Home Cart Sign in  
Chemical Structure| 31618-90-3 Chemical Structure| 31618-90-3
Chemical Structure| 31618-90-3

(Diethoxyphosphoryl)methyl 4-methylbenzenesulfonate

CAS No.: 31618-90-3

4.5 *For Research Use Only !

Cat. No.: A351651 Purity: 98%

Change View

Size Price

US Stock

Global Stock

In Stock
5g łÇʶÊÊ Inquiry Inquiry
10g łÇͶÊÊ Inquiry Inquiry
25g łÇó¶ÊÊ Inquiry Inquiry
100g ł§î¶ÊÊ Inquiry Inquiry
500g łòò¶ÊÊ Inquiry Inquiry
1kg łÇÇʶÊÊ Inquiry Inquiry

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 5g

    łÇʶÊÊ

  • 10g

    łÇͶÊÊ

  • 25g

    łÇó¶ÊÊ

  • 100g

    ł§î¶ÊÊ

  • 500g

    łòò¶ÊÊ

  • 1kg

    łÇÇʶÊÊ

In Stock

- +

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support Online Technical Q&A
Product Citations

Alternative Products

Product Details of [ 31618-90-3 ]

CAS No. :31618-90-3
Formula : C12H19O6PS
M.W : 322.31
SMILES Code : O=S(C1=CC=C(C)C=C1)(OCP(OCC)(OCC)=O)=O
MDL No. :MFCD03412078
InChI Key :UOEFFQWLRUBDME-UHFFFAOYSA-N
Pubchem ID :4193599

Safety of [ 31618-90-3 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H332-H335
Precautionary Statements:P261-P280-P305+P351+P338

Calculated chemistry of [ 31618-90-3 ] Show Less

Physicochemical Properties

Num. heavy atoms 20
Num. arom. heavy atoms 6
Fraction Csp3 0.5
Num. rotatable bonds 8
Num. H-bond acceptors 6.0
Num. H-bond donors 0.0
Molar Refractivity 75.65
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

97.09 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

2.56
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

1.65
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

4.0
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

1.61
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

0.96
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.16

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-2.57
Solubility 0.864 mg/ml ; 0.00268 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-3.3
Solubility 0.161 mg/ml ; 0.000499 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-3.92
Solubility 0.0391 mg/ml ; 0.000121 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

No
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

Yes
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

Yes
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-7.09 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

0.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

2.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

3.61

Application In Synthesis [ 31618-90-3 ]

* 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.

  • Downstream synthetic route of [ 31618-90-3 ]

[ 31618-90-3 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 23377-40-4 ]
  • [ 31618-90-3 ]
  • P-[[[(4-methylphenyl)sulfonyl]oxy]methyl]mono[3-(hexadecyloxy)propyl]ester sodium [ No CAS ]
  • 2
  • [ 31618-90-3 ]
  • [ 428855-17-8 ]
  • diethyl ({1-[(dibenzylamino)methyl]cyclopropoxy}methyl)phosphonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
87.5% With lithium tert-butoxide; In tetrahydrofuran; at 60℃;Inert atmosphere; Under nitrogen protection,A solution of 1- (dibenzylamino) methylcyclopropanol (II-1) (1.15 g, 4.3 mmol) in tetrahydrofuran (10 ml)Lithium tert-butoxide (0.5 g, 6.2 mmol) and diethyl p-toluenesulfonyloxymethylphosphonate (III-1) (2.0 g, 6.2 mmol)The temperature was raised to 60 C.TLC monitoring reaction end,After cooling to room temperature, add saturated ammonium chloride solution (10ml)Solid precipitation.filter,The filter cake was washed with ethyl acetate (10 ml x 2)The combined organic layers were dried over anhydrous sodium sulfate,filter,Concentrated crude,Purification by flash column chromatography (petroleum ether: ethyl acetate = 2: 1)Get the oil,A total of 1.57g,The yield was 87.5%;
  • 3
  • [ 24630-67-9 ]
  • [ 98-59-9 ]
  • [ 31618-90-3 ]
YieldReaction ConditionsOperation in experiment
86.5% With sodium hydroxide; In dichloromethane; at 5 - 10℃; for 3h; (2) 100 ml of dichloromethane and 78.7 g of p-toluenesulfonyl chloride were added to the above reaction solution.Cool down to 5 C, add 30% of liquid alkali 63.8 grams, the reaction is exothermic,Keep the dropping temperature between 5-10 C, and add 1 hour.After the addition is completed, the temperature is kept at 10 C for 2 hours, and the sample is tested.The reaction of 0.15% (less than 0.2%) of p-toluenesulfonyl chloride is completed.Still, layer, the aqueous layer was extracted once with 50 ml of dichloromethane.Combine the layers and add 100 ml of water to wash once.The water layer is separated; the layer is firstly distilled to recover dichloromethane.The residual dichloromethane was then dried under reduced pressure.Residue 115.1 g of diethyl p-toluenesulfonyloxymethylphosphonate,99.3% purity,The molar yield (calculated as p-toluenesulfonyl chloride) was 86.5%.
  • 4
  • [ 31618-90-3 ]
  • [ 14047-28-0 ]
  • [ 147127-19-3 ]
YieldReaction ConditionsOperation in experiment
88% Under nitrogen protection, 1.25 kg of compound XIV,6.0 kg of DMF and 0.73 kg of magnesium isopropoxide.The temperature was raised to 65 C, and the reaction was stirred for 1 hour.The temperature was lowered to 45-55 C, and DEMP (Formula VI) was slowly added dropwise to the reactor in batches.After the addition was completed, the mixture was stirred at 45 to 55 C for 10 hours.The reaction was determined to be complete by HPLC, and DMF and isopropanol were concentrated under reduced pressure.6.25 kg of concentrated hydrochloric acid was added to the concentrate, the temperature was raised to 90 C, and the reaction was stirred for 10 hours.After the reaction was completed, the temperature was lowered to 10-15 C and stirred for 20-30 minutes.After filtration, the filter cake was washed with 1.0 kg of a dilute hydrochloric acid solution, and the filter cake was discarded.The filtrate was transferred to a reaction kettle, 2.0 kg of dichloromethane was added, and stirred for 15 minutes.Let stand for 30 minutes.The layers were separated, the aqueous phase was collected, and the hydrochloric acid was concentrated under reduced pressure.7.5 kg of water was added to the concentrate, the temperature was raised to 40 C, and the mixture was stirred until dissolved.Slowly add 40% NaOH aqueous solution to adjust the pH to 3.0.After the dropwise addition was completed, the mixture was stirred at 50 C for 3 hours.Cool naturally to room temperature and stir for 10-12 hours.Filter, filter cake was washed with 0.8kg of water,Get tenofovir crude.Purity 96.7%, containing 0.78% condensation impurities, genotoxic impurities 160ppm,The S-isomer impurity was 0.58%, and the isomer was 1.83%.
 

Historical Records

Technical Information

Categories