[ CAS No. 142217-80-9 ] {[proInfo.proName]}

Name: 142217-80-9|6-(Benzyloxy)-9-((1S,3S)-4-(benzyloxy)-3-((benzyloxy)methyl)-2-methylenecyclopentyl)-N-((4-methoxyphenyl)diphenylmethyl)-9H-purin-2-amine|95%
Brand: Ambeed
SKU: A100394
Price: 14.0 USD
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2D 3D

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Quality Control of [ 142217-80-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 142217-80-9 ]

SDS Specification

Alternatived Products of [ 142217-80-9 ]

Product Details of [ 142217-80-9 ]

CAS No. :	142217-80-9	MDL No. :	MFCD09750979
Formula :	C₅₃H₄₉N₅O₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	819.99	Pubchem ID :	-
Synonyms :

Calculated chemistry of [ 142217-80-9 ]

Physicochemical Properties

Num. heavy atoms :	62
Num. arom. heavy atoms :	45
Fraction Csp3 :	0.19
Num. rotatable bonds :	17
Num. H-bond acceptors :	7.0
Num. H-bond donors :	1.0
Molar Refractivity :	243.72
TPSA :	92.55 Å²

Pharmacokinetics

GI absorption :	Low
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) :	-4.09 cm/s

Lipophilicity

Log Po/w (iLOGP) :	6.0
Log Po/w (XLOGP3) :	10.16
Log Po/w (WLOGP) :	9.98
Log Po/w (MLOGP) :	5.42
Log Po/w (SILICOS-IT) :	9.31
Consensus Log Po/w :	8.17

Druglikeness

Lipinski :	2.0
Ghose :	None
Veber :	1.0
Egan :	1.0
Muegge :	4.0
Bioavailability Score :	0.17

Water Solubility

Log S (ESOL) :	-10.74
Solubility :	0.0000000149 mg/ml ; 0.0 mol/l
Class :	Insoluble
Log S (Ali) :	-12.04
Solubility :	0.0000000008 mg/ml ; 0.0 mol/l
Class :	Insoluble
Log S (SILICOS-IT) :	-17.96
Solubility :	8.97e-16 mg/ml ; 1.09e-18 mol/l
Class :	Insoluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	3.0
Synthetic accessibility :	6.87

Safety of [ 142217-80-9 ]

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

Application In Synthesis of [ 142217-80-9 ]

* 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 [ 142217-80-9 ]
Downstream synthetic route of [ 142217-80-9 ]

[ 142217-80-9 ] Synthesis Path-Upstream 1~10

1
[ 142217-79-6 ]
[ 142217-80-9 ]

Yield	Reaction Conditions	Operation in experiment
88%	With hydrogenchloride; titanium tetrachloride; zinc In tetrahydrofuran; dichloromethane; water at -30 - 20℃; Inert atmosphere; Sealed tube; Molecular sieve	Step (1) Preparation of intermediate IX, in a sealed nitrogen-filled 20L reaction bottle, 3.8kg of zinc powder and 10wtpercent hydrochloric acid (12.5L) were sequentially added, stirred at room temperature for 10-15min, suction filtered, washed with purified water to neutral, Wash with 3.0L ethanol, 4.5L tetrahydrofuranPolyester, 40 ± 2 ° C vacuum drying 4-4.5h to obtain about 3kg activated zinc powder. The activated zinc powder is sealed and stored under vacuum.In a 100L reactor, evacuate, replace N2, add 40L of dry (type A molecular sieve drying) tetrahydrofuran, add dry activated 3kg zinc powder and 1.3L of dibromomethane with stirring, and cool the mixture to -70~-55 °C And then drop1140 ml of titanium tetrachloride was added dropwise, stirred for 1 h, then warmed up, reacted for 48 ± 0.5 h, and sealed for use.The olefination reagent was cooled to -20-30 ° C, and 1.2 kg of a solution of Intermediate VIII in 20 L of dichloromethane was added dropwise. After the addition, the temperature was raised to 15-20 ° C and the reaction was stirred for 180 ± 10 min. TLC was used to detect the endpoint of the reaction. The reacted solution was pumped into a 200 L reaction vessel (30 L of dichloromethane, 100 L of purified water, 10 kg of sodium hydrogencarbonate mixed system) and stirred for 60-70 min. The mixture was washed with a stainless steel centrifuge, and the filter cake was washed twice with dichloromethane (16L). The combined filtrates were collected and separated, and the aqueous phase was extracted with dichloromethane (16L×2).Concentrate to dryness in vacuo at 25-30 ° C to give 6-benzyloxy-9-((1S,3R,3S)-4-benzyloxy-3-benzyloxymethyl-2-methylenecyclopentyl) -N-((4-methoxybenzene)The product is a yellow powder of diphenylmethyl)-9H-indol-2-amine, intermediate IX, a single step yield of 88percent and a purity of 93.6percent.

