Home Cart 0 Sign in  

[ CAS No. 71989-31-6 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 71989-31-6
Chemical Structure| 71989-31-6
Structure of 71989-31-6 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 71989-31-6 ]

Related Doc. of [ 71989-31-6 ]

Alternatived Products of [ 71989-31-6 ]

Product Details of [ 71989-31-6 ]

CAS No. :71989-31-6 MDL No. :MFCD00037122
Formula : C20H19NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :ZPGDWQNBZYOZTI-SFHVURJKSA-N
M.W :337.37 Pubchem ID :688135
Synonyms :
Fmoc-Pro-OH

Calculated chemistry of [ 71989-31-6 ]

Physicochemical Properties

Num. heavy atoms : 25
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.3
Num. rotatable bonds : 5
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 96.68
TPSA : 66.84 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.97 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.26
Log Po/w (XLOGP3) : 3.36
Log Po/w (WLOGP) : 3.1
Log Po/w (MLOGP) : 2.78
Log Po/w (SILICOS-IT) : 2.66
Consensus Log Po/w : 2.83

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -4.07
Solubility : 0.0285 mg/ml ; 0.0000844 mol/l
Class : Moderately soluble
Log S (Ali) : -4.44
Solubility : 0.0122 mg/ml ; 0.0000362 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -4.61
Solubility : 0.00834 mg/ml ; 0.0000247 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 3.64

Safety of [ 71989-31-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 71989-31-6 ]

* 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.

  • Upstream synthesis route of [ 71989-31-6 ]
  • Downstream synthetic route of [ 71989-31-6 ]

[ 71989-31-6 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 71989-31-6 ]
  • [ 100-52-7 ]
  • [ 31795-93-4 ]
Reference: [1] Tetrahedron Letters, 1996, vol. 37, # 27, p. 4819 - 4822
  • 2
  • [ 29022-11-5 ]
  • [ 35661-60-0 ]
  • [ 1403834-74-1 ]
  • [ 71989-31-6 ]
  • [ 71989-23-6 ]
  • [ 71989-38-3 ]
  • [ 132388-59-1 ]
  • [ 132327-80-1 ]
  • [ 50-56-6 ]
Reference: [1] Organic Letters, 2013, vol. 15, # 3, p. 616 - 619
  • 3
  • [ 29022-11-5 ]
  • [ 35661-60-0 ]
  • [ 71989-31-6 ]
  • [ 71989-23-6 ]
  • [ 71989-38-3 ]
  • [ 103213-32-7 ]
  • [ 132388-59-1 ]
  • [ 132327-80-1 ]
  • [ 50-56-6 ]
Reference: [1] Organic Letters, 2018, vol. 20, # 19, p. 6074 - 6078
  • 4
  • [ 35661-60-0 ]
  • [ 67436-13-9 ]
  • [ 115057-30-2 ]
  • [ 71989-31-6 ]
  • [ 50-56-6 ]
Reference: [1] Tetrahedron Letters, 1987, vol. 28, # 46, p. 5651 - 5654
  • 5
  • [ 68858-20-8 ]
  • [ 71989-31-6 ]
  • [ 71989-14-5 ]
  • [ 71989-23-6 ]
  • [ 71989-38-3 ]
  • [ 109425-51-6 ]
  • [ 4474-91-3 ]
Reference: [1] European Journal of Inorganic Chemistry, 2016, vol. 2016, # 35, p. 5427 - 5434
  • 6
  • [ 24424-99-5 ]
  • [ 71989-31-6 ]
  • [ 15401-08-8 ]
Reference: [1] Chemistry and Biodiversity, 2013, vol. 10, # 1, p. 1 - 38
  • 7
  • [ 71989-31-6 ]
  • [ 129223-22-9 ]
Reference: [1] Chirality, 2012, vol. 24, # 4, p. 329 - 338
  • 8
  • [ 56-91-7 ]
  • [ 71989-31-6 ]
  • [ 164470-64-8 ]
YieldReaction ConditionsOperation in experiment
90% With sodium hydrogencarbonate In 1,4-dioxane; water at 20℃; for 2 h; (4-aminomethyl)-benzoic acid (4.9 g, 1. 1 equiv. ) was dissolved in 5percent NaHCO3 150 ml in water and stirred. N- (9- Fluorenylmethoxycarbonyl) -L-proline (Fmoc, 1 equiv. , lOg) was dissolved in an equivalent amount of dioxane and added. The reaction was allowed to stir at room temperature. After two hours, 10percent citric acid in water 75 ml was added. A white solid precipitated upon addition. The solid was washed filtered and washed with hexane. The solid was dissolved in THF and allowed to dry overnight over MGSO. The following day, the solution was filtered, crystallized from THF and hexane, and placed under a drying vacuum (90percent yield). ESIMS: (M+H) + Calcd, 373.1 ; Found, 374.1.
Reference: [1] Journal of the American Chemical Society, 2003, vol. 125, # 39, p. 11804 - 11805
[2] Patent: WO2004/99106, 2004, A2, . Location in patent: Page 18-19; 27-28
  • 9
  • [ 71989-31-6 ]
  • [ 193693-60-6 ]
Reference: [1] Helvetica Chimica Acta, 1998, vol. 81, # 1, p. 59 - 65
  • 10
  • [ 71989-31-6 ]
  • [ 148625-77-8 ]
YieldReaction ConditionsOperation in experiment
95%
Stage #1: With sodium tetrahydroborate In tetrahydrofuran at 0℃; for 1 h; Inert atmosphere
Stage #2: With boron trifluoride diethyl etherate In tetrahydrofuran at 0℃; for 18 h; Inert atmosphere
General procedure: (S)- or (R)-Fmoc proline (4.58g, 13.6mmol) in anhydrous THF (125mL) was placed in a round-bottomed flask with magnetic stirrer and under inert atmosphere (N2). The resulting solution was cooled to 0°C, before the slow addition of NaBH4 (0.82g, 21.7mmol). The reaction mixture was stirred during 60min at 0°C, and then 3.4mL (3.85g, 27.1mmol) of boron trifluoride diethyl etherate were added dropwise, and stirring was continued for 18h at 0°C. The reaction progress was monitored by TLC (CH2Cl2/EtOAc 70:30). Thirty milliliters of water were added at 0°C and the resulting mixture was stirred for 30min. THF was evaporated in vacuo, the remaining aqueous layer was extracted with EtOAc (3×100mL) and the combined organic fractions were washed with brine, dried over anhydrous Na2SO4 and filtered. The solvent was evaporated under reduced pressure and the crude product was purified by flash chromatography, using gradient CH2Cl2:EtOAc (95:5)→(85:15) as eluent. The product (hard gum) was precipitated with cold hexane to obtain a white powder, which was stored at−15°C.
Reference: [1] Tetrahedron, 2017, vol. 73, # 32, p. 4707 - 4718
[2] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 14, p. 3752 - 3755
[3] Journal of Organic Chemistry, 2001, vol. 66, # 25, p. 8454 - 8462
[4] Journal of Organic Chemistry, 2009, vol. 74, # 15, p. 5260 - 5266
  • 11
  • [ 71989-31-6 ]
  • [ 187223-15-0 ]
Reference: [1] Patent: WO2016/207912, 2016, A1,
  • 12
  • [ 71989-31-6 ]
  • [ 215178-45-3 ]
YieldReaction ConditionsOperation in experiment
93%
Stage #1: With sodium tetrahydroborate In tetrahydrofuran at 0℃; for 1 h; Inert atmosphere
Stage #2: With boron trifluoride diethyl etherate In tetrahydrofuran at 0℃; for 18 h; Inert atmosphere
General procedure: (S)- or (R)-Fmoc proline (4.58g, 13.6mmol) in anhydrous THF (125mL) was placed in a round-bottomed flask with magnetic stirrer and under inert atmosphere (N2). The resulting solution was cooled to 0°C, before the slow addition of NaBH4 (0.82g, 21.7mmol). The reaction mixture was stirred during 60min at 0°C, and then 3.4mL (3.85g, 27.1mmol) of boron trifluoride diethyl etherate were added dropwise, and stirring was continued for 18h at 0°C. The reaction progress was monitored by TLC (CH2Cl2/EtOAc 70:30). Thirty milliliters of water were added at 0°C and the resulting mixture was stirred for 30min. THF was evaporated in vacuo, the remaining aqueous layer was extracted with EtOAc (3×100mL) and the combined organic fractions were washed with brine, dried over anhydrous Na2SO4 and filtered. The solvent was evaporated under reduced pressure and the crude product was purified by flash chromatography, using gradient CH2Cl2:EtOAc (95:5)→(85:15) as eluent. The product (hard gum) was precipitated with cold hexane to obtain a white powder, which was stored at−15°C.
Reference: [1] Tetrahedron, 2017, vol. 73, # 32, p. 4707 - 4718
Same Skeleton Products
Historical Records

