Home Cart 0 Sign in  

[ CAS No. 32159-21-0 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 32159-21-0
Chemical Structure| 32159-21-0
Structure of 32159-21-0 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 32159-21-0 ]

Related Doc. of [ 32159-21-0 ]

Alternatived Products of [ 32159-21-0 ]

Product Details of [ 32159-21-0 ]

CAS No. :32159-21-0 MDL No. :MFCD00037352
Formula : C13H13NO5 Boiling Point : -
Linear Structure Formula :- InChI Key :VHSFUGXCSGOKJX-JTQLQIEISA-N
M.W : 263.25 Pubchem ID :637648
Synonyms :

Calculated chemistry of [ 32159-21-0 ]

Physicochemical Properties

Num. heavy atoms : 19
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.31
Num. rotatable bonds : 5
Num. H-bond acceptors : 5.0
Num. H-bond donors : 1.0
Molar Refractivity : 68.59
TPSA : 83.91 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.12 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.58
Log Po/w (XLOGP3) : 1.1
Log Po/w (WLOGP) : 0.87
Log Po/w (MLOGP) : 0.41
Log Po/w (SILICOS-IT) : 0.73
Consensus Log Po/w : 0.94

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.07
Solubility : 2.25 mg/ml ; 0.00853 mol/l
Class : Soluble
Log S (Ali) : -2.45
Solubility : 0.924 mg/ml ; 0.00351 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.97
Solubility : 2.81 mg/ml ; 0.0107 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.71

Safety of [ 32159-21-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 32159-21-0 ]

* 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 [ 32159-21-0 ]
  • Downstream synthetic route of [ 32159-21-0 ]

