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77307-50-7

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77307-50-7 Usage

Description

SL0101, also known as SL0101-1, is a kaempferol glycoside derived from the tropical plant F. refracta. It is a potent and selective inhibitor of p90 Rsk, specifically RSK2, with an IC50 value of 89 nM (Ki = 1 μM). SL0101-1 does not interfere with upstream activators of RSK, such as ERK, MEK, EGFR, and PKC. It is a tan solid and has been used to study intracellular signaling events associated with angiotensin II-induced tyrosine kinase activation.

Uses

Used in Pharmaceutical Industry:
SL0101 is used as a potent and selective inhibitor of p90 Rsk for targeting the RSK2 enzyme, which plays a role in various cellular processes. Its selectivity allows for specific inhibition without affecting upstream kinases such as MEK, Raf, or PKC.
Used in Cancer Research:
SL0101 is used in cancer research to study the effects of inhibiting RSK2 on the proliferation of cancer cells, such as MCF-7 breast cancer cells. At 100 μM, SL0101-1 arrests cells in the G1 phase of the cell cycle, providing insights into the potential use of RSK2 inhibition in cancer treatment.
Used in Signal Transduction Research:
SL0101 is used in signal transduction research to investigate the role of RSK2 in intracellular signaling events associated with angiotensin II-induced tyrosine kinase activation. A concentration of 30 μM attenuates angiotensin II-induced cell proliferation, offering a tool to study the underlying mechanisms of this process.

Biological Activity

Selective inhibitor of p90 ribosomal S6 kinase (RSK) (IC 50 = 89 nM for RSK2). Does not inhibit upstream kinases such as MEK, Raf and PKC.? Inhibits the growth of MCF-7 human breast cancer cells with no effect on the normal breast cell line.

Check Digit Verification of cas no

The CAS Registry Mumber 77307-50-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 7,7,3,0 and 7 respectively; the second part has 2 digits, 5 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 77307-50:
(7*7)+(6*7)+(5*3)+(4*0)+(3*7)+(2*5)+(1*0)=137
137 % 10 = 7
So 77307-50-7 is a valid CAS Registry Number.
InChI:InChI=1/C25H24O12/c1-10-21(34-11(2)26)24(35-12(3)27)20(32)25(33-10)37-23-19(31)18-16(30)8-15(29)9-17(18)36-22(23)13-4-6-14(28)7-5-13/h4-10,20-21,24-25,28-30,32H,1-3H3/t10-,20+,21?,24?,25?/m0/s1

77307-50-7Synthetic route

5,7-bis(benzyloxy)-2-(4-benzyloxyphenyl)-3-[3,4-di-O-acetyl-2-O-benzyl-α-L-rhamnopyranosyloxy]-4H-chromen-4-one
849938-27-8

5,7-bis(benzyloxy)-2-(4-benzyloxyphenyl)-3-[3,4-di-O-acetyl-2-O-benzyl-α-L-rhamnopyranosyloxy]-4H-chromen-4-one

Kaempferol-3-O-(3,4-O-diacetyl-α-L-rhamnopyranoside)
77307-50-7

Kaempferol-3-O-(3,4-O-diacetyl-α-L-rhamnopyranoside)

Conditions
ConditionsYield
With hydrogen; palladium dihydroxide In tetrahydrofuran; methanol for 1h;94%
With hydrogen; palladium hydroxide on carbon In tetrahydrofuran; methanol for 1h;94%
(2S,3S,4S,5R,6S)-6-((5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-4-oxo-4H-chromen-3- yl)oxy)-5-hydroxy-2-methyltetrahydro-2H-pyran-3,4-diyl diacetate
916069-08-4

(2S,3S,4S,5R,6S)-6-((5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-4-oxo-4H-chromen-3- yl)oxy)-5-hydroxy-2-methyltetrahydro-2H-pyran-3,4-diyl diacetate

