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Chemical Structure| 161420-87-7 Chemical Structure| 161420-87-7

Structure of Fmoc-Dab-OH
CAS No.: 161420-87-7

Chemical Structure| 161420-87-7

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Product Details of [ 161420-87-7 ]

CAS No. :161420-87-7
Formula : C19H20N2O4
M.W : 340.37
SMILES Code : O=C(O)[C@@H](NC(OCC1C2=C(C3=C1C=CC=C3)C=CC=C2)=O)CCN
MDL No. :MFCD00237017
InChI Key :ZZDRDGKSMGGBDI-KRWDZBQOSA-N
Pubchem ID :7019708

Safety of [ 161420-87-7 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 161420-87-7 ]

* 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 [ 161420-87-7 ]

[ 161420-87-7 ] Synthesis Path-Downstream   1~36

  • 1
  • [ 24424-99-5 ]
  • [ 161420-87-7 ]
  • [ 125238-99-5 ]
YieldReaction ConditionsOperation in experiment
86.62% With sodium hydroxide; In water; acetone; at 0 - 10℃; for 4h;pH 7.5 - 8; B. The suspension 50g146 . 8nmol<strong>[161420-87-7]Fmoc-Dab-OH</strong> with 700 ml acetone: water = 1:in 1(v/v), in 0-10 °C add 38.4g176 . 1nmol (Boc)2O, 0.5NNaOH adjusting pH= 7.5-8, reaction 4 hours after Fmoc-Dab (Boc)-OH56g processing product, yield 86.62percent, HPLC99 . 4percent. The infrared, nuclear magnetic resonance confirmed correct structure, see Figure 3, Figure 4.
  • 2
  • [ 71989-20-3 ]
  • [ 161420-87-7 ]
YieldReaction ConditionsOperation in experiment
86.5% With [bis(acetoxy)iodo]benzene; In water; ethyl acetate; acetonitrile; at 20 - 30℃; for 72h; A. The suspension 100g271 . 5nmolFmoc-Gln-OH with 2L ethyl acetate: acetonitrile: water = 2:1: mixed solution 1(v/v/v), in 20-30 C add 105.1g325 . 9nmolDipa, reaction 72 hours, post-processed to obtain product Fmoc-Dab-OH80g. Yield of 86.5%, HPLC: 99.6%. The infrared, nuclear magnetic resonance confirmed correct structure, see Figure 1, Figure 2.
  • 3
  • [ 29022-11-5 ]
  • [ 73724-45-5 ]
  • [ 116611-64-4 ]
  • [ 161420-87-7 ]
  • 5-(dimethylamino)naphthalene-1-sulfonamide [ No CAS ]
  • (S)-2-Amino-N-[(S)-1-[(S)-1-((S)-1-carbamoyl-2-hydroxy-ethylcarbamoyl)-2-hydroxy-ethylcarbamoyl]-2-(1H-imidazol-4-yl)-ethylcarbamoyl]-methyl}-4-(5-dimethylamino-naphthalene-1-sulfonylamino)-butyramide [ No CAS ]
  • 4
  • [ 1694-92-4 ]
  • [ 161420-87-7 ]
  • Nα-(9-fluorenylmethoxycarbonyl)-Nβ-2-nitrobenzenesulfonyl-L-2,4-diaminobutyric acid [ No CAS ]
  • 5
  • [ 863646-23-5 ]
  • [ 161420-87-7 ]
  • [ 863922-39-8 ]
  • 6
  • [ 65853-65-8 ]
  • [ 161420-87-7 ]
  • [ 811434-05-6 ]
  • 7
  • [ 911132-23-5 ]
  • [ 161420-87-7 ]
  • 4-{2-[2-(bis-<i>tert</i>-butoxycarbonylmethyl-amino)-ethoxy]-acetylamino}-2-(9<i>H</i>-fluoren-9-ylmethoxycarbonylamino)-butyric acid [ No CAS ]
  • 8
  • [ 911132-25-7 ]
  • [ 161420-87-7 ]
  • 4-(2-[2-(bis-<i>tert</i>-butoxycarbonylmethyl-amino)-ethyl]-<i>tert</i>-butoxycarbonyl-amino}-acetylamino)-2-(9<i>H</i>-fluoren-9-ylmethoxycarbonylamino)-butyric acid [ No CAS ]
  • 9
  • [ 193143-26-9 ]
  • [ 161420-87-7 ]
  • 4-(2-[2-(bis-<i>tert</i>-butoxycarbonylmethyl-amino)-ethyl]-<i>tert</i>-butoxycarbonylmethyl-amino}-acetylamino)-2-(9<i>H</i>-fluoren-9-ylmethoxycarbonylamino)-butyric acid [ No CAS ]