[ 32159-21-0 ] Synthesis Path-Upstream   1~18

  • 1
  • [ 32159-21-0 ]
  • [ 79640-72-5 ]
Reference: [1] Journal of Medicinal Chemistry, 1991, vol. 34, # 3, p. 956 - 968
  • 2
  • [ 32159-21-0 ]
  • [ 5891-45-2 ]
Reference: [1] Journal of Medicinal Chemistry, 1991, vol. 34, # 3, p. 956 - 968
[2] Journal of Medicinal Chemistry, 1990, vol. 33, # 2, p. 461 - 464
  • 3
  • [ 497-19-8 ]
  • [ 501-53-1 ]
  • [ 98-79-3 ]
  • [ 32159-21-0 ]
Reference: [1] Patent: US6034058, 2000, A,
  • 4
  • [ 4124-76-9 ]
  • [ 32159-21-0 ]
Reference: [1] Journal of Medicinal Chemistry, 1991, vol. 34, # 3, p. 956 - 968
  • 5
  • [ 1155-62-0 ]
  • [ 32159-21-0 ]
Reference: [1] Journal of Medicinal Chemistry, 1990, vol. 33, # 2, p. 461 - 464
[2] Tetrahedron, 1989, vol. 45, # 23, p. 7459 - 7468
[3] Journal of Medicinal Chemistry, 1991, vol. 34, # 3, p. 956 - 968
  • 6
  • [ 501-53-1 ]
  • [ 98-79-3 ]
  • [ 32159-21-0 ]
Reference: [1] Chemical & Pharmaceutical Bulletin, 1981, vol. 29, # 9, p. 2699 - 2701
[2] Pharmazie, 1993, vol. 48, # 4, p. 260 - 262
  • 7
  • [ 4124-76-9 ]
  • [ 1155-62-0 ]
  • [ 32159-21-0 ]
Reference: [1] Tetrahedron Asymmetry, 2006, vol. 17, # 14, p. 2120 - 2125
[2] Tetrahedron Asymmetry, 2006, vol. 17, # 14, p. 2120 - 2125
  • 8
  • [ 1003-09-4 ]
  • [ 4124-76-9 ]
  • [ 1155-62-0 ]
  • [ 32159-21-0 ]
Reference: [1] Tetrahedron Asymmetry, 2006, vol. 17, # 14, p. 2120 - 2125
  • 9
  • [ 109-65-9 ]
  • [ 4124-76-9 ]
  • [ 1155-62-0 ]
  • [ 32159-21-0 ]
Reference: [1] Tetrahedron Asymmetry, 2006, vol. 17, # 14, p. 2120 - 2125
  • 10
  • [ 2398-37-0 ]
  • [ 4124-76-9 ]
  • [ 1155-62-0 ]
  • [ 32159-21-0 ]
Reference: [1] Tetrahedron Asymmetry, 2006, vol. 17, # 14, p. 2120 - 2125
  • 11
  • [ 111-25-1 ]
  • [ 4124-76-9 ]
  • [ 1155-62-0 ]
  • [ 32159-21-0 ]
Reference: [1] Tetrahedron Asymmetry, 2006, vol. 17, # 14, p. 2120 - 2125
  • 12
  • [ 100-59-4 ]
  • [ 4124-76-9 ]
  • [ 1155-62-0 ]
  • [ 32159-21-0 ]
Reference: [1] Tetrahedron Asymmetry, 2006, vol. 17, # 14, p. 2120 - 2125
  • 13
  • [ 591-51-5 ]
  • [ 4124-76-9 ]
  • [ 1155-62-0 ]
  • [ 32159-21-0 ]
Reference: [1] Tetrahedron Asymmetry, 2006, vol. 17, # 14, p. 2120 - 2125
  • 14
  • [ 32159-21-0 ]
  • [ 115-11-7 ]
  • [ 81470-51-1 ]
YieldReaction ConditionsOperation in experiment
67%
Stage #1: With sulfuric acid In dichloromethane at 20℃; Cooling with ice
Stage #2: With sodium carbonate In dichloromethane; water
Reference Example 1; (2S,5S)-1-Benzyl 2-tert-butyl 5-hydroxypiperidine-1,2-dicarboxylate (A)Step 1: (S)-1-Benzyl 2-tert-butyl 5-oxopyrrolidine-1,2-dicarboxylate 100 g of (S)-1-(benzyloxycarbonyl)-5-oxopyrrolidine-2-carboxylic acid was dissolved in dehydrated dichloromethane (2 L), and under ice cooling, concentrated sulfuric acid (10 mL) and 213 g of isobutene were added, followed by stirring overnight at +20° C. or less. The reaction mixture was added to cold aqueous sodium carbonate solution while paying attention to effervescence, followed by liquid separation of the organic phase, washing with saturated brine and drying over anhydrous magnesium sulfate, and the solvent was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (hexane/ethyl acetate=7/3), and crystallized with hexane/ethyl acetate to afford 80 g of the title compound as a colorless crystalline powder (yield 67percent). Enantiomeric excess: 99.9percent ee or more (CHIRALPAK AD-H, 4.6.x.150 mm, UV 210 nm, hexane/ethanol=2/1, flow rate 1 mL/min., retention time 4.2 min.).[α]20D -43.3° (c 0.52 in CHCl3), according to Non-Patent Document 4 -41.81° (c 6.71, CHCl3); 1H NMR (400 MHz, CDCl3, δ): 1.39 (s, 9H), 2.04 (m, 1H), 2.32 (m, 1H), 2.51 (ddd, J=17.6, 9.5, 3.2 Hz, 1H), 2.62 (ddd, J=176, 10.5, 9.5 Hz, 1H), 4.55 (dd, J=9.5, 2.7 Hz, 1H), 5.25 J=12.2 Hz, 1H), 5.30 (d, J=12.2 Hz, 1H), 7.26-7.41 (m, 5H);
67% With sulfuric acid In dichloromethane at 20℃; Cooling with ice 100 g of (S)-1-(benzyloxycarbonyl)-5-oxopyrrolidine-2-carboxylic acid was dissolved in dehydrated dichloromethane (2 L), and under ice cooling, concentrated sulfuric acid (10 mL) and 213 g of isobutene were added, followed by stirring overnight at +20°C or less.
The reaction mixture was added to cold aqueous sodium carbonate solution while paying attention to effervescence, followed by liquid separation of the organic phase, washing with saturated brine and drying over anhydrous magnesium sulfate, and the solvent was concentrated under reduced pressure.
The residue was subjected to silica gel column chromatography (hexane/ethyl acetate=7/3), and crystallized with hexane/ethyl acetate to afford 80 g of the title compound as a colorless crystalline powder (yield 67percent).
