[ CAS No. 91424-39-4 ] {[proInfo.proName]}

Name: 91424-39-4|Diethyl 3-(tert-Butyldimethylsilyloxy)glutarate|95%
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2D 3D

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Quality Control of [ 91424-39-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 91424-39-4 ]

SDS Specification

Alternatived Products of [ 91424-39-4 ]

Product Details of [ 91424-39-4 ]

CAS No. :	91424-39-4	MDL No. :	MFCD16251279
Formula :	C₁₅H₃₀O₅Si	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	PPZUZFQSSULNGN-UHFFFAOYSA-N
M.W :	318.48	Pubchem ID :	13327289
Synonyms :

Calculated chemistry of [ 91424-39-4 ]

Physicochemical Properties

Num. heavy atoms :	21
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.87
Num. rotatable bonds :	11
Num. H-bond acceptors :	5.0
Num. H-bond donors :	0.0
Molar Refractivity :	85.74
TPSA :	61.83 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.89 cm/s

Lipophilicity

Log Po/w (iLOGP) :	3.36
Log Po/w (XLOGP3) :	3.31
Log Po/w (WLOGP) :	3.28
Log Po/w (MLOGP) :	2.09
Log Po/w (SILICOS-IT) :	1.83
Consensus Log Po/w :	2.78

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	1.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.17
Solubility :	0.213 mg/ml ; 0.00067 mol/l
Class :	Soluble
Log S (Ali) :	-4.28
Solubility :	0.0165 mg/ml ; 0.0000519 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-3.51
Solubility :	0.0984 mg/ml ; 0.000309 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	4.19

Safety of [ 91424-39-4 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 91424-39-4 ]

* 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 [ 91424-39-4 ]
Downstream synthetic route of [ 91424-39-4 ]

[ 91424-39-4 ] Synthesis Path-Upstream 1~2

1
[ 91424-39-4 ]
[ 91424-40-7 ]

Yield	Reaction Conditions	Operation in experiment
68%	With sodium hydroxide; acetic anhydride In methanol; diethyl ether; benzene	B. 4-[[(Dimethylethyl)dimethylsilyl]oxy]dihydro-2H-pyran-2,6(3H)-dione A solution of Part A silyl-ether (theory 63.6 g, 200 mmole) in methanol (200 ml) was treated with NaOH pellets (16.0 g, 400 mmole) and stirred at room temperature under argon for 18 hours. The cloudy yellow solution was evaporated to dryness and dried in vacuo to give the diNa salt as a pale yellow solid. The diNa salt (42.1 g) was suspended in benzene (400 ml), treated with acetic anhydride (200 ml) and refluxed under argon for 1.5 hours. The brown mixture was concentrated in vacuo and the residue partitioned between ethyl acetate and half-saturated NaHCO₃ solution. The organic phase was washed with half saturated NaHCO₃ and saturated NaCl solutions, dried over Na₂ SO₄ and evaporated to give the crude title anhydride as a brown solid. The crude product was taken up in ethyl ether, treated with Darco (3 g), filtered through Celite and evaporated. The crystalline residue was triturated with cold hexane to give pure title anhydride (33.26 g, 68percent overall from diethyl 3-hydroxy glutarate) as white plates, m.p. 77°-78° C., C¹³ -NMR (15 MHz, CDCl₃)--5.22 ppm, 17.64, 25.31, 38.88, 61.87, 165.26.

Reference： [1] Patent: US4804770, 1989, A,
[2] Journal of Organic Chemistry, 1984, vol. 49, # 19, p. 3657 - 3659
[3] Journal of Organic Chemistry, 1988, vol. 53, # 10, p. 2374 - 2378
[4] Journal of Medicinal Chemistry, 1987, vol. 30, # 10, p. 1858 - 1873
[5] European Journal of Organic Chemistry, 2014, vol. 2014, # 3, p. 631 - 638
[6] Patent: CN107011378, 2017, A,

2
[ 91424-39-4 ]
[ 147118-35-2 ]

Reference： [1] Patent: CN107011378, 2017, A,

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Related Functional Groups of
[ 91424-39-4 ]

Organosilicon

[ 91424-40-7 ]

