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

Base Information

Chemical Name: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
CAS No.:157478-34-7
Molecular Formula:C₃₃H₄₄N₂O₈Si
Molecular Weight:624.806
Hs Code.:

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

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 8 articles about 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 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: 28.0%

: methyl (S)-6-benzyloxy-1-t-butoxycarbonyl-3-(t-butyldimethylsilyloxy)methyl-2,3-dihydro-5-<(RS)-N-formyl-N-(1-methoxycarbonylethyl)>amino-1H-indole-4-carboxylate

: 157478-34-7
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

: 157478-33-6
methyl (2R,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

Guidance literature:: With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 5.5h;
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

: 157478-34-7
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

Guidance literature:: Multi-step reaction with 7 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

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

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 157478-34-7
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

Guidance literature:: Multi-step reaction with 4 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

With 1H-imidazole; acetic anhydride; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; lithium diisopropyl amide; In tetrahydrofuran; N,N-dimethyl acetamide;
DOI:10.1016/S0040-4020(01)86994-5