[ CAS No. 3150-20-7 ] {[proInfo.proName]}

Name: 3150-20-7|(2R,3R,4S,5R,6S)-2-(Hydroxymethyl)-6-(4-methoxyphenoxy)tetrahydro-2H-pyran-3,4,5-triol|98%
Brand: Ambeed
SKU: A255771
Rating: 90 (28 reviews)

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Cat. No.: {[proInfo.prAm]}

2D 3D

Structure of 3150-20-7 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 3150-20-7 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 3150-20-7 ]

SDS Specification

Alternatived Products of [ 3150-20-7 ]

Product Details of [ 3150-20-7 ]

CAS No. :	3150-20-7	MDL No. :	MFCD06797126
Formula :	C₁₃H₁₈O₇	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	SIXFVXJMCGPTRB-KSSYENDESA-N
M.W :	286.28	Pubchem ID :	11300643
Synonyms :

Calculated chemistry of [ 3150-20-7 ]

Physicochemical Properties

Num. heavy atoms :	20
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.54
Num. rotatable bonds :	4
Num. H-bond acceptors :	7.0
Num. H-bond donors :	4.0
Molar Refractivity :	67.08
TPSA :	108.61 Å²

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) :	-8.56 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.66
Log Po/w (XLOGP3) :	-0.73
Log Po/w (WLOGP) :	-1.13
Log Po/w (MLOGP) :	-1.21
Log Po/w (SILICOS-IT) :	-0.7
Consensus Log Po/w :	-0.42

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.11
Solubility :	22.1 mg/ml ; 0.0771 mol/l
Class :	Very soluble
Log S (Ali) :	-1.07
Solubility :	24.1 mg/ml ; 0.0842 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.34
Solubility :	130.0 mg/ml ; 0.455 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	4.28

Safety of [ 3150-20-7 ]

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

Application In Synthesis of [ 3150-20-7 ]

* 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 [ 3150-20-7 ]

[ 3150-20-7 ] Synthesis Path-Downstream 1~88

1
[ 2872-65-3 ]
[ 3150-20-7 ]

Yield	Reaction Conditions	Operation in experiment
94%	With methanol; sodium methylate; at 20℃;	2. Synthesis of 1-O-(p-Methoxy phenyl)-beta-D-glucopyranoside; II (RSCL-0369) To a stirred solution of compound I (12 g, 24.2 mmol) in methanol (25 mL) was gradually added 2 mL of a 25% (w/v) sodium methoxide/methanol solution. The resulting solution was stirred at room temperature overnight. The mixture was neutralized by Amberlyst 15 ion-exchange (H+) resin. The neutralized reaction mixture was filtered, concentrated and purified using silica gel column chromatography (20% methanol/dichloromethane). The organic fractions containing desired product were concentrated and dried under high vacuum (2 mm/Hg) to provide viscous compound II (yield 6.5 g, 94%); Rf 0.55 (10% methanol/dichloromethane); 1H NMR (CD3OD) delta 3.77 (s, 3H), 4.06 (dd, 1H, J=12 Hz), 4.27 (dd, 1H, J=5.1 Hz), 4.52 (d, 1H, J=7.2 Hz), 6.81 (d, 1H), 6.94 (2d, 1H); MS m/z 309 (M+Na)+. Anal. Calculated for C13H18O7: C, 54.54; H, 6.34; O, 39.12. Found: C, 54.44; H, 6.42; O, 39.14. (Slaghek T M, et al. Carbohydr Res. 1994; 255:61-85.)
87%	With sodium methylate; In methanol; for 2h;	Step 2: (2R, 3S, 4S, 5R, 6S) -2- (hydroxymethyl) -6- (4-methoxyphenoxy) tetrahydro-2H-pyran-3, 4, 5-triol (19b) To a solution of 19a (20.0 g, 44 mmol) in MeOH (200 mL) was added a solution of NaOMe in MeOH (1M, 17.6 mL, 17.6 mmol) . The reaction mixture was stirred for 2 h, then neutralised by addition of Dowex 50wx8 (100-200, H+) . The mixture was filtered and concentrated to give a residue, which was washed with EtOAc (30 mL) to afford 19b as a white solid (10.9 g, 87) LC-MS (ESI) : 309.36 [M+Na]+.
	With methanol; sodium methylate; at 20℃; under 760.051 Torr; for 3h;	Compound 33: To a solution of 32 in dry MeOH was added catalytic amount of sodium methoxide (NaOMe) and stirred for 3 h at ambient temperature. The reaction was neutralized by adding Amberlite IR-120 and filtered, the resulting solution was concentrated to dryness to give 33 as white solid, which was directly used for next reaction without further purification.