Kaempferol-3-O-(3,4-O-diacetyl-α-L-rhamnopyranoside)
77307-50-7

Kaempferol-3-O-(3,4-O-diacetyl-α-L-rhamnopyranoside)

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene at 0℃; for 1h;91%
tert-butyl ((2S,6S)-6-methyl-5-oxo-5,6-dihydro-2H-pyran-2-yl) carbonate
865484-73-7

tert-butyl ((2S,6S)-6-methyl-5-oxo-5,6-dihydro-2H-pyran-2-yl) carbonate

Kaempferol-3-O-(3,4-O-diacetyl-α-L-rhamnopyranoside)
77307-50-7

Kaempferol-3-O-(3,4-O-diacetyl-α-L-rhamnopyranoside)

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: 85 percent / PPh3 / Pd2(dba)3*CHCl3 / CH2Cl2 / 3 h / 0 °C
2.1: 73 percent / NaBH4 / CH2Cl2; methanol / 3 h / -78 °C
3.1: 156 mg / pyridine; DMAP / CH2Cl2 / 1 h / 0 °C
4.1: 77 percent / OsO4; NMO / 2-methyl-propan-2-ol; H2O / 24 h / 0 °C
5.1: p-TsOH*H2O / CH2Cl2 / 0.25 h / 0 °C
5.2: 99 percent / aq. HOAc / CH2Cl2 / 0.25 h / 0 °C
6.1: 62 percent / DBU / toluene / 1 h / 0 °C
7.1: 91 percent / DBU / toluene / 1 h / 0 °C
View Scheme
5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-3-hydroxy-4H-chromen-4-one
23405-70-1

5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-3-hydroxy-4H-chromen-4-one

Kaempferol-3-O-(3,4-O-diacetyl-α-L-rhamnopyranoside)
77307-50-7

Kaempferol-3-O-(3,4-O-diacetyl-α-L-rhamnopyranoside)

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: 85 percent / PPh3 / Pd2(dba)3*CHCl3 / CH2Cl2 / 3 h / 0 °C
2.1: 73 percent / NaBH4 / CH2Cl2; methanol / 3 h / -78 °C
3.1: 156 mg / pyridine; DMAP / CH2Cl2 / 1 h / 0 °C
4.1: 77 percent / OsO4; NMO / 2-methyl-propan-2-ol; H2O / 24 h / 0 °C
5.1: p-TsOH*H2O / CH2Cl2 / 0.25 h / 0 °C
5.2: 99 percent / aq. HOAc / CH2Cl2 / 0.25 h / 0 °C
6.1: 62 percent / DBU / toluene / 1 h / 0 °C
7.1: 91 percent / DBU / toluene / 1 h / 0 °C
View Scheme
Multi-step reaction with 2 steps
1: 60 percent / Ag2O / CH2Cl2 / 4 h / 20 °C
2: 94 percent / H2 / Pd(OH)2/C / tetrahydrofuran; methanol / 1 h
View Scheme
3-((2S,6S)-5,6-dihydro-6-methyl-5-oxo-2H-pyran-2-yloxy)-5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-4H-chromen-4-one
916069-02-8

3-((2S,6S)-5,6-dihydro-6-methyl-5-oxo-2H-pyran-2-yloxy)-5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-4H-chromen-4-one

Kaempferol-3-O-(3,4-O-diacetyl-α-L-rhamnopyranoside)
77307-50-7

Kaempferol-3-O-(3,4-O-diacetyl-α-L-rhamnopyranoside)

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: 73 percent / NaBH4 / CH2Cl2; methanol / 3 h / -78 °C
2.1: 156 mg / pyridine; DMAP / CH2Cl2 / 1 h / 0 °C
3.1: 77 percent / OsO4; NMO / 2-methyl-propan-2-ol; H2O / 24 h / 0 °C
4.1: p-TsOH*H2O / CH2Cl2 / 0.25 h / 0 °C
4.2: 99 percent / aq. HOAc / CH2Cl2 / 0.25 h / 0 °C
5.1: 62 percent / DBU / toluene / 1 h / 0 °C
6.1: 91 percent / DBU / toluene / 1 h / 0 °C
View Scheme
3-((2S,5R,6S)-5,6-dihydro-5-hydroxy-6-methyl-2H-pyran-2-yloxy)-5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-4H-chromen-4-one
916069-03-9

