CAS No. :	7493-95-0
Formula :	C₁₂H₁₅NO₈
M.W :	301.25
SMILES Code :	O[C@H]1[C@@H](CO)O[C@H](OC2=CC=C([N+]([O-])=O)C=C2)[C@H](O)[C@H]1O
Synonyms :	PNP-α-D-Gal; PNP-alpha-D-Gal
MDL No. :	MFCD00065050
InChI Key :	IFBHRQDFSNCLOZ-IIRVCBMXSA-N
Pubchem ID :	82000

Safety of 4-Nitrophenyl α-D-galactopyranoside

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

Application In Synthesis of 4-Nitrophenyl α-D-galactopyranoside

* 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 [ 7493-95-0 ]

[ 7493-95-0 ] Synthesis Path-Downstream 1~54

1
[ 17042-39-6 ]
[ 7493-95-0 ]

References: [1]Justus Liebigs Annalen der Chemie,1954,vol. 589,p. 77,79.
Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie,1958,vol. 311,p. 54,58.
[2]Canadian Journal of Chemistry,1981,vol. 59,p. 314 - 320.

2
[ 7493-95-0 ]
[ 3398-86-5 ]

References: [1]Bulletin of the Chemical Society of Japan,2000,vol. 73,p. 2553 - 2558.
[2]Chemische Berichte,1956,vol. 89,p. 582,587.
[3]Journal of Agricultural and Food Chemistry,2004,vol. 52,p. 7453 - 7456.

3
[ 1824-94-8 ]
[ 7493-95-0 ]
[ 18449-79-1 ]
[ 81131-45-5 ]

References: [1]Carbohydrate Research,1987,vol. 167,p. 95 - 104.

4
[ 3396-99-4 ]
[ 7493-95-0 ]
[ 104420-77-1 ]

References: [1]Chemical Communications,1999,p. 2065 - 2066.
[2]Carbohydrate Research,1987,vol. 167,p. 95 - 104.

5
[ 108-24-7 ]
[ 48149-72-0 ]
[ 7493-95-0 ]
[ 120095-03-6 ]

References: [1]Carbohydrate Research,1988,vol. 180,p. 53 - 60.

6
[ 108-24-7 ]
[ 72377-14-1 ]
[ 7493-95-0 ]
Acetic acid (2R,3R,4R,5R,6S)-2-acetoxymethyl-5-acetylamino-6-ethoxy-4-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester [ No CAS ]

References: [1]Carbohydrate research,1989,vol. 188,p. 9 - 17.

7
[ 5382-00-3 ]
[ 7493-95-0 ]
[ 114102-82-8 ]

References: [1]Carbohydrate Research,1987,vol. 165,p. 1 - 16.

8
[ 100-52-7 ]
[ 7493-95-0 ]
[ 85906-27-0 ]

References: [1]Journal of the Chemical Society. Perkin Transactions 2 (2001),1998,p. 2585 - 2591.
[2]Carbohydrate Research,1983,vol. 114,p. 322 - 327.

9
[ 100-44-7 ]
[ 7493-95-0 ]
[ 77988-32-0 ]
[ 64768-18-9 ]

References: [1]Canadian Journal of Chemistry,1981,vol. 59,p. 314 - 320.
[2]Canadian Journal of Chemistry,1981,vol. 59,p. 314 - 320.

10
[ 7493-95-0 ]
[ 10257-28-0 ]
[ 100-02-7 ]

References: [1]Phytochemistry,1981,vol. 20,p. 45 - 48.
[2]Phytochemistry,1993,vol. 33,p. 1327 - 1332.
[3]Carbohydrate Research,1996,vol. 296,p. 261 - 273.
[4]Chemistry Letters,1998,p. 1077 - 1078.
[5]Carbohydrate Research,2000,vol. 324,p. 107 - 115.
[6]Phytochemistry,2001,vol. 58,p. 995 - 1005.
[7]Journal of Organic Chemistry,2005,vol. 70,p. 7217 - 7226.
[8]European Journal of Organic Chemistry,2012,p. 5366 - 5372.

