84129-60-2

Basic information

• Product Name: trans-(1S,3R)-(-)-2-benzyl-3-methoxycarbonyl-1-methoxycarbonylethyl-9-methyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole
• Synonyms: trans-(1S,3R)-(-)-2-benzyl-3-methoxycarbonyl-1-methoxycarbonylethyl-9-methyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole
• CAS NO: 84129-60-2
• Molecular Weight: 420.508
• Mol File: 84129-60-2.mol
• Article Data: 11

Chemical Properties

• CAS DataBase Reference: trans-(1S,3R)-(-)-2-benzyl-3-methoxycarbonyl-1-methoxycarbonylethyl-9-methyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole(CAS DataBase Reference)
• NIST Chemistry Reference: trans-(1S,3R)-(-)-2-benzyl-3-methoxycarbonyl-1-methoxycarbonylethyl-9-methyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole(84129-60-2)
• EPA Substance Registry System: trans-(1S,3R)-(-)-2-benzyl-3-methoxycarbonyl-1-methoxycarbonylethyl-9-methyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole(84129-60-2)

Safety Data

• Hazardous Substances Data: 84129-60-2(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 60702-96-7 2-benzyl-3-(methoxycarbonyl)-9-methyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole-1-propionic acid 
• 84094-74-6 methyl trans-2-benzyl-3-methoxycarbonyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole-1-propionate 
• 74-88-4 methyl iodide 
• 84094-74-6 (1S,3R)-(-)-methyl 2-benzyl-3-methoxycarbonyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole-1-propionate 
• 13865-19-5 4-oxobutanoic acid methyl ester 
• 19779-77-2 (+/-)-N_a-methyl-N_b-benzyltriptophan methyl ester hydrochloride 
• 4220-66-0 methyl 4,4-dimethoxybutanoate 
• 120053-66-9 D-(+)-N_a-methyl-N_b-benzyltryptophan methyl ester 
• 19779-74-9 (R)-3-(1-Methyl-1H-indol-3-yl)-2-{[1-phenyl-meth-(E)-ylidene]-amino}-propionic acid methyl ester 
• 120056-44-2 cis-(1R,3R)-(+)-2-benzyl-3-methoxycarbonyl-1-methoxycarbonylethyl-9-methyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole 
• 119980-65-3 1-methyl-2-(3-methoxycarbonylpropan-1-methoxy-1-yl)-3-(R)-<1-(benzylamine)-1-(methoxycarbonylethan-2-yl)>indole 
• 119980-66-4 1-methyl-2-(E)-(3-methoxycarbonylpropyl-1-en-1-yl)-3-(R)-<1-(benzylamine)-1-(methoxycarbonylethan-2-yl)>indole 
• 186581-53-3 diazomethane 

Downstream Products

• 4837-57-4 methyl trans-2-benzyl-3-methoxycarbonyl-9-methyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole-1-propionate 
• 2738-25-2 methyl 5-methyl-9-oxo-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctaindole-8-carboxylate 
• 4837-58-5 trans-2-benzyl-3-carboxy-9-methyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole-1-propionic acid 
• 302356-98-5 (6S,10S)-(-)-5-methyl-9-oxo-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole 
• 22282-00-4 (+/)-5-Methyl-9-oxo-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole 
• 122490-92-0 5-methyl-9-hydroxy-9α-chloro-phenylsulfinylmethyl-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole 
• 122490-83-9 2'-phenylsulfinyl-5-methyl-12-benzyl-6,7,8,9,10,11-hexahydro-oxirano-spiro<2',9>-6,10-imino-5H-cyclooctindole 
• 141804-40-2 5-methyl-9-butyryloxymethyl-12-benzyl-6,7,10,11-tetrahydro-6,10-imino-5H-cyclooctindole 
• 122490-84-0 5-methyl-9-formyl-12-benzyl-6,7,10,11-tetrahydro-6,10-imino-5H-cyclooctindole 
• 122490-85-1 5-methyl-9-hydroxymethyl-12-benzyl-6,7,10,11-tetrahydro-6,10-imino-5H-cyclooctindole 
• 210552-30-0 C₃₀H₃₆N₂O 
• 210552-31-1 C₃₂H₄₀N₂O₂ 
• 143065-07-0 (-)-(6S,8S,9S,10S,1'R)-5-methyl-8-(1'-ethyl-2'-oxoethyl)-9-(1',3'-dioxolan-2'-yl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooct[b]indole 
• 143065-03-6 (6S,8S,9S,10S,1'S)-5-methyl-8-(1'-ethyl-oxomethyl)-9-(1',3'-dioxolan-2'-yl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooct[b]-indole 

Relevant articles and documents

Enantiospecific Total Synthesis of the Sarpagine Related Indole Alkaloids Talpinine and Talcarpine as Well as the Improved Total Synthesis of Alstonerine and Anhydromacrosalhine-methine via the Asymmetric Pictet-Spengler Reaction

The enantiospecific total synthesis of talpinine 1 and talcarpine 2 has been accomplished from D-(+)-tryptophan in 13 steps (11 reaction vessels) in 10% and 9.5% overall yields, respectively. Moreover, this synthetic approach has been employed for the improved synthesis of alstonerine 3 and anhydromacrosalhine-methine 4 in 12% and 14% overall yield, respectively. A convenient synthetic route for the enantiospecific, stereospecific preparation of the key intermediate (-)-Na-H, Nb-benzyl tetracyclic ketone 15a via the asymmetric Pictet-Spengler reaction on a multihundredgram scale has been developed. A diastereocontrolled (>30:1) anionic oxy-Cope rearrangement and the intramolecular rearrangement to form ring-E and an Nb-benzyl/Nb-methyl transfer reaction also served as key steps. This general approach can now be utilized for the synthesis of macroline/ sarpagine related indole alkaloids and their antipodes for biological screening.

General Approach to the Synthesis of Sarpagine and Ajmaline Alkaloids. Enantiospecific Total Synthesis of (+)-Ajmaline and Alkaloid G via the Asymmetric Pictet-Spengler Reaction

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Pictet-Spengler reactions in aprotic media. The total synthesis of (±) suaveoline

The first total synthesis of the indole alkaloid (±)-suaveoline 1 (a macroline-related base and a member of the sarpagine/ajmaline class of alkaloids) was completed in a stereocontrolled fashion. The serial synthesis employed three intramolecular reaction