5-((R)-1,5-Dimethyl-1-vinyl-hex-4-enyl)-13-hydroxymethyl-10-isopropyl-9-methyl-3,9,12-triaza-tricyclo[6.6.1.0^4,15]pentadeca-1,4⁽¹⁵⁾,5,7-tetraen-11-one

Base Information

• Chemical Name: 5-((R)-1,5-Dimethyl-1-vinyl-hex-4-enyl)-13-hydroxymethyl-10-isopropyl-9-methyl-3,9,12-triaza-tricyclo[6.6.1.0^4,15]pentadeca-1,4⁽¹⁵⁾,5,7-tetraen-11-one
• CAS No.: 112653-02-8
• Molecular Formula: C₂₇H₃₉N₃O₂
• Molecular Weight: 437.626

Synonyms:

Chemical Property of 5-((R)-1,5-Dimethyl-1-vinyl-hex-4-enyl)-13-hydroxymethyl-10-isopropyl-9-methyl-3,9,12-triaza-tricyclo[6.6.1.0^4,15]pentadeca-1,4⁽¹⁵⁾,5,7-tetraen-11-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of 5-((R)-1,5-Dimethyl-1-vinyl-hex-4-enyl)-13-hydroxymethyl-10-isopropyl-9-methyl-3,9,12-triaza-tricyclo[6.6.1.0^4,15]pentadeca-1,4⁽¹⁵⁾,5,7-tetraen-11-one

There total 22 articles about 5-((R)-1,5-Dimethyl-1-vinyl-hex-4-enyl)-13-hydroxymethyl-10-isopropyl-9-methyl-3,9,12-triaza-tricyclo[6.6.1.0^4,15]pentadeca-1,4⁽¹⁵⁾,5,7-tetraen-11-one 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: 63.0%

C33H53N3O2Si (1638769-41-1) → Lyngbyatoxin A (70497-14-2,102209-77-8,112652-99-0,112653-00-6,112653-01-7,112653-02-8,138512-80-8,138512-81-9,56645-57-9)

Guidance literature:

With lithium tetrafluoroborate; camphor-10-sulfonic acid; In tetrahydrofuran; at 23 ℃;

DOI:10.1039/c4sc00256c

Reference yield: 4.0%

(S)-2-{[3-(2-Amino-3-hydroxy-propyl)-7-((R)-1,5-dimethyl-1-vinyl-hex-4-enyl)-1H-indol-4-yl]-methyl-amino}-3-methyl-butyric acid → (+)-Teleocicin A-2 (70497-14-2,102209-77-8,112652-99-0,112653-00-6,112653-01-7,112653-02-8,138512-80-8,138512-81-9,56645-57-9) + (10S,13R)-5-((R)-1,5-Dimethyl-1-vinyl-hex-4-enyl)-13-hydroxymethyl-10-isopropyl-9-methyl-3,9,12-triaza-tricyclo[6.6.1.04,15]pentadeca-1,4,6,8(15)-tetraen-11-one (70497-14-2,102209-77-8,112652-99-0,112653-00-6,112653-01-7,112653-02-8,138512-80-8,138512-81-9,56645-57-9) + Lyngbyatoxin A (70497-14-2,102209-77-8,112652-99-0,112653-00-6,112653-01-7,112653-02-8,138512-80-8,138512-81-9,56645-57-9)

Guidance literature:

With diphenylphosphoranyl azide; triethylamine; In N,N-dimethyl-formamide; 0 deg C, 1 h, then room temp. 24 h;

DOI:10.1016/S0040-4039(00)96097-0

Reference yield: 4.0%

(S)-2-{[3-(2-Amino-3-hydroxy-propyl)-7-((R)-1,5-dimethyl-1-vinyl-hex-4-enyl)-1H-indol-4-yl]-methyl-amino}-3-methyl-butyric acid → (+)-Teleocicin A-2 (70497-14-2,102209-77-8,112652-99-0,112653-00-6,112653-01-7,112653-02-8,138512-80-8,138512-81-9,56645-57-9) + (10S,13R)-5-((R)-1,5-Dimethyl-1-vinyl-hex-4-enyl)-13-hydroxymethyl-10-isopropyl-9-methyl-3,9,12-triaza-tricyclo[6.6.1.04,15]pentadeca-1,4,6,8(15)-tetraen-11-one (70497-14-2,102209-77-8,112652-99-0,112653-00-6,112653-01-7,112653-02-8,138512-80-8,138512-81-9,56645-57-9) + Lyngbyatoxin A (70497-14-2,102209-77-8,112652-99-0,112653-00-6,112653-01-7,112653-02-8,138512-80-8,138512-81-9,56645-57-9)

Guidance literature:

With diphenylphosphoranyl azide; triethylamine; In N,N-dimethyl-formamide; 0 deg C, 1 h, then room temp. 24 h;

DOI:10.1016/S0040-4039(00)96097-0

upstream raw materials:

N-methyl-L-valyl-L-tryptophanol

(-)-7-bromo-14-O-TBDMS-indolactam-V

C₃₆H₅₈N₄O₄Si

C₃₂H₅₁N₃O₃Si

Downstream raw materials:

21,22-dihydroteleocidin A-2

21,22-dihydroteleocidin A-1

teleocidin B-4

des-O-methyl-olivoretin C

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