  • 10
  • C20H38N7O5Pol [ No CAS ]
  • [ 161420-87-7 ]
  • C39H56N9O8Pol [ No CAS ]
  • 11
  • [ 80149-80-0 ]
  • [ 161420-87-7 ]
  • [ 1268883-95-9 ]
  • 13
  • [ 89711-08-0 ]
  • [ 161420-87-7 ]
  • [ 1429403-84-8 ]
  • 14
  • [ 75141-72-9 ]
  • [ 161420-87-7 ]
  • (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-((S)-3-(tert-butoxy)-2-((tert-butoxycarbonyl)amino)propanamido)butanoic acid [ No CAS ]
  • 15
  • [ 16024-58-1 ]
  • [ 161420-87-7 ]
  • [ 1444302-35-5 ]
  • 16
  • [ 71989-35-0 ]
  • [ 86123-10-6 ]
  • [ 161420-87-7 ]
  • (2S)-2-[(9H-fluoren-9-ylmethoxy)carbonyl]amino}decanoic acid [ No CAS ]
  • C78H124N16O16 [ No CAS ]
  • 17
  • [ 701-97-3 ]
  • [ 35661-60-0 ]
  • [ 71989-31-6 ]
  • [ 71989-16-7 ]
  • [ 91000-69-0 ]
  • [ 135673-97-1 ]
  • [ 161420-87-7 ]
  • [ 76-05-1 ]
  • C43H76N12O8*C2HF3O2 [ No CAS ]
  • 18
  • [ 35661-60-0 ]
  • [ 71989-31-6 ]
  • [ 35661-40-6 ]
  • [ 71989-16-7 ]
  • [ 91000-69-0 ]
  • [ 161420-87-7 ]
  • [ 76-05-1 ]
  • [ 501-52-0 ]
  • C43H64N12O8*C2HF3O2 [ No CAS ]
  • 19
  • [ 35661-60-0 ]
  • [ 71989-31-6 ]
  • [ 35661-40-6 ]
  • [ 71989-16-7 ]
  • [ 91000-69-0 ]
  • [ 161420-87-7 ]
  • [ 76-05-1 ]
  • [ 501-52-0 ]
  • C43H64N12O8*C2HF3O2 [ No CAS ]
  • 20
  • [ 35661-60-0 ]
  • [ 71989-31-6 ]
  • [ 35661-40-6 ]
  • [ 91000-69-0 ]
  • [ 161420-87-7 ]
  • [ 76-05-1 ]
  • [ 501-52-0 ]
  • C45H70N14O7*C2HF3O2 [ No CAS ]
  • 22
  • [ 934992-90-2 ]
  • [ 161420-87-7 ]
  • C20H25N9O5 [ No CAS ]
  • 23
  • [ 625845-42-3 ]
  • [ 71989-14-5 ]
  • [ 64-19-7 ]
  • [ 161420-87-7 ]
  • [ 378247-75-7 ]
  • C40H53N7O11 [ No CAS ]
YieldReaction ConditionsOperation in experiment
General procedure: Synthesis of NH2-ACC-Rink Amide resin. Preparation of ACC wascarried out as described previously according to Maly et al.18 To glass reactionvessel, 1 eq (6.24 mmol, 13 g) of Rink AM resin was added and stirred gentlyonce per 10 min in DCM for 1 h, and then filtered and washed 3 times with DMF.Fmoc-protecting group was removed using 20% piperidine in DMF (5, 5, and25 min), filtered each time and washed with DMF (six times). Next, 2.50 eq of Fmoc-ACC-OH (15.6 mmol, 6.9 g) was preactivated with 2.50 eq HOBt monohydrate (15.6 mmol, 2.34 g) and 2.50 eq DICI (15.6 mmol, 2.0 ml) in DMFand mixture was added to the resin. Reaction was stirred gently for 24 h at room temperature. Resin was washed four times with DMF and reaction was repeatedusing 1.5 eq of above reagents to improve yield of ACC coupling to the resin. Afterreaction, resin was washed with DMF and Fmoc group was removed using 20%piperidine in DMF (5, 5, and 25 min), filtered and washed with DMF (six times). Synthesis of NH2-Asp(t-Bu)-ACC-Rink Amide resin. Next, 2.5 eqFmoc-Asp(t-Bu)-OH (15.6 mmol, 6.42 g) with 2.5 eq HATU (15.6 mmol, 5.93 g),2.5 eq collidine (15.6 mmol, 2.03 ml) in DMF were activated for 2 min and added tofilter cannula with 1 eq (6.24 mmol) NH2-ACC-resin and reaction was carried outfor 24 h. Next, resin was washed four times with DMF and reaction