[ CAS No. 54325-28-9 ] {[proInfo.proName]}

Name: 54325-28-9|(2S,3R,4S,5S,6R)-6-((Trityloxy)methyl)tetrahydro-2H-pyran-2,3,4,5-tetraol|95%
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SKU: A476635
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2D 3D

Structure of 54325-28-9 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 54325-28-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 54325-28-9 ]

SDS Specification

Alternatived Products of [ 54325-28-9 ]

Product Details of [ 54325-28-9 ]

CAS No. :	54325-28-9	MDL No. :	MFCD00061632
Formula :	C₂₅H₂₆O₆	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	WMNZCEKHTHLIRQ-SJSRKZJXSA-N
M.W :	422.47	Pubchem ID :	54438697
Synonyms :

Calculated chemistry of [ 54325-28-9 ]

Physicochemical Properties

Num. heavy atoms :	31
Num. arom. heavy atoms :	18
Fraction Csp3 :	0.28
Num. rotatable bonds :	6
Num. H-bond acceptors :	6.0
Num. H-bond donors :	4.0
Molar Refractivity :	113.81
TPSA :	99.38 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.41 cm/s

Lipophilicity

Log Po/w (iLOGP) :	3.63
Log Po/w (XLOGP3) :	2.07
Log Po/w (WLOGP) :	1.69
Log Po/w (MLOGP) :	1.34
Log Po/w (SILICOS-IT) :	2.21
Consensus Log Po/w :	2.19

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.8
Solubility :	0.0674 mg/ml ; 0.00016 mol/l
Class :	Soluble
Log S (Ali) :	-3.79
Solubility :	0.0691 mg/ml ; 0.000164 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-5.2
Solubility :	0.00265 mg/ml ; 0.00000627 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	4.88

Safety of [ 54325-28-9 ]

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 [ 54325-28-9 ]

* 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 [ 54325-28-9 ]
Downstream synthetic route of [ 54325-28-9 ]

[ 54325-28-9 ] Synthesis Path-Upstream 1~3

1
[ 50-99-7 ]
[ 76-83-5 ]
[ 54325-28-9 ]

Yield	Reaction Conditions	Operation in experiment
88%	at 80℃; for 4 h;	To glucose (5g; 0.0277 mole) as a suspension in pyridine (50 mL) was added trityl chloride and stirred at 8O⁰C for about 4 hours. The completion of the reaction was checked by TLC using dichloromethane: methanol (85:15). The reaction was quenched with water (100 mL) and extracted with dichloromethane (150 ml x 2). The organic layer was washed with saturated solution of sodium bicarbonate and water, dried over anhydrous sodium sulfate and the solvent was removed by rotory evaporator. Trityl Chloride and pyridine were removed by triturating with hexane: diethyl ether mixture (10OmL) to afford the desired product (10.3 g; 88percent), LC-MS gave the M⁺ at 446 amu in accordance with the structure.

Reference： [1] Patent: WO2007/54977, 2007, A2, . Location in patent: Page/Page column 21
[2] Patent: KR101595939, 2016, B1, . Location in patent: Paragraph 0102-0103

2
[ 2280-44-6 ]
[ 76-83-5 ]
[ 54325-28-9 ]

Reference： [1] Tetrahedron, 2007, vol. 63, # 40, p. 10042 - 10053
[2] Tetrahedron Letters, 1989, vol. 30, # 1, p. 35 - 38
[3] Carbohydrate Research, 1995, vol. 279, p. 281 - 291
[4] Tetrahedron Letters, 1996, vol. 37, # 23, p. 4015 - 4018
[5] Chemical and Pharmaceutical Bulletin, 1997, vol. 45, # 4, p. 626 - 630
[6] Carbohydrate Research, 1997, vol. 303, # 1, p. 1 - 15
[7] Carbohydrate Research, 1997, vol. 301, # 3-4, p. 123 - 143
[8] Journal of the American Chemical Society, 1999, vol. 121, # 51, p. 12196 - 12197
[9] Organic Letters, 2009, vol. 11, # 4, p. 939 - 942
[10] Journal of Medicinal Chemistry, 2011, vol. 54, # 5, p. 1481 - 1489
[11] Molecules, 2013, vol. 18, # 9, p. 11198 - 11218
[12] Journal of Labelled Compounds and Radiopharmaceuticals, 2014, vol. 57, # 14, p. 737 - 743
[13] Organic and Biomolecular Chemistry, 2017, vol. 15, # 23, p. 5025 - 5032
[14] Patent: CN107286207, 2017, A, . Location in patent: Paragraph 0017

