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

Base Information

Chemical Name: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
CAS No.:157478-18-7
Molecular Formula:C₃₃H₃₃N₃O₉
Molecular Weight:615.64
Hs Code.:

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

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 13 articles about 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 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:

: 132628-67-2,132628-68-3
methyl (2S*,8S*)-4-benzyloxy-6-t-butoxycarbonyl-8-(t-butyldimethylsilyloxy)methyl-3-formyl-1,2,3,6,7,8-hexahydro-2-methyl-1-oxobenzo<1,2-b;4,3-b'>dipyrrole-2-carboxylate

: 157478-18-7
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:: Multi-step reaction with 5 steps

1: 99 percent / 10percent citric acid / acetic acid / 10 h / Ambient temperature

2: 48 percent / 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride, 4-dimethylaminopyridine / CH₂Cl₂ / 4 h / Ambient temperature

3: 100 percent / K₂CO₃ / methanol / 1 h / Ambient temperature

4: 10percent HCl / methanol / Ambient temperature

5: 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, NaHCO₃ / dimethylformamide / Ambient temperature

With hydrogenchloride; dmap; sodium hydrogencarbonate; potassium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; citric acid; In methanol; dichloromethane; acetic acid; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)86994-5

Reference yield:

: 143874-46-8
4-benzyloxy-6-t-butoxycarbonyl-8-hydroxymethyl-1,2,3,6,7,8-hexahydro-1,2-dioxobenzo<1,2-b;4,3-b'>dipyrrole

: 157478-18-7
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:: Multi-step reaction with 10 steps

1: 38 percent / dicyclohexylcarbodiimide, 4-dimethylaminopyridine / tetrahydrofuran / 30 min, 0 deg C; 2 h, room temp.

2: m-CPBA, NaHCO₃ / CH₂Cl₂ / 5 h / -10 - 10 °C

3: K₂CO₃ / 1.5 h / Ambient temperature

4: imidazole / 12 h / Ambient temperature

5: 88 percent / 1,8-bis(dimethylamino)naphthalene / N,N-dimethyl-acetamide / 35 h / 70 °C

6: 93 percent / Ac₂O / 9 h / Ambient temperature

7: 28 percent / LDA / tetrahydrofuran / 5.5 h / -78 °C

8: 91 percent / 10percent citric acid / acetic acid / Ambient temperature

9: 10percent HCl / methanol / Ambient temperature

10: 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, NaHCO₃ / dimethylformamide / Ambient temperature

With 1H-imidazole; hydrogenchloride; dmap; acetic anhydride; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; sodium hydrogencarbonate; potassium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; citric acid; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl acetamide; acetic acid; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)86994-5

Reference yield:

: 157393-03-8
methyl (S)-5-amino-6-benzyloxy-1-t-butoxycarbonyl-2,3-dihydro-3-hydroxymethyl-1H-indole-4-carboxylate

: 157478-18-7
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:: Multi-step reaction with 7 steps

1: imidazole / 12 h / Ambient temperature

2: 88 percent / 1,8-bis(dimethylamino)naphthalene / N,N-dimethyl-acetamide / 35 h / 70 °C

3: 93 percent / Ac₂O / 9 h / Ambient temperature

4: 28 percent / LDA / tetrahydrofuran / 5.5 h / -78 °C

5: 91 percent / 10percent citric acid / acetic acid / Ambient temperature

6: 10percent HCl / methanol / Ambient temperature

7: 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, NaHCO₃ / dimethylformamide / Ambient temperature

With 1H-imidazole; hydrogenchloride; acetic anhydride; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; sodium hydrogencarbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; citric acid; lithium diisopropyl amide; In tetrahydrofuran; methanol; N,N-dimethyl acetamide; acetic acid; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)86994-5