Enantiomeric excess: 99.9percent ee or more (CHIRALPAK AD-H, 4.6 x 150 mm, UV 210 nm, hexane/ethanol=2/1, flow rate 1 mL/min., retention time 4.2 min.).
[α]20D-43.3°(c 0.52 in CHCl3), according to Non-Patent Document 4 -41.8°(c 6.71, CHCl3); 1H NMR (400 MHz, CDCl3, δ): 1.39 (s, 9H), 2.04 (m, 1H), 2.32 (m, 1H), 2.51 (ddd, J = 17.6, 9.5, 3.2 Hz, 1H), 2.62 (ddd, J = 17.6, 10.5, 9.5 Hz, 1H), 4.55 (dd, J = 9.5, 2.7 Hz, 1H), 5.25 (d, J = 12.2 Hz, 1H), 5.30 (d, J = 12.2 Hz, 1H), 7.26-7.41 (m, 5H); MS m/z: 320 (M+1).
67% With sulfuric acid In dichloromethane at 20℃; Cooling with ice Step 1: (S)-1-Benzyl 2-tert-butyl 5-oxopyrrolidine-1,2-dicarboxylate [0239] (S)-1-(Benzyloxycarbonyl)-5-oxopyrrolidine-2-carboxylic acid (100 g) was dissolved in dehydrated methylene chloride (2 L), and under ice cooling, concentrated sulfuric acid (10 mL) and isobutene (213 g) were added, followed by stirring overnight at +20 °C or less. The reaction mixture was added to cold aqueous sodium carbonate solution while paying attention to effervescence, followed by liquid separation of the organic phase, washing with saturated brine and drying over anhydrous magnesium sulfate, then the solvent was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (hexane/ethyl acetate = 7/3), and crystallized with hexane/ethyl acetate to afford 80 g of the title compound as a colorless crystalline powder (yield 67percent). Enantiomeric excess 99.9percent ee or more (CHIRALPAK AD-H, 4.6 x 150 mm, UV 210 nm, hexane/ethanol = 2/1, flow rate 1 mL/min., retention time 4.2 min.). [α]20D -43.3° (c 0.52 in CHCl3), according to Non-Patent Document [Journal of Medicinal Chemistry 1991, 34(3), 956-968. Dolence, EK.; Lin, CE.; Miller, MJ.; Payne, SM. "Synthesis and siderophore activity of albomycin-like peptides derived from N5-acetyl-N5-hydroxy-L-ornithine"] -41.8° (c 6.71, CHCl3); 1H NMR (400 MHz, CDCl3) δ 1.39 (s, 9H), 2.04 (m, 1H), 2.32 (m, 1H), 2.51 (ddd, J = 17.6, 9.5, 3.2 Hz, 1H), 2.62 (ddd, J = 17.6, 10.5, 9.5 Hz, 1H), 4.55 (dd, J = 9.5, 2.7 Hz, 1H), 5.25 (d, J = 12.2 Hz, 1H), 5.30 (d, J = 12.2 Hz, 1H), 7.26-7.41 (m, 5H); MS m/z 320 (M+H).
Reference: [1] Journal of Organic Chemistry, 1992, vol. 57, # 6, p. 1920 - 1924
[2] Patent: US2012/165533, 2012, A1, . Location in patent: Page/Page column 21
[3] Patent: EP2657234, 2013, A1, . Location in patent: Paragraph 0187; 0188
[4] Patent: EP2857401, 2015, A1, . Location in patent: Paragraph 0239
  • 15
  • [ 32159-21-0 ]
  • [ 81470-51-1 ]
YieldReaction ConditionsOperation in experiment
79% With perchloric acid In water at 20℃; for 16 h; 70percent Aqueous perchloric acid (1.65ml, ca. 0.065mol) was dropwised to a suspension of compound11int-BuOAc (200ml) at room temperature, and the resulting mixture was stirred for 16h. Saturated aqueous sodium bicarbonate (300ml) was added to the solution gradually, and most of thet-BuOAc in the mixture was removed in vacuo. The residue was extracted with chloroform, and the organic layer was washed with brine. After drying over magnesium sulfate, the mixture was filtered, and the solvent was removed in vacuo to give the colorless oil (13.9g, 79percent yield);1H NMR (400MHz, CDCl3)δ: 1.39 (9H, s), 2.01–2.08 (1H, m), 2.27–2.36 (1H, m), 2.45–2.53 (1H, m), 2.59–2.68 (1H, m), 4.55 (1H, dd,J=9.4, 2.6Hz), 5.25 (1H, d,J=12.4Hz), 5.30 (1H, d,J=12.2Hz), 7.31–7.41 (5H, m); ESI/MS:m/z=342 (M+Na).
Reference: [1] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 14, p. 4319 - 4331
  • 16
  • [ 540-88-5 ]
  • [ 32159-21-0 ]
  • [ 81470-51-1 ]
Reference: [1] Journal of Medicinal Chemistry, 1990, vol. 33, # 2, p. 461 - 464
[2] Journal of Medicinal Chemistry, 1991, vol. 34, # 3, p. 956 - 968
  • 17
  • [ 32159-21-0 ]
  • [ 75-65-0 ]
  • [ 81470-51-1 ]
Reference: [1] Tetrahedron, 1989, vol. 45, # 23, p. 7459 - 7468
  • 18
  • [ 32159-21-0 ]
  • [ 154307-84-3 ]
Reference: [1] Patent: EP2857401, 2015, A1,
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 32159-21-0 ]

Amino Acid Derivatives

Chemical Structure| 1148-11-4

[ 1148-11-4 ]

Z-Pro-OH

Similarity: 0.93

Chemical Structure| 6404-31-5

[ 6404-31-5 ]

((Benzyloxy)carbonyl)-D-proline

Similarity: 0.93

Chemical Structure| 5618-96-2

[ 5618-96-2 ]

Z-DL-Pro-OH

Similarity: 0.93

Chemical Structure| 400626-71-3

[ 400626-71-3 ]

(R)-2-Benzyl 1-tert-butyl 5-oxopyrrolidine-1,2-dicarboxylate

Similarity: 0.93

Chemical Structure| 81470-51-1

[ 81470-51-1 ]

Z-Pyr-OtBu

Similarity: 0.93