11
[ 7493-95-0 ]
[ 100-02-7 ]

Yield	Reaction Conditions	Operation in experiment
	With Bacillus stearothermophillus alpha-glucosidase; water; at 37.0℃;pH 7.0;aq. phosphate buffer; Enzymatic reaction;Kinetics;	General procedure: Enzymatic reactions were performed as follows: a 1 muL aliquot of alpha-glucosidase stock solution (2.5 × 10-5 mg/mL) was placed onto the wall of each well of a 96-well plate containing 199 muL substrate (0-200 mM) and 100 mM phosphate buffer solution (pH 7.0), and incubated at 37 C for 3 min. The hydrolysis reaction was started by shaking the plate, thus mixing together the enzyme and buffer. The initial slopes of the absorbance at 405 nm against incubation time were converted into initial velocities using the molar extinction co-efficient of p-nitrophenol at 405 nm (10900 cm-1 M-1). The initial velocities were estimated as the average of five measurements.The hydrolysis of substrates during the incubation time in the absence of enzyme was negligible ([p-nitrophenol]background <6.5 × 10-7 mM min-1) even in the presence of solute 6 (0-1000 mM).

References: [1]Phytochemistry,1990,vol. 29,p. 2425 - 2429.
[2]Phytochemistry,2001,vol. 58,p. 213 - 219.
[3]Bioorganic and Medicinal Chemistry,2003,vol. 11,p. 3559 - 3568.
[4]Bioscience, Biotechnology and Biochemistry,2003,vol. 67,p. 2160 - 2166.
[5]Bioorganic and Medicinal Chemistry,2007,vol. 15,p. 2016 - 2023.
[6]Russian Journal of Applied Chemistry,2006,vol. 79,p. 827 - 832.
[7]Bioscience, Biotechnology and Biochemistry,2008,vol. 72,p. 2203 - 2205.
[8]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 3790 - 3794.
[9]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 3128 - 3134.
[10]Food Chemistry,2011,vol. 126,p. 177 - 182.
[11]Journal of Biological Chemistry,2011,vol. 286,p. 40814 - 40823.
[12]Tetrahedron Letters,2012,vol. 53,p. 5023 - 5026.
[13]Journal of Organic Chemistry,2012,vol. 77,p. 7873 - 7882.
[14]RSC Advances,2015,vol. 5,p. 55313 - 55320.
[15]International Journal of Biological Macromolecules,2019,vol. 128,p. 324 - 330.

12
[ 7493-95-0 ]
p-nitrophenyl 3-O-α-D-galactopyranosyl-α-D-galactopyranoside [ No CAS ]
p-nitrophenyl 2-O-α-D-galactopyranosyl-α-D-galactopyranoside [ No CAS ]

References: [1]Carbohydrate Research,1987,vol. 167,p. 95 - 104.

13
[ 67-64-1 ]
[ 7493-95-0 ]
[ 29781-32-6 ]
[ 29781-31-5 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1982,p. 2973 - 2982.

14
[ 27891-73-2 ]
[ 7493-95-0 ]
(2R,3R,4S,5R,6R)-2-[(2S,3R,4S,5S,6R)-2-((2R,3S,4R,5R,6S)-4,5-Dihydroxy-2-hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3-yloxy)-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol [ No CAS ]
C₂₄H₃₆O₁₅S [ No CAS ]

References: [1]Chemical Communications,1996,p. 1473 - 1474.

15
[ 131070-86-5 ]
[ 7493-95-0 ]
(2R,3R,4S,5R,6R)-2-[(2S,3R,4S,5S,6R)-2-((2R,3S,4R,5R,6S)-6-Ethylsulfanyl-4,5-dihydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy)-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol [ No CAS ]
C₂₀H₃₆O₁₅S [ No CAS ]

References: [1]Chemical Communications,1996,p. 1473 - 1474.

16
[ 131070-86-5 ]
[ 7493-95-0 ]
(2R,3R,4S,5R,6R)-2-[(2S,3R,4S,5S,6R)-2-((2R,3S,4R,5R,6S)-6-Ethylsulfanyl-4,5-dihydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy)-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol [ No CAS ]
C₂₀H₃₆O₁₅S [ No CAS ]

References: [1]Chemical Communications,1996,p. 1473 - 1474.

