiridium(I) dichloride; (3,5-dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-(1-phenyl-ethyl)-amine / tetrahydrofuran / 20 °C / Inert atmosphere
15.1: palladium diacetate; silver nitrate; triphenylphosphine / 1,4-dioxane / 1 h / 80 °C / Inert atmosphere
16.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 20 °C / Inert atmosphere
16.2: 2 h / aq. phosphate buffer
With 1,4-diaza-bicyclo[2.2.2]octane; 1H-imidazole; dmap; osmium(VIII) oxide; bis(1,5-cyclooctadiene)diiridium(I) dichloride; (8a,9R,8′′′a,9′′′R)-9,9′-[(2,5-diphenylpyrimidine-4,6-diyl)bis(oxy)]bis(6′-methoxy-10,11-dihydrocinchonan); methanesulfonamide; nitrogen; tetrabutyl ammonium fluoride; palladium diacetate; sodium cyanoborohydride; sodium hydrogencarbonate; potassium carbonate; caesium carbonate; Dess-Martin periodane; silver nitrate; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; 9-bora-bicyclo[3.3.1]nonane; triphenylphosphine; methylamine; (3,5-dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-(1-phenyl-ethyl)-amine; potassium hexacyanoferrate(III); In tetrahydrofuran; 1,4-dioxane; dichloromethane; chloroform; water; ethyl acetate; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1002/chem.201003489
upstream raw materials:

(3S,4S)-4-N-phthalimido-1,5-hexadiene-3-ol

3-benzyloxy-4-iodo-5-nitrobenzaldehyde

methyl 3-amino-5-benzyloxy-4-iodobenzoate

C20H27NO3Si

Downstream raw materials:

C26H28N2O6

C27H29N3O7

methyl (1aS,8R,9S,9aS)-1,1a,2,8,9,9a-hexahydro-7-(benzyloxy)-8-{[(benzyloxycarbonyl)oxy]methyl}-1-(tert-butyloxycarbonyl)-8-formyl-9-hydroxy-3,9-epoxy-3H-azirino[2,3-c][1]benzazocin-5-carboxylate

methyl (1aS,8R,8aS,8bS)-1,1a,2,8,8a,8b-hexahydro-7-(benzyloxy)-8-{[(benzyloxycarbonyl)oxy]methyl}-1-(tert-butyloxycarbonyl)-8-formylazirino[2',3':3,4]pyrrolo[1,2-a]indole-5-carboxylate 3-oxide

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