was repeatedusing 1.5 eq of above reagents. After washing with DMF, Fmoc-protecting groupwas removed using 20% piperidine in DMF (5, 5, and 25 min). Resin wasadditional washed with DCM (3 times) and MeOH (3 times) and dried over P2O5. Synthesis of individual optimized substrates. The 2.5 eqFmoc-P2-OH was preactivated with 2.5 eq HOBt and 2.5 eq DICI in DMF andadded to cartridge with 1 eq NH2-Asp(t-Bu)-ACC-resin (all substrates containedAsp at P1 position) and followed by gentle agitation for 3 h. Then, it was filteredand washed with DMF (six times). Fmoc-protecting group was removed using 20% piperidine in DMF (5, 5, and 25 min). Ninhydrin test was carried out each time aftercoupling and deprotection. A solution of 2.5 eq Fmoc-P3-OH, 2.5 eq HOBt, and2.5 eq DICI in DMF was added to the resin and the slurry was agitated for 3 h.After removal of the solution, the resin was washed with DMF (six times), andcoupling and deprotection of Fmoc-P4-OH was carried in identical conditions likeP2 position. N-terminus was protected with acetyl group using 5 eq AcOH, 5 eqHBTU, and 5 eq DIPEA in DMF as previous described. After solvent removal, theresin was washed with DMF (six times), DCM (three times), and MeOH (threetimes) dried over P2O5 and cleaved from the resin with a mixture of TFA/TIPS/H2O(%, v/v/v 95 : 2.5 : 2.5). The crude product was purified by HPLC and lyophilized.Its purity was confirmed by analytical HPLC. Each optimized substrate wasanalyzed using HRMS. Optimized substrates were dissolved in peptide gradeDMSO to 20mM concentration and stored at -80 Cuntil use.
  • 24
  • [ 161420-87-7 ]
  • Fmoc-Dab(propyl,Boc)-OH [ No CAS ]
  • 25
  • [ 161420-87-7 ]
  • C22H26N2O4 [ No CAS ]
  • 26
  • [ 123-72-8 ]
  • [ 161420-87-7 ]
  • C22H24N2O4 [ No CAS ]
  • 27
  • [ 35661-40-6 ]
  • [ 161420-87-7 ]
  • [ 158599-00-9 ]
  • Dab-F-F-O [ No CAS ]
  • 28
  • [ 35661-40-6 ]
  • [ 161420-87-7 ]
  • [ 158599-00-9 ]
  • Dab-O-F-O [ No CAS ]
  • 29
  • [ 35661-40-6 ]
  • [ 161420-87-7 ]
  • [ 158599-00-9 ]
  • F-O-F-Dab [ No CAS ]
  • 30
  • [ 35661-40-6 ]
  • [ 105047-45-8 ]
  • [ 161420-87-7 ]
  • K-F-F-Dab [ No CAS ]
  • 31
  • [ 35661-60-0 ]
  • [ 35661-40-6 ]
  • [ 71989-33-8 ]
  • [ 161420-87-7 ]
  • L-S-F-Dab [ No CAS ]
  • 32
  • H-Ala-2-chlorotrityl resin [ No CAS ]
  • [ 504-99-4 ]
  • [ 29022-11-5 ]
  • [ 68858-20-8 ]
  • [ 118904-37-3 ]
  • [ 104091-09-0 ]
  • [ 71989-23-6 ]
  • [ 73724-45-5 ]
  • [ 73724-45-5 ]
  • [ 35737-15-6 ]
  • [ 161420-87-7 ]
  • Fmoc-D-Dab(NH<SUB>2</SUB>)-OH [ No CAS ]
  • tridecaptin B1 [ No CAS ]
  • 33
  • H-Ala-2-chlorotrityl resin [ No CAS ]
  • [ 29022-11-5 ]
  • [ 68858-20-8 ]
  • [ 118904-37-3 ]
  • [ 104091-09-0 ]
  • [ 71989-23-6 ]
  • [ 73724-45-5 ]
  • [ 73724-45-5 ]
  • [ 35737-15-6 ]
  • [ 161420-87-7 ]
  • (R)-6-methyloctanoic acid [ No CAS ]
  • Fmoc-D-Dab(NH<SUB>2</SUB>)-OH [ No CAS ]
  • (6′R)-methyloctanoyl tridecaptin B1 [ No CAS ]
  • 34
  • H-Ala-2-chlorotrityl resin [ No CAS ]
  • [ 29022-11-5 ]
  • [ 68858-20-8 ]
  • [ 118904-37-3 ]
  • [ 104091-09-0 ]