Reference： [1] Patent: CN108148061, 2018, A, . Location in patent: Paragraph 0028; 0029; 0030; 0031; 0032; 0033; 0034

2
[ 3587-60-8 ]
[ 142217-80-9 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 1997, vol. 7, # 2, p. 127 - 132
[2] Bioorganic and Medicinal Chemistry Letters, 1997, vol. 7, # 2, p. 127 - 132

3
[ 39939-07-6 ]
[ 142217-80-9 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 1997, vol. 7, # 2, p. 127 - 132
[2] Bioorganic and Medicinal Chemistry Letters, 1997, vol. 7, # 2, p. 127 - 132

4
[ 110567-22-1 ]
[ 142217-80-9 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 1997, vol. 7, # 2, p. 127 - 132
[2] Bioorganic and Medicinal Chemistry Letters, 1997, vol. 7, # 2, p. 127 - 132

5
[ 117641-39-1 ]
[ 142217-80-9 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 1997, vol. 7, # 2, p. 127 - 132
[2] Bioorganic and Medicinal Chemistry Letters, 1997, vol. 7, # 2, p. 127 - 132

6
[ 110567-21-0 ]
[ 142217-80-9 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 1997, vol. 7, # 2, p. 127 - 132
[2] Bioorganic and Medicinal Chemistry Letters, 1997, vol. 7, # 2, p. 127 - 132

7
[ 142217-78-5 ]
[ 142217-80-9 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 1997, vol. 7, # 2, p. 127 - 132
[2] Bioorganic and Medicinal Chemistry Letters, 1997, vol. 7, # 2, p. 127 - 132

8
[ 142217-77-4 ]
[ 142217-80-9 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 1997, vol. 7, # 2, p. 127 - 132
[2] Bioorganic and Medicinal Chemistry Letters, 1997, vol. 7, # 2, p. 127 - 132

9
[ 4984-82-1 ]
[ 142217-80-9 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 1997, vol. 7, # 2, p. 127 - 132
[2] Bioorganic and Medicinal Chemistry Letters, 1997, vol. 7, # 2, p. 127 - 132

10
[ 142217-79-6 ]
[ 74-95-3 ]
[ 142217-80-9 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 1997, vol. 7, # 2, p. 127 - 132

[ 142217-80-9 ] Synthesis Path-Downstream 1~17

1
[ 142217-80-9 ]
[ 142217-81-0 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In tetrahydrofuran; methanol; ethanol; chloroform;	J. [1S-(1alpha,3alpha,4beta)]-2-Amino-1,9-dihydro-9-[2-methylene-4-(phenylmethoxy)-3-[(phenyl-methoxy)methyl]cyclopentyl]-6H-purin-6-one A mixture of crude [1S-(1alpha,3alpha,4beta)]-N-[(4-methoxyphenyl)diphenylmethyl]-6-(phenylmethoxy)-9-[2-methylene-4-(phenylmethoxy)-3-[(phenylmethoxy)-methyl]cyclopentyl]-9H-purin-2-amine (2.5 g), tetrahydrofuran (25 ml), methanol (25 ml) and 3N hydrochloric acid (12.5 ml) was heated at 50 for 2.5 hours and cooled to room temperature. The pH was adjusted to 7.3 with 1N potassium hydroxide, and the mixture was extracted with ethyl acetate (3*120 ml). The ethyl acetate extract was dried (sodium sulfate) and concentrated in vacuo to a residue, which was applied to a column of Merck silica gel (340 ml) packed in 3% ethanol in chloroform. Elution with a gradient of 3-20% ethanol in chloroform gave 316 mg of desired product as a residue.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1997,vol. 7,p. 127 - 132
[2]Patent: US5206244,1993,A

2
[ 142217-79-6 ]
[ 74-95-3 ]
[ 142217-80-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1997,vol. 7,p. 127 - 132

3
[ 142217-79-6 ]
Nysted reagent [ No CAS ]
[ 142217-80-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1997,vol. 7,p. 127 - 132

4
[ 3587-60-8 ]
[ 142217-80-9 ]