Desotamide

Base Information

• Chemical Name: Desotamide
• CAS No.: 194660-14-5
• Molecular Formula: C35H52N8O7
• Molecular Weight: 696.845
• Mol file: 194660-14-5.mol

Synonyms:

Chemical Property of Desotamide

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 1171.4°C at 760 mmHg
• Flash Point: 662.2°C
• Density: 1.134g/cm³

Purity/Quality:

97% ^*data from raw suppliers

Desotamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: The cyclic hexapeptide, desotamide, was first isolated from a Streptomyces sp. found to produce salinamide A, an inhibitor of bacterial RNA polymerase. Little is known of desotamide's intrinsic activity or potency. Desotamide is a compound found to produce salinamide A showing inhibition of bacterial RNA polymerase.

Technology Process of Desotamide

There total 2 articles about Desotamide 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: 78.5%

N-(fluoren-9-ylmethoxycarbonyl)glycine (29022-11-5) + Fmoc-Leu-OH (35661-60-0) + Fmoc-Ile-OH (71989-23-6,251316-98-0) + N-(9-fluorenylmethoxycarbonyl)-D-leucine (35661-60-0,126727-03-5,114360-54-2) + (S)-3-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-(allyloxy)-4-oxobutanoic acid (144120-53-6) + 3-[(S)-2-carboxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl]indole-1-carboxylic acid tert-butyl ester (143824-78-6,163619-04-3) → cyclo[Asn-Ile-D-Leu-Leu-Trp-Gly] (194660-14-5)

Guidance literature:

(S)-3-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-(allyloxy)-4-oxobutanoic acid; With 6-chloro-3-((dimethylamino)(dimethyliminio)methyl)-1H-benzo[d][1,2,3]triazol-3-ium-1-olatehexafluorophosphate(V); N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃; for 1h;

With piperidine; In N,N-dimethyl-formamide; at 20 ℃; for 0.25h;

N-(fluoren-9-ylmethoxycarbonyl)glycine; Fmoc-Leu-OH; Fmoc-Ile-OH; N-(9-fluorenylmethoxycarbonyl)-D-leucine; 3-[(S)-2-carboxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl]indole-1-carboxylic acid tert-butyl ester; Further stages;

DOI:10.1002/cbdv.201700414

Reference yield:

C59H74N8O9 → cyclo[Asn-Ile-D-Leu-Leu-Trp-Gly] (194660-14-5)

Guidance literature:

C₅₉H₇₄N₈O₉; With chlorotriisopropylsilane; trifluoroacetic acid; In dichloromethane; for 0.5h;

In methanol; dichloromethane; Alkaline conditions;

DOI:10.1021/acscombsci.7b00189

Reference yield:

1-fluoro-2-4-dinitrophenyl-5-L-alanine amide + desotamide A (194660-14-5) → Gly-L-FDAA + L-FDAA-L-Leu (128424-93-1) + L-FDAA-D-leucine (128425-06-9) + L-FDAA-L-allo-Ile + FDAA-L-Asp (141779-59-1) + L-FDAA-L-Asp-OH

Guidance literature:

desotamide A; With hydrogenchloride; In water; at 110 ℃; for 24h;

1-fluoro-2-4-dinitrophenyl-5-L-alanine amide; With sodium hydrogencarbonate; In acetone; at 40 ℃; for 1h;

DOI:10.1021/ol502472c

upstream raw materials:

N-(fluoren-9-ylmethoxycarbonyl)glycine

Fmoc-Leu-OH

Fmoc-Ile-OH

N-(9-fluorenylmethoxycarbonyl)-D-leucine

Downstream raw materials:

L-FDAA-L-Leu

L-FDAA-D-leucine

FDAA-L-Asp