3-(tert-Butyldimethylsilyloxy)glutaric anhydride

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Yield	Reaction Conditions	Operation in experiment
	In dichloromethane;	1-J. 3-(t-Butyldimethylsilyloxy)glutaric acid, diethyl ester To a solution of imidazole (40.85 g, 600 mmol) in dry methylene chloride (300 ml) was added dropwise a solution of t-butyldimethylsilyl chloride (45.2 g, 300 mmol) in dry methylene chloride (100 ml). After 15 minutes, the solution was treated dropwise over a 40-minute period with a solution of diethyl 3-hydroxyglutarate (40.8 g, 200 mmol) in methylene chloride (100 ml). After stirring at room temperature under argon for 18 hours, the mixture was washed with water and saturated sodium chloride solution, dried over sodium sulfate and evaporated. The crude product (73.04 g) was purified by chromatography on Merck silica gel (4000 ml), eluding with ether-hexane (1:9) to give intermediate compound 1-J (about 65 g, theory 63.6 g) as a colorless oil. Thin layer chromatography: (ethyl acetate-hexane 1:1) Rf-0.46 (Rf of 3-hydroxyglutarate was 0.20). C13 -NMR (15 MHz, CDCl3) -5.02 ppm, 14.00, 17.77, 25.50, 42.51, 60.24, 66.28, 170.78.
	In dichloromethane;	A. 3-[[(1,1-Dimethylethyl)dimethylsilyl]-oxy]pentanedioic acid, diethyl ester [Ref.: JOC 49, 3657 (1984)] To a solution of imidazole (40.85 g, 600 mmole) in dry CH2 Cl2 (300 ml) was added dropwise a solution of t-butyldimethylsilyl chloride (45.2 g, 300 mmole) in dry CH2 Cl2 (100 ml). After 15 minutes, the solution was treated dropwise over a 40 minute period with a solution of diethyl 3-hydroxyglutarate (40.8 g, 200 mmole) in CH2 Cl2 (100 ml). After stirring at room temperature under argon for 18 hours, the mixture was washed with water and saturated NaCl solution, dried over Na2 SO4 and evaporated. The crude product (73.04 g) was purified by chromatography on Merck silica gel (4000 ml), eluding with ethyl ether-hexane (1:9) to give title compound (~65 g, theory 63.6) as a colorless oil. TLC: (ethyl acetate-hexane; 1:1) Rf =0.46 (Rf of title compound=0.20). C13 -NMR (15 MHz, CDCl3)--5.02 ppm, 14.00, 17.77, 25.50, 42.51, 60.24, 66.28, 170.78.

Yield	Reaction Conditions	Operation in experiment
93%	With sodium hydroxide; In methanol; at 20 - 30℃;	(2) Into a 200 mL three-necked flask, 80 g of methanol was charged,12 g (0.3 mol) NaOH,1.8g water,Stirring to dissolve,Drop to room temperature,Add J0-2 oil (0.1mol) and16g anhydrous methanol solution,Keep the temperature 20-30 ,TLC tracking, the reaction was complete;Frozen brine cooling, stirring below 10 2h;Filtration, wash the filter cake with anhydrous methanol to give a pale yellow powdery solid,Drying, get J0-3 about 28g, the total yield of 93%;
68 g	With sodium hydroxide; In ethanol; at 2℃; for 5h;Reflux;	In a round-bottomed flask, 60 g (0.217 mol) of 3-tert-butyldimethylsilyl glutarate was added, and the temperature was lowered to 2 C. 213.5 g of absolute ethanol and 49.3 g of sodium hydroxide were added, and dissolved by stirring; removed In a cold water bath, the resulting suspension was refluxed for 5 h. The solvent was evaporated to dryness on a rotary evaporator under high vacuum to obtain 68 g of an off-white solid.That is, the crude product of 3-tert-butyldimethylsilyl glutarate (VI).

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 91424-39-4 ] {[proInfo.proName]}

Quality Control of [ 91424-39-4 ]

Related Doc. of [ 91424-39-4 ]

Product Details of [ 91424-39-4 ]

Calculated chemistry of [ 91424-39-4 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 91424-39-4 ]

Application In Synthesis of [ 91424-39-4 ]

[ 91424-39-4 ] Synthesis Path-Upstream 1~2

[ 91424-39-4 ] Synthesis Path-Downstream 1~40

Related Functional Groups of [ 91424-39-4 ]

Organosilicon

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[ 91424-39-4 ]