688316-86-1|Allyl (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-aminobutanoate| Ambeed

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Quality Control of [ 688316-86-1 ] Purity: 95% SDS Specification

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NMR

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Product Details of [ 688316-86-1 ]

CAS No. :	688316-86-1
Formula :	C₂₂H₂₄N₂O₄
M.W :	380.44
SMILES Code :	C=CCOC([C@H](CCN)NC(OCC1C2=CC=CC=C2C3=CC=CC=C31)=O)=O
MDL No. :	N/A

Safety of [ 688316-86-1 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319
Precautionary Statements:	P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P337+P313-P363-P405-P501

Application In Synthesis of [ 688316-86-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 688316-86-1 ]

[ 688316-86-1 ] Synthesis Path-Downstream 1~29

1
[ 125238-99-5 ]
[ 688316-86-1 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 2199 - 2203.

2
(2S)-4-[[1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethyl]amino]-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]butanoic acid [ No CAS ]
[ 929-10-2 ]
[ 35661-60-0 ]
[ 71989-35-0 ]
[ 86123-10-6 ]
[ 125238-99-5 ]
[ 688316-86-1 ]
6-methylheptanoyl-X-T-X-cyclo[X-X-DF-L-X-X-T] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
25%		General procedure: 2CTC resin (0.47g,loading = 0.53mmol/g ) was swelled in DCM/DMF for 20min before use. Then,Fmoc-Dab-OAll (1mmol, 4 eq), 8 eq. DIEA and 4ml DMF were added to react withresin for 12hr. The resin was capped with 200 mlmethanol to quench the remaining 2-chlorotrityl chloride. Generally, thesubsequent coupling was carried out using a solution of 4 eq. Fmoc-amino acid,3.8 eq. HCTU, and 8 eq. DIEA in DMF at 30 oC. Each coupling steprequired 1hr and the resin was washed by DMF and DCM before Fmoc-deprotection. The Fmoc group wasremoved by treatment with 20% piperidine in DMF twice (5 min, 10 min) followedby DMF and DCM wash. Dde group wasremoved by treatment with 3% NH2NH2/DMF for 20min threetimes. Allyl group wasremoved by treatment with PhSiH3 (10 eq.), Pd(PPh3)4(2 eq.) in 50% DCM/50% DMF for 3 hrs. After deprotection, the resin waswashed with DCM, 0.5% sodium diethyldithiocarbamate in DMF and DMF severaltimes. The finalcyclization step was carried out with 4 eq. PyAOP, 4eq. HOAt and 8eq.NMM for12hr. The cleavage reagentwas chose as TFA/water/TIPS (95/2.5/2.5). It was added into the dry resinprewashed with DCM and the cleavage was carried out for 1.5 hr. The TFAsolution was concentrated by blowing with N2. The crude peptideswere obtained by precipitating with cold diethyl ether, purified bysemi-preparative HPLC and lyophilized to achieve pure product.

References: [1]Tetrahedron Letters,2015,vol. 56,p. 4796 - 4799.

3
(2S)-4-[[1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethyl]amino]-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]butanoic acid [ No CAS ]
[ 35661-60-0 ]
[ 71989-35-0 ]
[ 86123-10-6 ]
[ 125238-99-5 ]
[ 181954-34-7 ]
[ 688316-86-1 ]
[ 92-92-2 ]
C₅₉H₈₈N₁₆O₁₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
28%		General procedure: 2CTC resin (0.47g,loading = 0.53mmol/g ) was swelled in DCM/DMF for 20min before use. Then,Fmoc-Dab-OAll (1mmol, 4 eq), 8 eq. DIEA and 4ml DMF were added to react withresin for 12hr. The resin was capped with 200 mlmethanol to quench the remaining 2-chlorotrityl chloride. Generally, thesubsequent coupling was carried out using a solution of 4 eq. Fmoc-amino acid,3.8 eq. HCTU, and 8 eq. DIEA in DMF at 30 oC. Each coupling steprequired 1hr and the resin was washed by DMF and DCM before Fmoc-deprotection. The Fmoc group wasremoved by treatment with 20% piperidine in DMF twice (5 min, 10 min) followedby DMF and DCM wash. Dde group wasremoved by treatment with 3% NH2NH2/DMF for 20min threetimes. Allyl group wasremoved by treatment with PhSiH3 (10 eq.), Pd(PPh3)4(2 eq.) in 50% DCM/50% DMF for 3 hrs. After deprotection, the resin waswashed with DCM, 0.5% sodium diethyldithiocarbamate in DMF and DMF severaltimes. The finalcyclization step was carried out with 4 eq. PyAOP, 4eq. HOAt and 8eq.NMM for12hr. The cleavage reagentwas chose as TFA/water/TIPS (95/2.5/2.5). It was added into the dry resinprewashed with DCM and the cleavage was carried out for 1.5 hr. The TFAsolution was concentrated by blowing with N2. The crude peptideswere obtained by precipitating with cold diethyl ether, purified bysemi-preparative HPLC and lyophilized to achieve pure product.

References: [1]Tetrahedron Letters,2015,vol. 56,p. 4796 - 4799.

4
(2S)-4-[[1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethyl]amino]-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]butanoic acid [ No CAS ]
[ 929-10-2 ]
[ 35661-60-0 ]
[ 71989-35-0 ]
[ 35661-60-0 ]
[ 125238-99-5 ]
[ 688316-86-1 ]
polymyxin E₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
25%		General procedure: 2CTC resin (0.47g,loading = 0.53mmol/g ) was swelled in DCM/DMF for 20min before use. Then,Fmoc-Dab-OAll (1mmol, 4 eq), 8 eq. DIEA and 4ml DMF were added to react withresin for 12hr. The resin was capped with 200 mlmethanol to quench the remaining 2-chlorotrityl chloride. Generally, thesubsequent coupling was carried out using a solution of 4 eq. Fmoc-amino acid,3.8 eq. HCTU, and 8 eq. DIEA in DMF at 30 oC. Each coupling steprequired 1hr and the resin was washed by DMF and DCM before Fmoc-deprotection. The Fmoc group wasremoved by treatment with 20% piperidine in DMF twice (5 min, 10 min) followedby DMF and DCM wash. Dde group wasremoved by treatment with 3% NH2NH2/DMF for 20min threetimes. Allyl group wasremoved by treatment with PhSiH3 (10 eq.), Pd(PPh3)4(2 eq.) in 50% DCM/50% DMF for 3 hrs. After deprotection, the resin waswashed with DCM, 0.5% sodium diethyldithiocarbamate in DMF and DMF severaltimes. The finalcyclization step was carried out with 4 eq. PyAOP, 4eq. HOAt and 8eq.NMM for12hr. The cleavage reagentwas chose as TFA/water/TIPS (95/2.5/2.5). It was added into the dry resinprewashed with DCM and the cleavage was carried out for 1.5 hr. The TFAsolution was concentrated by blowing with N2. The crude peptideswere obtained by precipitating with cold diethyl ether, purified bysemi-preparative HPLC and lyophilized to achieve pure product.

References: [1]Tetrahedron Letters,2015,vol. 56,p. 4796 - 4799.

5
[ 504-99-4 ]
Fmoc-L-Dab(Dde)-OH, DDE = 1-(4,4-dimethyl-2,6-dioxocylohexylidene)ethyl [ No CAS ]
[ 71989-35-0 ]
[ 86123-10-6 ]
[ 125238-99-5 ]
[ 76-05-1 ]
[ 688316-86-1 ]
Fmoc-D-Ser(pg)-OH [ No CAS ]
polymyxin S₁ TFA salt [ No CAS ]