CAS No.103060-53-3,Daptomycin Suppliers,MSDS download

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Basic Information

Molecular Structure:
CAS No.:	103060-53-3
Name:	Daptomycin

Formula:	C₇₂H₁₀₁ N₁₇ O₂₆
Molecular Weight:	1620.69
Synonyms:	Benzenebutanoic acid, N-(1-oxodecyl)-L-tryptophyl-D-asparaginyl-L-a-aspartyl-L-threonylglycyl-L-ornithyl-L-a-aspartyl-D-alanyl-L-a-aspartylglycyl-D-seryl-(3R)-3-methyl-L-a-glutamyl-a,2-diamino-g-oxo-, (13?;4)-lactone, (aS)-;Cidecin;Cubicin;Dapcin;Daptomicina;Daptomycine;Daptomycinum;Deptomycin;LY 146032;N-(1-Oxodecyl)-L-tryptophyl-D-asparaginyl-L-a-aspartyl-L-threonylglycyl-L-ornithyl-L-a-aspartyl-D-alanyl-L-a-aspartylglycyl-D-seryl-(3R)-3-methyl-L-a-glutamyl-(aS)-a,2-diamino-g-oxobenzenebutanoicacid (13?;
EINECS:	600-389-2
Density:	1.45 g/cm³
Melting Point:	202-204?C
Boiling Point:	2078.2 °C at 760 mmHg
Flash Point:	1210.7 °C
Appearance:	White powder
PSA:	702.02000
LogP:	0.88280

Synthetic route

: 334-48-5
1-decanoic acid

: 29022-11-5
N-(fluoren-9-ylmethoxycarbonyl)glycine

: 1429504-34-6
(2S,3R)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-(tert-butoxy)-3-methyl-5-oxopentanoic acid

: C23H20N4O3

: C62H58N4O15

: 35661-38-2, 35661-39-3, 79990-15-1
N-(9-fluorenylmethoxycarbonyl)-D-alanine

: 73731-37-0
Fmoc-Thr-OH

: 73724-45-5, 136083-72-2, 116861-26-8
(R)-N-(fluoren-9-ylmethoxycarbonyl)serine

: 109425-55-0
Fmoc-Orn(Boc)-OH

: 88223-98-7
p-toluenesulfonic acid salt of glycine allyl ester

: 144120-53-6
(S)-3-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-(allyloxy)-4-oxobutanoic acid

: 144120-52-5
4-(1,1-dimethylethyl) ester of Nα-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-aspartic acid allyl ester

: 333366-23-7
(S)-(−)-4-tert-butyl 2-azidosuccinic acid

: (S)-2-azido-3-(1-(tert-butoxycarbonyl)-1H-indol-3-yl)propanoic acid

: 103060-53-3
daptomycin

Conditions

Conditions	Yield
Stage #1: (S)-3-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-(allyloxy)-4-oxobutanoic acid With N-ethyl-N,N-diisopropylamine In dichloromethane for 4h; 2-chlorotrityl chloride resin; Stage #2: With tetrakis(triphenylphosphine) palladium(0); 1,3-dimethylbarbituric acid In dichloromethane; N,N-dimethyl-formamide for 1h; 2-chlorotrityl chloride resin; Stage #3: 1-decanoic acid; N-(fluoren-9-ylmethoxycarbonyl)glycine; (2S,3R)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-(tert-butoxy)-3-methyl-5-oxopentanoic acid; C23H20N4O3; C62H58N4O15; N-(9-fluorenylmethoxycarbonyl)-D-alanine; Fmoc-Thr-OH; (R)-N-(fluoren-9-ylmethoxycarbonyl)serine; Fmoc-Orn(Boc)-OH; p-toluenesulfonic acid salt of glycine allyl ester; 4-(1,1-dimethylethyl) ester of Nα-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-aspartic acid allyl ester; (S)-(−)-4-tert-butyl 2-azidosuccinic acid; (S)-2-azido-3-(1-(tert-butoxycarbonyl)-1H-indol-3-yl)propanoic acid Further stages;	9%

Yield

Stage #1: (S)-3-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-(allyloxy)-4-oxobutanoic acid With N-ethyl-N,N-diisopropylamine In dichloromethane for 4h; 2-chlorotrityl chloride resin;
Stage #2: With tetrakis(triphenylphosphine) palladium(0); 1,3-dimethylbarbituric acid In dichloromethane; N,N-dimethyl-formamide for 1h; 2-chlorotrityl chloride resin;
Stage #3: 1-decanoic acid; N-(fluoren-9-ylmethoxycarbonyl)glycine; (2S,3R)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-(tert-butoxy)-3-methyl-5-oxopentanoic acid; C23H20N4O3; C62H58N4O15; N-(9-fluorenylmethoxycarbonyl)-D-alanine; Fmoc-Thr-OH; (R)-N-(fluoren-9-ylmethoxycarbonyl)serine; Fmoc-Orn(Boc)-OH; p-toluenesulfonic acid salt of glycine allyl ester; 4-(1,1-dimethylethyl) ester of Nα-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-aspartic acid allyl ester; (S)-(−)-4-tert-butyl 2-azidosuccinic acid; (S)-2-azido-3-(1-(tert-butoxycarbonyl)-1H-indol-3-yl)propanoic acid Further stages;