3
[ 492-62-6 ]
[ 76-83-5 ]
[ 54325-28-9 ]

Reference： [1] Patent: WO2006/115312, 2006, A1, . Location in patent: Page/Page column 20
[2] Patent: US2008/39421, 2008, A1, . Location in patent: Page/Page column 4; 8

[ 54325-28-9 ] Synthesis Path-Downstream 1~2

1
[ 1779-58-4 ]
[ 54325-28-9 ]
(3aR,5R,6S,6aR)-6-Hydroxy-5-((R)-1-hydroxy-2-trityloxy-ethyl)-tetrahydro-furo[3,2-b]furan-2-one [ No CAS ]
(E)-(4S,5R,6R,7R)-4,5,6,7-Tetrahydroxy-8-trityloxy-oct-2-enoic acid methyl ester [ No CAS ]

Reference： [1]Tetrahedron Letters,1995,vol. 36,p. 6467 - 6470

2
[ 10257-28-0 ]
[ 76-83-5 ]
[ 54325-28-9 ]

Yield	Reaction Conditions	Operation in experiment
100%	With pyridine at 50℃; for 48h; Inert atmosphere;	4.2. 3,4-O-Isopropylidene-6-O-triphenylmethyl-d-galactopyranoside (8) Trityl chloride (16.4 g, 58.8 mmol) was added to a solution of d-galactose (7) (10 g, 55.5 mmol) in pyridine (150 mL). The reaction mixture was stirred at 50 °C for 48 h and concentrated in vacuo. The resulting residue was purified by chromatography through a short silica column and the tritylated galactose was eluted with acetone and crystallised from EtOH to afford the tritylated galactose (23.4 g, 55.4 mmol, quant.) [Rf: 0.17 (EtOAc)] as a white powder.
47%	With 1,4-diaza-bicyclo[2.2.2]octane for 15h;
	With triethylamine In N,N-dimethyl-formamide Ambient temperature;