  • [ 71989-23-6 ]
  • [ 73724-45-5 ]
  • [ 73724-45-5 ]
  • [ 35737-15-6 ]
  • [ 161420-87-7 ]
  • Fmoc-D-Dab(NH<SUB>2</SUB>)-OH [ No CAS ]
  • C58H95N17O18 [ No CAS ]
  • 35
  • H-Ala-2-chlorotrityl resin [ No CAS ]
  • [ 124-07-2 ]
  • [ 29022-11-5 ]
  • [ 68858-20-8 ]
  • [ 118904-37-3 ]
  • [ 104091-09-0 ]
  • [ 71989-23-6 ]
  • [ 73724-45-5 ]
  • [ 73724-45-5 ]
  • [ 35737-15-6 ]
  • [ 161420-87-7 ]
  • Fmoc-D-Dab(NH<SUB>2</SUB>)-OH [ No CAS ]
  • C66H109N17O19 [ No CAS ]
  • 36
  • [ 35661-39-3 ]
  • [ 71989-31-6 ]
  • [ 35737-15-6 ]
  • [ 73724-45-5 ]
  • [ 71989-31-6 ]
  • [ 132684-60-7 ]
  • [ 135673-97-1 ]
  • [ 161420-87-7 ]
  • [ 158599-00-9 ]
  • cyclo(-Trp-Ser-((S)-2-amino-3-cyclohexylpropanoyl)-((S)-2,4-diaminobutanoyl)-Orn-((S)-2,4-diaminobutanoyl)-((S)-2,4-diaminobutanoyl)-Trp-((S)-2,4-diaminobutanoyl)-((S)-2-amino-3,3-dimethylbutanoyl)-Ala-Ser-D-Pro-Pro-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
General procedure: [0798] In a dried flask, 2-chlorotritylchloride resin (polystyrene, 1% crosslinked; loading: 1.4 mmol/g) was swollen in dry CH2C12 for 30 mm (7 ml CH2C12 per g resin). A solution of 0.8 eq of the Fmoc-protected amino acid and 6 eq of DIPEA in dry CH2C12/DMF (4/1) (10 ml per g resin) was added. Afier shaking for 2-4 h at it the resin was filtered off and washed successively with CH2C12, DMF, CH2C12, DMF and CH2C12. Then a solution of dry CH2C12/MeOH/DIPEA (17:2:1) was added (10 ml perg resin).Afier shaking for 3x30 mm the resin was filtered off in a pre-weighed sinter funnel and washed successively with CH2C12, DMF, CH2C12, MeOH, CH2C12, MeOH, CH2C12 (2x) and Et20 (2x). The resin was dried under high vacuum overnight. The final mass of resin was calculated before the qualitative control.[0803] After assembly of the linear peptide, the resin was suspended in 1 ml of 1% TFA in CH2C12 (v/v; 0.14 mmol) for 3 minutes and filtered, and the filtrate was neutralized with 1 ml of 20% DIPEA in CH2C12 (v/v; 1.15 mmol). This procedure was repeated four times to ensure completion of the cleavage. The resin was washed three times with 1 ml of CH2C12. The CH2C12 layers containing product were evaporated to dryness.10804] The fully protected linear peptide was solubilised in8 ml of dry DMF. Then 2 eq. of HA11J and 2. eq. of HOAt in dry DMF (1-2 ml) and 4 eq. of DIPEA in dry DMF (1-2 ml) were added to the peptide, followed by stirring for ca. 16 h. The volatiles were removed by evaporation. The crude cyclic peptide was dissolved in 7 ml of CH2C12 and washed three times with 4.5 ml 10% acetonitrile in water (v/v). The CH2C12 layer was then evaporated to dryness.10805] To fully deprotect the peptide, 7 ml of cleavage cocktail TFADODT/thioanisol/H20 (87.5:2.5:5:5) were added, and the mixture was kept for 2.5-4 hat room tempera- tare until the reaction was completed. The reaction mixture was evaporated close to dryness and the peptide precipitated with 7 ml of cold Et20. The precipitate was washed 3 times with 4 ml of cold Et20.
 

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