...Expand

dimethylallyl pyrophosphate: dimethylallyl pyrophosphate

: C77H109N17O26

Conditions

Conditions	Yield
In aq. buffer at 37℃; for 12h; pH=8;	60%

: 103060-53-3
daptomycin

: C82H102N6O16

: C153H199N23O42

Conditions

Conditions	Yield
Stage #1: C82H102N6O16 With 4-methyl-morpholine; isobutyl chloroformate In tetrahydrofuran at 0℃; for 1h; Stage #2: daptomycin With sodium hydrogencarbonate In tetrahydrofuran; water at 0 - 20℃;	48%

: 159857-81-5
N-[6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoyl]-L-valyl-N5-carbamoyl-N[4-({[(4-nitrophenoxy)carbonyl]oxy}methyl)phenyl]-L-ornithinamide

: 103060-53-3
daptomycin

: MC-vc-PAB-daptomycin

Conditions

Conditions	Yield
With benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; Sealed tube;	44%

: 103060-53-3
daptomycin

: C24H25N3O9

: C92H121N19O33

Conditions

Conditions	Yield
With sodium hydrogencarbonate In tetrahydrofuran; water at 20℃; for 20h;	37%

: 103060-53-3
daptomycin

: 22679-02-3
dimethylallyl pyrophosphate

C77H109N17O26: C77H109N17O26

Conditions

Conditions	Yield
In aq. buffer at 37℃; for 12h; pH=8;	6%

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History

Daptomycin (CAS NO.103060-53-3) was originally discovered by researchers at Eli Lilly and Company in the 1980s, who designated the compound LY 146032. It showed promise in Phase I/II clinical trials for the treatment of infections caused by Gram-positive organisms. However, high dose therapy was found to be associated with adverse effects on skeletal muscle, including myalgia and the potential for myositis, and Lilly ceased development. The rights to LY 146032 were subsequently acquired by Cubist Pharmaceuticals in 1997. Food and Drug Administration (FDA) approval in September 2003. Daptomycin is marketed in the EU and several other countries by Novartis following its buying of Chiron Corporation. Outside of the US, Daptomycin is available in Canada and many European countries, with further launches expected in 2008.

Specification

1. Introduction of Daptomycin

Daptomycin is one kind of white crystalline powder, odorless, little bitter taste. If you want to keep it, it should be stored in cool and dry places, keep away from light. Besids, this chemical belongs to the Product Category which include Antibacterial; Intermediates & Fine Chemicals; Pharmaceuticals. In addition, Daptomycin is a naturally-occurring compound found in the soil saprotroph Streptomyces roseosporus.

2. Properties of Daptomycin

Daptomycin has the following property datas: (1)Density: 1.45 g/cm³; (2)Index of Refraction: 1.638; (3)Flash Point: 1210.7 °C; (4)Enthalpy of Vaporization: 366.93 kJ/mol; (5)Boiling Point: 2078.2 °C at 760 mmHg.

3. Structure Descriptors of Daptomycin

You could convert the following datas into the molecular structure:
(1). InChI: InChI=1S/C72H101N17O26/c1-5-6-7-8-9-10-11-22-53(93)81-44(25-38-31-76-42-20-15-13-17-39(38)42)66(108)84-45(27-52(75)92)67(109)86-48(30-59(102)103)68(110)89-61-37(4)115-72(114)49(26-51(91)40-18-12-14-19-41(40)74)87-71(113)60(35(2)24-56(96)97)88-69(111)50(34-90)82-55(95)32-77-63(105)46(28-57(98)99)83-62(104)36(3)79-65(107)47(29-58(100)101)85-64(106)43(21-16-23-73)80-54(94)33-78-70(61)112/h12-15,17-20,31,35-37,43-50,60-61,76,90H,5-11,16,21-30,32-34,73-74H2,1-4H3,(H2,75,92)(H,77,105)(H,78,112)(H,79,107)(H,80,94)(H,81,93)(H,82,95)(H,83,104)(H,84,108)(H,85,106)(H,86,109)(H,87,113)(H,88,111)(H,89,110)(H,96,97)(H,98,99)(H,100,101)(H,102,103)/t35?,36-,37?,43+,44+,45+,46+,47+,48+,49+,50-,60+,61?/m1/s1
(2). InChIKey: InChIKey=DOAKLVKFURWEDJ-OFNKPWESSA-N
(3). Smiles: C(=O)(N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)NC1C(=O)NCC(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@@H](CC(=O)O)C(=O)NCC(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)OC1C)CC(=O)c1ccccc1N)[C@@H](CC(=O)O)C)CO)C)CC(=O)O)CCCN)CC(=O)O)CC(=O)N)Cc1c[nH]c2c1cccc2)CCCCCCCCC

4. Use of Daptomycin

Daptomycin is a novel lipopeptide antibiotic used in the treatment of certain infections caused by Gram-positive organisms. Its distinct mechanism of action means that it may be useful in treating infections caused by multi-resistant bacteria.