3-((2S,5R,6S)-5,6-dihydro-5-hydroxy-6-methyl-2H-pyran-2-yloxy)-5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-4H-chromen-4-one

Kaempferol-3-O-(3,4-O-diacetyl-α-L-rhamnopyranoside)
77307-50-7

Kaempferol-3-O-(3,4-O-diacetyl-α-L-rhamnopyranoside)

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: 156 mg / pyridine; DMAP / CH2Cl2 / 1 h / 0 °C
2.1: 77 percent / OsO4; NMO / 2-methyl-propan-2-ol; H2O / 24 h / 0 °C
3.1: p-TsOH*H2O / CH2Cl2 / 0.25 h / 0 °C
3.2: 99 percent / aq. HOAc / CH2Cl2 / 0.25 h / 0 °C
4.1: 62 percent / DBU / toluene / 1 h / 0 °C
5.1: 91 percent / DBU / toluene / 1 h / 0 °C
View Scheme
6-(5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-4-oxo-4H-chromen-3-yloxy)-3,6-dihydro-2-methyl-2H-pyran-3-yl acetate
916069-05-1

6-(5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-4-oxo-4H-chromen-3-yloxy)-3,6-dihydro-2-methyl-2H-pyran-3-yl acetate

Kaempferol-3-O-(3,4-O-diacetyl-α-L-rhamnopyranoside)
77307-50-7

Kaempferol-3-O-(3,4-O-diacetyl-α-L-rhamnopyranoside)

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: 77 percent / OsO4; NMO / 2-methyl-propan-2-ol; H2O / 24 h / 0 °C
2.1: p-TsOH*H2O / CH2Cl2 / 0.25 h / 0 °C
2.2: 99 percent / aq. HOAc / CH2Cl2 / 0.25 h / 0 °C
3.1: 62 percent / DBU / toluene / 1 h / 0 °C
4.1: 91 percent / DBU / toluene / 1 h / 0 °C
View Scheme
(2S,3R,4S,5R,6S)-6-((5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-4-oxo-4H-chromen-3-yl)oxy)-4,5-dihydroxy-2-methyltetrahydro-2H-pyran-3-yl acetate
916069-06-2

(2S,3R,4S,5R,6S)-6-((5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-4-oxo-4H-chromen-3-yl)oxy)-4,5-dihydroxy-2-methyltetrahydro-2H-pyran-3-yl acetate

Kaempferol-3-O-(3,4-O-diacetyl-α-L-rhamnopyranoside)
77307-50-7

Kaempferol-3-O-(3,4-O-diacetyl-α-L-rhamnopyranoside)

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: p-TsOH*H2O / CH2Cl2 / 0.25 h / 0 °C
1.2: 99 percent / aq. HOAc / CH2Cl2 / 0.25 h / 0 °C
2.1: 62 percent / DBU / toluene / 1 h / 0 °C
3.1: 91 percent / DBU / toluene / 1 h / 0 °C
View Scheme
(2S,3R,4R,5R,6S)-2-((5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-4-oxo-4H-chromen-3-yl)oxy)-4-hydroxy-6-methyltetrahydro-2H-pyran-3,5-diyl diacetate
916069-07-3

(2S,3R,4R,5R,6S)-2-((5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-4-oxo-4H-chromen-3-yl)oxy)-4-hydroxy-6-methyltetrahydro-2H-pyran-3,5-diyl diacetate

Kaempferol-3-O-(3,4-O-diacetyl-α-L-rhamnopyranoside)
77307-50-7

Kaempferol-3-O-(3,4-O-diacetyl-α-L-rhamnopyranoside)