	With methanol; sodium methylate; at 20℃; for 3h;	To a solution of 32 in dry MeOH was added catalytic amount of sodium methoxide (NaOMe) and stirred for 3 h at ambient temperature. The reaction was neutralized by adding Amberlite IR-120 and filtered, the resulting solution was concentrated to dryness to give 33 as white solid, which was directly used for next reaction without further purification
50 mg	With sodium methylate; In methanol; at 20℃; for 1h;Inert atmosphere;	General procedure: To a solution 2 and the acceptor ArOH (3.0 equiv) in dry DCM (0.1 M) was added afreshly prepared solution of BF3?OEt2 (1.0 equiv., 1M in dry DCM). The solution wasstirred 1 h and followed by TLC (30:70; EtOAc : hexanes). A solution of NaHCO3(aq) wasadded and the mixture was extracted with DCM, washed with brine, dried over Na2SO4,filtered and concentrated in vacuo. The alpha/beta ratio was measured by 1H NMR on the crude.The residue was treated with a freshly prepared solution MeONa (0.25 equiv., 0.5 M inmethanol) in dry methanol (0.3 M). The solution was stirred at r.t. for 1 h andneutralized with Amberlite IR-120 H+, filtered and concentrated in vacuo to give a whitesolid. Quick flash column chromatography (10:90; MeOH:DCM) removed excess of ArOHand led to the beta-D anomer, which was recrystallized in hot ethanol. 4-Methoxyphenyl-alpha-D-glucopyranoside (24)White solid (50 mg, 82%, 1:>20, alpha:beta).Melting point : 170C (lit. 175-177C)3[alpha]D25 -58.9 (c 0.05, MeOH)IR (neat) numax 3358, 3026, 2921, 1645, 1508, 1219, 1072 cm-11H NMR (500 MHz, CD3OD): delta = 7.05 (d, J = 9.1 Hz, 2H), 6.83 (d, J = 9.1 Hz, 2H), 4.77 (d, J= 7.5 Hz, 1H, H-1), 3.88 (dd, J = 8.8, 3.4 Hz, 1H, H-4), 3.75 (s, 3H), 3.72 - 3.65 (m, 1H, H-3), 3.48 - 3.36 (m, 4H, H-2, H-5, 2H-6).13C NMR (125 MHz, CD3OD): delta = 156.7, 153.2, 119.2, 115.4, 103.5, 78.1, 78.0, 75.0, 71.4,62.6, 56.0.HRMS: m/z [ESI] calcd for C13H18O7Na (M+Na)+ : 309.0945, found: 309.0954 (+3.03ppm).

Reference： [1]Australian Journal of Chemistry,2009,vol. 62,p. 575 - 584
[2]Carbohydrate Research,1996,vol. 295,p. 41 - 55
[3]Patent: US2009/215710,2009,A1 .Location in patent: Page/Page column 19
[4]Patent: WO2016/41470,2016,A1 .Location in patent: Paragraph 0159; 0161
[5]Patent: US6339162,2002,B1 .Location in patent: Example 9
[6]Planta Medica,2005,vol. 71,p. 147 - 152
[7]Chemische Berichte,1933,vol. 66,p. 378,383
[8]Carbohydrate Research,1994,vol. 255,p. 61 - 85
[9]Carbohydrate Research,1998,vol. 309,p. 175 - 188
[10]Journal of Organic Chemistry,2000,vol. 65,p. 3064 - 3073
[11]Tetrahedron,2008,vol. 64,p. 92 - 102
[12]Organic and Biomolecular Chemistry,2013,vol. 11,p. 4971 - 4974
[13]Journal of Organic Chemistry,2013,vol. 78,p. 8004 - 8019
[14]European Journal of Organic Chemistry,2014,vol. 2014,p. 4624 - 4642
[15]Patent: US2015/71960,2015,A1 .Location in patent: Paragraph 0288; 0291; 0292; 0314
[16]Patent: US2016/102116,2016,A1 .Location in patent: Paragraph 0269
[17]Synthesis,2016,vol. 48,p. 3575 - 3588