Pharmaceutical Intermediates of
[ 71989-31-6 ]

Davunetide Intermediates

Chemical Structure| 71989-23-6

[ 71989-23-6 ]

Fmoc-Ile-OH

Chemical Structure| 71989-33-8

[ 71989-33-8 ]

Fmoc-Ser(tBu)-OH

Chemical Structure| 132327-80-1

[ 132327-80-1 ]

Fmoc-Gln(Trt)-OH

Chemical Structure| 68858-20-8

[ 68858-20-8 ]

Fmoc-Val-OH

Chemical Structure| 35661-39-3

[ 35661-39-3 ]

Fmoc-Ala-OH

Disomotide Intermediates

Chemical Structure| 71989-23-6

[ 71989-23-6 ]

Fmoc-Ile-OH

Similar Product of
[ 71989-31-6 ]

Chemical Structure| 204523-24-0

A1269749[ 204523-24-0 ]

Fmoc-Pro-OH-15N

Reason: Stable Isotope

Related Functional Groups of
[ 71989-31-6 ]

Amino Acid Derivatives

Chemical Structure| 1093651-96-7

[ 1093651-96-7 ]

(2S,4R)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)-4-phenylpyrrolidine-2-carboxylic acid

Similarity: 0.99

Chemical Structure| 130309-37-4

[ 130309-37-4 ]

(2S,3aS,7aS)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)octahydro-1H-indole-2-carboxylic acid

Similarity: 0.99

Chemical Structure| 167275-47-0

[ 167275-47-0 ]

(S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)-2-methylpyrrolidine-2-carboxylic acid

Similarity: 0.97

Chemical Structure| 101555-62-8

[ 101555-62-8 ]

Fmoc-D-Pro-OH

Similarity: 0.97

Chemical Structure| 1217482-47-7

[ 1217482-47-7 ]

(R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)hexanoic acid

Similarity: 0.97