17
[ 131070-86-5 ]
[ 7493-95-0 ]
C₂₀H₃₆O₁₅S [ No CAS ]

References: [1]Chemical Communications,1996,p. 1473 - 1474.

18
(2S,3R,4S,5R,6R)-2-((2R,3S,4R,5R,6S)-6-Butylsulfanyl-4,5-dihydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol [ No CAS ]
[ 7493-95-0 ]
(2R,3R,4S,5R,6R)-2-[(2S,3R,4S,5S,6R)-2-((2R,3S,4R,5R,6S)-6-Butylsulfanyl-4,5-dihydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy)-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol [ No CAS ]
C₂₂H₄₀O₁₅S [ No CAS ]

References: [1]Chemical Communications,1996,p. 1473 - 1474.

19
[ 167554-00-9 ]
[ 7493-95-0 ]
C₂₂H₃₉NO₁₅S [ No CAS ]
N-{(2S,3R,4R,5S,6R)-2-Ethylsulfanyl-4-hydroxy-6-hydroxymethyl-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-2-yloxy]-tetrahydro-pyran-3-yl}-acetamide [ No CAS ]

References: [1]Chemical Communications,1997,p. 169 - 170.
[2]Chemical Communications,1997,p. 169 - 170.

20
[ 7493-95-0 ]
[ 110891-71-9 ]
4-nitrophenyl (α-D-galactopyranosyl)-(1->2)-α-D-galactopyranoside [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1997,vol. 7,p. 255 - 258.

21
[ 7493-95-0 ]
[ 187394-28-1 ]

References: [1]FEBS Journal,2010,vol. 277,p. 3538 - 3551.
[2]Carbohydrate Research,1996,vol. 296,p. 261 - 273.

22
[ 186665-12-3 ]
[ 7493-95-0 ]
[ 110891-71-9 ]
Galα1-3Galβ1-4GlcNTeocβ-SEt [ No CAS ]

References: [1]Tetrahedron Letters,1997,vol. 38,p. 133 - 136.

23
[ 186665-12-3 ]
[ 7493-95-0 ]
Galα1-3Galβ1-4GlcNTeocβ-SEt [ No CAS ]

References: [1]Tetrahedron Letters,1997,vol. 38,p. 133 - 136.

24
[ 19130-96-2 ]
[ 7493-95-0 ]
6-O-(α-D-galactopyranosyl)-1-deoxynojirimycin [ No CAS ]

References: [1]Bioscience, Biotechnology and Biochemistry,1998,vol. 62,p. 588 - 589.

25
[ 2390-99-0 ]
[ 7493-95-0 ]
(2R,3R,4S,5R,6S)-2-Hydroxymethyl-6-[(E)-2-methyl-3-((4R,5R)-4-methylamino-1,3,4,5-tetrahydro-benzo[cd]indol-5-yl)-allyloxy]-tetrahydro-pyran-3,4,5-triol [ No CAS ]

References: [1]Journal of Carbohydrate Chemistry,1998,vol. 17,p. 981 - 986.

26
[ 548-43-6 ]
[ 7493-95-0 ]
(2R,3R,4S,5R,6R)-2-[(2R,3S,4S,5R,6S)-3,5-Dihydroxy-2-hydroxymethyl-6-((6aR,10aR)-7-methyl-4,6,6a,7,8,10a-hexahydro-indolo[4,3-fg]quinolin-9-ylmethoxy)-tetrahydro-pyran-4-yloxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol [ No CAS ]
(2R,3R,4S,5R,6S)-2-Hydroxymethyl-6-((6aR,10aR)-7-methyl-4,6,6a,7,8,10a-hexahydro-indolo[4,3-fg]quinolin-9-ylmethoxy)-tetrahydro-pyran-3,4,5-triol [ No CAS ]

References: [1]Journal of Carbohydrate Chemistry,1998,vol. 17,p. 981 - 986.

27
[ 67-56-1 ]
[ 7493-95-0 ]
[ 3396-99-4 ]