2
[ 124-41-4 ]
C₃₃H₃₈O₁₅ [ No CAS ]
[ 1916-07-0 ]
[ 3150-20-7 ]

Reference： [1]Phytochemistry,1987,vol. 26,p. 515 - 518

3
[ 69304-37-6 ]
[ 3150-20-7 ]
[ 155194-81-3 ]
p-Methoxyphenyl 2,3:4,6-bis-O-(1,1,3,3-tetraisopropyl-1,3-disiloxane-1,3-diyl)-β-D-glucopyranoside [ No CAS ]

Reference： [1]Journal of Carbohydrate Chemistry,1994,vol. 13,p. 81 - 110

4
[ 1125-88-8 ]
[ 3150-20-7 ]
[ 144367-31-7 ]

Yield	Reaction Conditions	Operation in experiment
85%	With toluene-4-sulfonic acid; In N,N-dimethyl-formamide; at 20℃; for 16h;	3. Synthesis of 1-O-(p-Methoxy phenyl)-4,6-O-benzylidene-beta-D-glucopyranoside; III (RSCL-0370) To Compound II (3.5 g, 12.23 mmol) in anhydrous N,N-dimethylformamide (35 mL) was added dropwise benzaldehyde dimethyl acetal (3.02 mL, 20.17 mmol) followed by addition of p-toluene sulphonic acid (0.2 g). The reaction was stirred at room temperature for 16 h. N,N-Dimethylformamide was removed under high vacuum and the residue was purified using silica gel column (10% methanol/dichloromethane). The organic fractions containing desired product were concentrated and dried under high vacuum (2 mm/Hg) to provide viscous compound III (yield 2.9 g, 85%); Rf 0.45 (15% acetone/dichloromethane); 1H NMR (CDCl3) delta 3.79 (s, 3H), 4.90 (d, 1H, J=7.7 Hz), 5.58 (s, 1H), 6.81 (d, 1H), 6.94 (2d, 1H), 7.36-7.37 (m, 2H), 7.48-7.52 (m, 3H); MS m/z 397 (M+Na)+. Anal. Calculated for C20H22O7: C, 64.16; H, 5.92; O, 29.91. Found: C, 64.08; H, 5.90; O, 30.02 (Slaghek T M, et al. Carbohydr Res. 1994; 255:61-85.)

Reference： [1]Patent: US2009/215710,2009,A1 .Location in patent: Page/Page column 19
[2]Carbohydrate Research,1994,vol. 255,p. 61 - 85
[3]Journal of Organic Chemistry,2000,vol. 65,p. 3064 - 3073

5
[ 3150-20-7 ]
[ 29368-59-0 ]

Reference： [1]Journal of general chemistry of the USSR,1986,vol. 56,p. 2339 - 2343
Zhurnal Obshchei Khimii,1986,vol. 56,p. 2642 - 2647

6
[ 3150-20-7 ]
[ 2280-44-6 ]
[ 150-76-5 ]

Reference： [1]Carbohydrate Research,1982,vol. 100,p. 221 - 234

7
[ 77-76-9 ]
[ 3150-20-7 ]
[ 180274-49-1 ]
(3aR,4S,5aR,9aR,9bS)-4-(4-Methoxy-phenoxy)-2,2,8,8-tetramethyl-hexahydro-[1,3]dioxolo[4',5':4,5]pyrano[3,2-d][1,3]dioxine [ No CAS ]

Reference： [1]Liebigs Annales,1996,p. 1239 - 1257

8
[ 100-39-0 ]
[ 3150-20-7 ]
[ 67525-68-2 ]

Reference： [1]Carbohydrate Research,1996,vol. 295,p. 41 - 55

9
[ 2106-10-7 ]
[ 3150-20-7 ]
C₃₁H₄₈O₂₂ [ No CAS ]
4-methoxyphenyl (β-D-glucopyranosyl)-(1->4)-β-D-glucopyranoside [ No CAS ]
(2S,3R,4S,5S,6R)-2-{(2R,3S,4R,5R,6S)-6-[(2R,3S,4R,5R,6S)-4,5-Dihydroxy-2-hydroxymethyl-6-(4-methoxy-phenoxy)-tetrahydro-pyran-3-yloxy]-4,5-dihydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy}-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1998,vol. 120,p. 5583 - 5584

