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[ CAS No. 20806-43-3 ] {[proInfo.proName]}

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Chemical Structure| 20806-43-3
Chemical Structure| 20806-43-3
Structure of 20806-43-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 20806-43-3 ]

CAS No. :20806-43-3 MDL No. :MFCD00022029
Formula : C18H19NO5 Boiling Point : -
Linear Structure Formula :- InChI Key :CYYRLHUAMWRBHC-INIZCTEOSA-N
M.W : 329.35 Pubchem ID :6993425
Synonyms :

Calculated chemistry of [ 20806-43-3 ]

Physicochemical Properties

Num. heavy atoms : 24
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.22
Num. rotatable bonds : 10
Num. H-bond acceptors : 5.0
Num. H-bond donors : 2.0
Molar Refractivity : 87.26
TPSA : 84.86 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) : -6.6 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.4
Log Po/w (XLOGP3) : 2.41
Log Po/w (WLOGP) : 2.28
Log Po/w (MLOGP) : 1.9
Log Po/w (SILICOS-IT) : 2.32
Consensus Log Po/w : 2.26

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.11
Solubility : 0.256 mg/ml ; 0.000776 mol/l
Class : Soluble
Log S (Ali) : -3.83
Solubility : 0.0483 mg/ml ; 0.000147 mol/l
Class : Soluble
Log S (SILICOS-IT) : -5.01
Solubility : 0.00325 mg/ml ; 0.00000986 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.38

Safety of [ 20806-43-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 20806-43-3 ]

* 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 [ 20806-43-3 ]
  • Downstream synthetic route of [ 20806-43-3 ]

[ 20806-43-3 ] Synthesis Path-Upstream   1~19

  • 1
  • [ 20806-43-3 ]
  • [ 4726-96-9 ]
Reference: [1] Tetrahedron, 1998, vol. 54, # 46, p. 13981 - 13996
[2] Zeitschrift fuer Chemie (Stuttgart, Germany), 1981, vol. 21, # 5, p. 188
  • 2
  • [ 20806-43-3 ]
  • [ 56-45-1 ]
  • [ 4726-96-9 ]
Reference: [1] Tetrahedron, 1998, vol. 54, # 46, p. 13981 - 13996
  • 3
  • [ 4726-96-9 ]
  • [ 31139-36-3 ]
  • [ 20806-43-3 ]
YieldReaction ConditionsOperation in experiment
95% With sodium carbonate In 1,4-dioxane; water To a stirred solution of O-benzyl-L-serine (25.0 g, 128 mmole) in water (200 ml) and dioxane (100 ml) was added sodium carbonate (7.46 g, 70 mmole) at room temperature.
A solution of dibenzyldicarbonate (36.1 g, 126 mmole) in dioxane (100 ml) was added dropwise and the mixture stirred for 18 hours.
Dioxane was evaporated under vacuum and the aqueous residue extracted with diethyl ether.
Evaporation of the dried (Na2 SO4) extracts under vacuum gave a white solid which was washed with hexane to yield crude N-benzyloxycarbonyl-O-benzyl-L-serine (39.57 g, 95percent).
95% With sodium carbonate In 1,4-dioxane; water To a stirred solution of O-benzyl-L-serine (25.0 g, 128 mmole) in water (200 ml) and dioxane (100 ml) was added sodium carbonate (7.46 g, 70 mmole) at room temperature.
A solution of dibenzyldicarbonate (36.1 g, 126 mmole) in dioxane (100 ml) was added dropwise and the mixture stirred for 18 hours.
Dioxane was evaporated under vacuum and the aqueous residue extracted with diethyl ether.
Evaporation of the dried (Na2SO4) extracts under vacuum gave a white solid which was washed with hexane to yield crude N-benzyloxycarbonyl-O-benzyl-L-serine (39.57 g, 95percent).
Reference: [1] Liebigs Annalen der Chemie, 1994, # 6, p. 641 - 644
[2] Patent: US5030654, 1991, A,
[3] Patent: EP274234, 1991, B1,
  • 4
  • [ 4726-96-9 ]
  • [ 501-53-1 ]
  • [ 20806-43-3 ]
Reference: [1] Journal of the American Chemical Society, 1991, vol. 113, # 7, p. 2722 - 2729
[2] Bulletin of the Chemical Society of Japan, 1956, vol. 29, p. 488
  • 5
  • [ 394210-41-4 ]
  • [ 20806-43-3 ]
Reference: [1] Journal of the American Chemical Society, 2001, vol. 123, # 50, p. 12696 - 12697
  • 6
  • [ 98695-13-7 ]
  • [ 20806-43-3 ]
  • [ 20806-42-2 ]
Reference: [1] Patent: EP2799422, 2014, A1, . Location in patent: Paragraph 0069; 0070
  • 7
  • [ 98695-13-7 ]
  • [ 20806-43-3 ]
Reference: [1] Organic Letters, 2012, vol. 14, # 12, p. 3194 - 3197
  • 8
  • [ 5445-44-3 ]
  • [ 20806-43-3 ]
Reference: [1] Journal of the American Chemical Society, 2001, vol. 123, # 50, p. 12696 - 12697
[2] Bulletin of the Chemical Society of Japan, 1956, vol. 29, p. 488
[3] Il Farmaco; edizione scientifica, 1968, vol. 23, # 10, p. 945 - 948
  • 9
  • [ 83824-86-6 ]
  • [ 20806-43-3 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1982, vol. 55, # 9, p. 3049 - 3050
  • 10
  • [ 118867-04-2 ]
  • [ 20806-43-3 ]
Reference: [1] Tetrahedron Letters, 1992, vol. 33, # 37, p. 5441 - 5444
  • 11
  • [ 4726-96-9 ]
  • [ 75315-63-8 ]
  • [ 20806-43-3 ]
Reference: [1] Tetrahedron, 1999, vol. 55, # 16, p. 5157 - 5170
  • 12
  • [ 22831-98-7 ]
  • [ 20806-43-3 ]
Reference: [1] Journal of the American Chemical Society, 2001, vol. 123, # 50, p. 12696 - 12697
  • 13
  • [ 1145-80-8 ]
  • [ 100-39-0 ]
  • [ 20806-43-3 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1980, vol. 28, # 9, p. 2699 - 2706
[2] European Journal of Medicinal Chemistry, 1998, vol. 33, # 7-8, p. 635 - 645
  • 14
  • [ 83824-80-0 ]
  • [ 20806-43-3 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1982, vol. 55, # 9, p. 3049 - 3050
  • 15
  • [ 501-53-1 ]
  • [ 20806-43-3 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1982, vol. 55, # 9, p. 3049 - 3050
  • 16
  • [ 35436-77-2 ]
  • [ 20806-43-3 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1956, vol. 29, p. 488
  • 17
  • [ 23680-31-1 ]
  • [ 501-53-1 ]
  • [ 20806-43-3 ]
Reference: [1] Journal of Medicinal Chemistry, 1979, vol. 22, p. 935 - 943
  • 18
  • [ 1145-80-8 ]
  • [ 20806-43-3 ]
Reference: [1] Tetrahedron, 1985, vol. 41, # 10, p. 1939 - 1944
  • 19
  • [ 20806-39-7 ]
  • [ 20806-43-3 ]
Reference: [1] Il Farmaco; edizione scientifica, 1968, vol. 23, # 10, p. 945 - 948
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