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 62 percent / DBU / toluene / 1 h / 0 °C
2: 91 percent / DBU / toluene / 1 h / 0 °C
View Scheme
1-(2-furyl)-1-ethanone
1192-62-7

1-(2-furyl)-1-ethanone

Kaempferol-3-O-(3,4-O-diacetyl-α-L-rhamnopyranoside)
77307-50-7

Kaempferol-3-O-(3,4-O-diacetyl-α-L-rhamnopyranoside)

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: 92 percent / formic acid; Et3N / (R)-Ru(η6-mesitylene)-(S,S)-TsDPEN / CH2Cl2 / 24 h / 20 °C
2.1: 90 percent / NaHCO3; NaOAc*3H2O; NBS / tetrahydrofuran; H2O / 1 h / 0 °C
3.1: 60 percent / DMAP / CH2Cl2 / 12 h / -78 °C
4.1: 85 percent / PPh3 / Pd2(dba)3*CHCl3 / CH2Cl2 / 3 h / 0 °C
5.1: 73 percent / NaBH4 / CH2Cl2; methanol / 3 h / -78 °C
6.1: 156 mg / pyridine; DMAP / CH2Cl2 / 1 h / 0 °C
7.1: 77 percent / OsO4; NMO / 2-methyl-propan-2-ol; H2O / 24 h / 0 °C
8.1: p-TsOH*H2O / CH2Cl2 / 0.25 h / 0 °C
8.2: 99 percent / aq. HOAc / CH2Cl2 / 0.25 h / 0 °C
9.1: 62 percent / DBU / toluene / 1 h / 0 °C
10.1: 91 percent / DBU / toluene / 1 h / 0 °C
View Scheme
5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-4H-chromen-4-one
96333-59-4

5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-4H-chromen-4-one

Kaempferol-3-O-(3,4-O-diacetyl-α-L-rhamnopyranoside)
77307-50-7

Kaempferol-3-O-(3,4-O-diacetyl-α-L-rhamnopyranoside)

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: DMSO; 3 Angstroem molecular sieves / acetone; CH2Cl2 / -20 - 0 °C
1.2: 50 percent / TsOH*H2O / CH2Cl2 / 1 h / 20 °C
2.1: 85 percent / PPh3 / Pd2(dba)3*CHCl3 / CH2Cl2 / 3 h / 0 °C
3.1: 73 percent / NaBH4 / CH2Cl2; methanol / 3 h / -78 °C
4.1: 156 mg / pyridine; DMAP / CH2Cl2 / 1 h / 0 °C
5.1: 77 percent / OsO4; NMO / 2-methyl-propan-2-ol; H2O / 24 h / 0 °C
6.1: p-TsOH*H2O / CH2Cl2 / 0.25 h / 0 °C
6.2: 99 percent / aq. HOAc / CH2Cl2 / 0.25 h / 0 °C
7.1: 62 percent / DBU / toluene / 1 h / 0 °C
8.1: 91 percent / DBU / toluene / 1 h / 0 °C
View Scheme
Multi-step reaction with 3 steps
1.1: DMDO / CH2Cl2; acetone / 0 °C
1.2: 78 percent Turnov. / pTsOH / CH2Cl2 / 0.5 h / 0 °C
2.1: 60 percent / Ag2O / CH2Cl2 / 4 h / 20 °C
3.1: 94 percent / H2 / Pd(OH)2/C / tetrahydrofuran; methanol / 1 h
View Scheme
5,7-Dihydroxy-2-(4-hydroxy-phenyl)-chroman-4-on
480-41-1

5,7-Dihydroxy-2-(4-hydroxy-phenyl)-chroman-4-on

Kaempferol-3-O-(3,4-O-diacetyl-α-L-rhamnopyranoside)
77307-50-7

Kaempferol-3-O-(3,4-O-diacetyl-α-L-rhamnopyranoside)