	With pyridine Ambient temperature;
	With pyridine at 50℃; for 32h;
	In pyridine at 50℃; for 6h;
	With pyridine at 80℃; for 1.5h; regioselective reaction;
	With pyridine at 90℃; for 16h; regioselective reaction;	1,2,3,4-Tetra-O-benzoyl-α-D-galactopyranuronic acid, allyl ester (20a). D-Galactose (5.4 g, 0.03 mol) and trityl chloride (17.0 g, 0.04 mol) were dried under diminished pressure for 3 h. The mixture was taken up in pyridine (80 mL) and heated at 90 °C for 16 h, then The solution was then cooled to 0 °C and benzoyl chloride (17 mL, 0.15 mol) was added slowly and he reaction mixture was then allowed to attain room temp, stirred for 20 h, and the mixture was then diluted with CH2Cl2 and washed with water, 2 M HCl, satd aq NaHCO3, brine, dried over Na2SO4 and the solvent was removed under diminished pressure. The resulting syrup was dissolved in CH2Cl2-MeOH (1:2, 150 mL) and conc. H2SO4 (15 mL) was added. The mixture was stirred for 1 h at room temp and then washed with water, satd aq NaHCO3, brine, and dried over Na2SO4, and the solvent was removed under diminished pressure. Flash chromatography (petroleum ether-EtOAc, 4:1) gave 19a as a white solid and a mixture of anomers (10.9 g, 61%). The NMR data (1H and 13C) for 19a were in agreement with data reported in the literature [36]. To 19a (10.0 g, 0.017 mol) in CH2Cl2 (100 mL) and H2O (40 mL) were added TEMPO (0.5 g) and BAIB (16.2 g, 0.05 mol). The mixture was stirred vigorously for 2 h and satd Na2S2O3(40 mL) was then added and the resulting mixture stirred for 15 min. The layers were separated and the aq phase acidified with 1M HCl and extracted with CH2Cl2 (×3). The combined organic layers weredried over Na2SO4, and the solvent was removed under diminished pressure to give the galacturonic acid intermediate (9.5 g, 91%). The resulting solid was dissolved in THF (100 mL), to this K2CO3 (115 mg,0.84 mmol), 18-crown-6 (10 mg) and allyl iodide (140 mg, 0.84 mmol, 80 μL) were added. The reaction was stirred in the dark for 16 h at room temp. The reaction mixture was diluted with Et2O,washed with water, sodium thiosulfate, water, brine, dried over MgSO4. The solvent was then removed under reduced pressure and then flash chromatography (EtOAc-cyclohexane 1:4) of the residue gave 20a (484 mg, 44%) as a white solid;
	With pyridine at 50℃; for 48h; Inert atmosphere;	To a suspension of D-galactose 2 (4.85 g, 26.9 mmol) in pyridine (49 mL)was added trityl chloride (5.00 g, 17.9 mmol). The mixture was then warmedup to 50C and stirred for 48 h under argon atmosphere at 50C. The reactionmixture was then concentrated in vacuo and the residue was dissolved in1-butanol. The solution was washed with water (ca. 100 mL × 2), brine (ca.100 mL), dried over Na2SO4, and concentrated in vacuo to give crude 6-Otrityl-D-galactose (3) and used for the next step without further purification(see Fig. S1 for the 1H NMR of the crude material).

Reference： [1]Location in patent: experimental part Cheng, Janice M.H.; Chee, Stephanie H.; Knight, Deborah A.; Acha-Orbea, Hans; Hermans, Ian F.; Timmer, Mattie S.M.; Stocker, Bridget L. [Carbohydrate Research, 2011, vol. 346, # 7, p. 914 - 926]
[2]Patil, Premanand Ramrao; Kartha, K.P. Ravindranathan [Journal of Carbohydrate Chemistry, 2008, vol. 27, # 5, p. 279 - 293]
[3]MacManus; Vulfson [Carbohydrate Research, 1995, vol. 279, p. 281 - 291]
[4]Lievre, Catherine; Frechou, Catherine; Demailly, Gilles [Carbohydrate Research, 1997, vol. 303, # 1, p. 1 - 15]
[5]Ning, Jun; Yi, Yuetao; Yao, Zhe [Synlett, 2003, # 14, p. 2208 - 2212]
[6]Li, Aixiao; Zeng, Ying; Kong, Fanzuo [Carbohydrate Research, 2004, vol. 339, # 3, p. 673 - 682]
[7]Lopez, Marie; Trajkovic, Jonathan; Bornaghi, Laurent F.; Innocenti, Alessio; Vullo, Daniela; Supuran, Claudiu T.; Poulsen, Sally-Ann [Journal of Medicinal Chemistry, 2011, vol. 54, # 5, p. 1481 - 1489]
[8]Pilgrim, Wayne; O'Reilly, Ciaran; Murphy, Paul V. [Molecules, 2013, vol. 18, # 9, p. 11198 - 11218]
[9]Orii, Ryo; Izumi, Masayuki; Kajihara, Yasuhiro; Okamoto, Ryo [Journal of Carbohydrate Chemistry, 2015, vol. 34, p. 560 - 566]

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P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
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P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
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P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
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P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
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P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
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H301	Toxic if swallowed
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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. 54325-28-9 ] {[proInfo.proName]}

Quality Control of [ 54325-28-9 ]

Related Doc. of [ 54325-28-9 ]

Product Details of [ 54325-28-9 ]

Calculated chemistry of [ 54325-28-9 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 54325-28-9 ]

Application In Synthesis of [ 54325-28-9 ]

[ 54325-28-9 ] Synthesis Path-Upstream 1~3

[ 54325-28-9 ] Synthesis Path-Downstream 1~2

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

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