10
[ 2106-10-7 ]
[ 3150-20-7 ]
4-methoxyphenyl (β-D-glucopyranosyl)-(1->4)-β-D-glucopyranoside [ No CAS ]
(2S,3R,4S,5S,6R)-2-{(2R,3S,4R,5R,6S)-6-[(2R,3S,4R,5R,6S)-4,5-Dihydroxy-2-hydroxymethyl-6-(4-methoxy-phenoxy)-tetrahydro-pyran-3-yloxy]-4,5-dihydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy}-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1998,vol. 120,p. 5583 - 5584

11
[ 18162-48-6 ]
[ 3150-20-7 ]
(2R,3S,4S,5R,6S)-2-(((tert-butyldimethylsilyl)oxy)methyl)-6-(4-methoxyphenoxy)tetrahydro-2H-pyran-3,4,5-triol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With 1H-imidazole; In N,N-dimethyl-formamide; at 0 - 20℃; for 12h;Inert atmosphere;	Step 1: (2R, 3S, 4S, 5R, 6S) -2- ( ( (tert-Butyldimethylsilyl) oxy) methyl) -6- (4-methoxyphenoxy) tetrahydro-2H-pyran-3, 4, 5-triol (5a) To a solution of compound 19b (3.74 g, 13.1 mmol) , imidazole (1.96 g, 28.8 mmol) in DMF (30 mL) was added a solution of TBSCl (2.37 g, 15.7 mmol) in DMF (5 mL) dropwise at 0under a nitrogen atmosphere. After stirring at room temperature for 12 hrs, the reaction mixture was poured into water (100 mL) and extracted with EtOAc (2×30 mL) . The organic layer was evaporated and the crude product was purified by column chromatography (200300 mesh silica gel, eluted with EtOAc/PE 1:1) to afford compound 5a as a white solid (3.85 g, 74) :1H NMR (400 MHz, DMSO-d6) delta 6.98 (d, J 8.8 Hz, 2H) , 6.80 (d, J 8.8 Hz, 2H) , 5.30 (d, J 5.2 Hz, 1H) , 5.11 (d, J 4.8 Hz, 1H) , 5.06 (d, J 5.2 Hz, 1H) , 4.68 (d, J 7.6 Hz, 1H) , 3.88 (d, J 10.8 Hz, 1H) , 3.69 (s, 3H) , 3.65-3.58 (m, 1H) , 3.34-3.28 (m, 1H) , 3.25-3.16 (m, 2H) , 3.11-3.07 (m, 1H) , 0.85 (s, 9H) , 0.03 (s, 3H) , 0.01 (s, 3H) LC-MS (ESI) : 418.23 [M+NH4]+.

Reference： [1]Patent: WO2016/41470,2016,A1 .Location in patent: Paragraph 0171-0173
[2]Carbohydrate Research,1998,vol. 309,p. 175 - 188
[3]Carbohydrate Research,2008,vol. 343,p. 462 - 469

18
[ 77196-31-7 ]
[ 3150-20-7 ]
[ 473553-39-8 ]

Reference： [1]Tetrahedron,2002,vol. 58,p. 5723 - 5732

19
[ 933-40-4 ]
[ 3150-20-7 ]
[ 854735-96-9 ]

Reference： [1]Tetrahedron,2008,vol. 64,p. 92 - 102

20
[ 3150-20-7 ]
p-methoxyphenyl 2,3-di-O-benzyl-β-D-glucopyranoside [ No CAS ]

Reference： [1]Tetrahedron,2002,vol. 58,p. 5723 - 5732
[2]Tetrahedron,2002,vol. 58,p. 5723 - 5732
[3]Tetrahedron,2002,vol. 58,p. 5723 - 5732
[4]Tetrahedron,2002,vol. 58,p. 5723 - 5732

21
[ 3150-20-7 ]
[ 473553-55-8 ]

Reference： [1]Tetrahedron,2002,vol. 58,p. 5723 - 5732

22
[ 3150-20-7 ]
[ 473553-53-6 ]

Reference： [1]Tetrahedron,2002,vol. 58,p. 5723 - 5732
[2]Tetrahedron,2002,vol. 58,p. 5723 - 5732

23
[ 3150-20-7 ]
[ 473553-42-3 ]

Reference： [1]Tetrahedron,2002,vol. 58,p. 5723 - 5732

24
[ 3150-20-7 ]
[ 278784-76-2 ]