methyl (2R,8S)-4-benzyloxy-1,2,3,6,7,8-hexahydro-8-hydroxymethyl-2-methyl-1-oxo-6-<(5,6,7-trimethoxy-1H-indole-2-yl)carbonyl>benzo<1,2-b;4,3-b'>dipyrrole-2-carboxylate

Base Information

Chemical Name:methyl (2R*,8S*)-4-benzyloxy-1,2,3,6,7,8-hexahydro-8-hydroxymethyl-2-methyl-1-oxo-6-<(5,6,7-trimethoxy-1H-indole-2-yl)carbonyl>benzo<1,2-b;4,3-b'>dipyrrole-2-carboxylate
CAS No.:132628-70-7
Molecular Formula:C₃₃H₃₃N₃O₉
Molecular Weight:615.64
Hs Code.:

methyl (2R*,8S*)-4-benzyloxy-1,2,3,6,7,8-hexahydro-8-hydroxymethyl-2-methyl-1-oxo-6-<(5,6,7-trimethoxy-1H-indole-2-yl)carbonyl>benzo<1,2-b;4,3-b'>dipyrrole-2-carboxylate

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Chemical Property of methyl (2R*,8S*)-4-benzyloxy-1,2,3,6,7,8-hexahydro-8-hydroxymethyl-2-methyl-1-oxo-6-<(5,6,7-trimethoxy-1H-indole-2-yl)carbonyl>benzo<1,2-b;4,3-b'>dipyrrole-2-carboxylate

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Technology Process of methyl (2R*,8S*)-4-benzyloxy-1,2,3,6,7,8-hexahydro-8-hydroxymethyl-2-methyl-1-oxo-6-<(5,6,7-trimethoxy-1H-indole-2-yl)carbonyl>benzo<1,2-b;4,3-b'>dipyrrole-2-carboxylate

There total 44 articles about methyl (2R*,8S*)-4-benzyloxy-1,2,3,6,7,8-hexahydro-8-hydroxymethyl-2-methyl-1-oxo-6-<(5,6,7-trimethoxy-1H-indole-2-yl)carbonyl>benzo<1,2-b;4,3-b'>dipyrrole-2-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: 62.0%

: 128781-07-7
5,6,7-trimethoxy-1H-indole-2-carboxylic acid

: 132628-69-4,143314-85-6
methyl (2S*,8S*)-4-benzyloxy-1,2,3,6,7,8-hexahydro-8-hydroxymethyl-2-methyl-1-oxobenzo<1,2-b;4,3-b'>dipyrrole-2-carboxylate dihydrochloride

: 132628-70-7,143314-86-7,149405-53-8,149405-54-9
methyl (2S*,8S*)-4-benzyloxy-1,2,3,6,7,8-hexahydro-8-hydroxymethyl-2-methyl-1-oxo-6-<(5,6,7-trimethoxy-1H-indole-2-yl)carbonyl>benzo<1,2-b;4,3-b'>dipyrrole-2-carboxylate

Guidance literature:: With sodium hydrogencarbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; for 20h; Ambient temperature;
DOI:10.1016/S0040-4020(01)86993-3

Reference yield: 57.0%

: 128781-07-7
5,6,7-trimethoxy-1H-indole-2-carboxylic acid

: 132628-69-4,143314-85-6
methyl (2R*,8S*)-4-benzyloxy-1,2,3,6,7,8-hexahydro-8-hydroxymethyl-2-methyl-1-oxobenzo<1,2-b;4,3-b'>dipyrrole-2-carboxylate dihydrochloride

: 132628-70-7,143314-86-7,149405-53-8,149405-54-9
methyl (2R*,8S*)-4-benzyloxy-1,2,3,6,7,8-hexahydro-8-hydroxymethyl-2-methyl-1-oxo-6-<(5,6,7-trimethoxy-1H-indole-2-yl)carbonyl>benzo<1,2-b;4,3-b'>dipyrrole-2-carboxylate

Guidance literature:: With sodium hydrogencarbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; for 20h; Ambient temperature;
DOI:10.1016/S0040-4039(00)97151-X

Reference yield:

: 106014-83-9
2-[4-(benzyloxy)-2-nitrophenyl]propane-1,3-diol

: 132628-70-7,143314-86-7,149405-53-8,149405-54-9
methyl (2R*,8S*)-4-benzyloxy-1,2,3,6,7,8-hexahydro-8-hydroxymethyl-2-methyl-1-oxo-6-<(5,6,7-trimethoxy-1H-indole-2-yl)carbonyl>benzo<1,2-b;4,3-b'>dipyrrole-2-carboxylate

Guidance literature:: Multi-step reaction with 17 steps

1: 74 percent / Et₃N / CH₂Cl₂ / 2.5 h / 0 °C

2: 100 percent / Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

3: H₂, Et₃N / PtO₂ / tetrahydrofuran / 0.33 h / 2280 Torr / Ambient temperature

4: CH₂Cl₂ / 12 h / Ambient temperature

5: 77 percent / HNO₃, Ac₂O / nitromethane / 3 h / -20 °C

6: 95 percent / H₂ / PtO₂ / tetrahydrofuran / 0.25 h / 2280 Torr / Ambient temperature

7: 1.) SO₂Cl₂; 1,8-bis(dimethylamino)naphthalene, 2.) Et₃N, 3.) AcOH / 1.) CH₂Cl₂, -78 deg C, 20 min; -78 deg C, 3.5 h, 2.) CH₂Cl₂, -78 deg C, 2 h; room temp., 21 h, 3.) CH₂Cl₂, room temp., 1 h

8: CuCl₂, CuO / acetone / 1.5 h / 0 °C

9: K₂CO₃ / methanol / 2.5 h / Ambient temperature

10: imidazole / dimethylformamide / 8 h / Ambient temperature

11: m-CPBA, NaHCO₃ / CH₂Cl₂ / 2 h / -15 °C

12: K₂CO₃ / 1 h / 0 °C

13: 88 percent / 1,8-bis(dimethylamino)naphthalene / N,N-dimethyl-acetamide / 48 h / 70 °C

14: 93 percent / Ac₂O / 9 h / Ambient temperature

15: 28 percent / LDA / tetrahydrofuran / 5.5 h / -78 °C

16: 100 percent / 10percent HCl / methanol / 11 h / Ambient temperature

17: 57 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, NaHCO₃ / dimethylformamide / 20 h / Ambient temperature

With 1H-imidazole; hydrogenchloride; sulfuryl dichloride; hydrogen; nitric acid; acetic anhydride; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; sodium hydrogencarbonate; potassium carbonate; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; copper(II) oxide; copper dichloride; lithium diisopropyl amide; platinum(IV) oxide; In tetrahydrofuran; methanol; nitromethane; dichloromethane; N,N-dimethyl acetamide; N,N-dimethyl-formamide; acetone;
DOI:10.1016/S0040-4020(01)86993-3