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: 75 percent / K2CO3 / acetone / 6 h / Heating
2.1: 76 percent / I2 / dimethylsulfoxide / 24 h / 110 °C
3.1: DMSO; 3 Angstroem molecular sieves / acetone; CH2Cl2 / -20 - 0 °C
3.2: 50 percent / TsOH*H2O / CH2Cl2 / 1 h / 20 °C
4.1: 85 percent / PPh3 / Pd2(dba)3*CHCl3 / CH2Cl2 / 3 h / 0 °C
5.1: 73 percent / NaBH4 / CH2Cl2; methanol / 3 h / -78 °C
6.1: 156 mg / pyridine; DMAP / CH2Cl2 / 1 h / 0 °C
7.1: 77 percent / OsO4; NMO / 2-methyl-propan-2-ol; H2O / 24 h / 0 °C
8.1: p-TsOH*H2O / CH2Cl2 / 0.25 h / 0 °C
8.2: 99 percent / aq. HOAc / CH2Cl2 / 0.25 h / 0 °C
9.1: 62 percent / DBU / toluene / 1 h / 0 °C
10.1: 91 percent / DBU / toluene / 1 h / 0 °C
View Scheme
L-aculose
247244-65-1

L-aculose

Kaempferol-3-O-(3,4-O-diacetyl-α-L-rhamnopyranoside)
77307-50-7

Kaempferol-3-O-(3,4-O-diacetyl-α-L-rhamnopyranoside)

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: 60 percent / DMAP / CH2Cl2 / 12 h / -78 °C
2.1: 85 percent / PPh3 / Pd2(dba)3*CHCl3 / CH2Cl2 / 3 h / 0 °C
3.1: 73 percent / NaBH4 / CH2Cl2; methanol / 3 h / -78 °C
4.1: 156 mg / pyridine; DMAP / CH2Cl2 / 1 h / 0 °C
5.1: 77 percent / OsO4; NMO / 2-methyl-propan-2-ol; H2O / 24 h / 0 °C
6.1: p-TsOH*H2O / CH2Cl2 / 0.25 h / 0 °C
6.2: 99 percent / aq. HOAc / CH2Cl2 / 0.25 h / 0 °C
7.1: 62 percent / DBU / toluene / 1 h / 0 °C
8.1: 91 percent / DBU / toluene / 1 h / 0 °C
View Scheme
Kaempferol-3-O-(3,4-O-diacetyl-α-L-rhamnopyranoside)
77307-50-7

Kaempferol-3-O-(3,4-O-diacetyl-α-L-rhamnopyranoside)

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1.1: 90 percent / NaHCO3; NaOAc*3H2O; NBS / tetrahydrofuran; H2O / 1 h / 0 °C
2.1: 60 percent / DMAP / CH2Cl2 / 12 h / -78 °C
3.1: 85 percent / PPh3 / Pd2(dba)3*CHCl3 / CH2Cl2 / 3 h / 0 °C
4.1: 73 percent / NaBH4 / CH2Cl2; methanol / 3 h / -78 °C
5.1: 156 mg / pyridine; DMAP / CH2Cl2 / 1 h / 0 °C
6.1: 77 percent / OsO4; NMO / 2-methyl-propan-2-ol; H2O / 24 h / 0 °C
7.1: p-TsOH*H2O / CH2Cl2 / 0.25 h / 0 °C
7.2: 99 percent / aq. HOAc / CH2Cl2 / 0.25 h / 0 °C
8.1: 62 percent / DBU / toluene / 1 h / 0 °C
9.1: 91 percent / DBU / toluene / 1 h / 0 °C
View Scheme
(E)-1-(2,4-bis(benzyloxy)-6-hydroxyphenyl)-3-(4-(benzyloxy)phenyl)prop-2-en-1-one
88607-79-8

(E)-1-(2,4-bis(benzyloxy)-6-hydroxyphenyl)-3-(4-(benzyloxy)phenyl)prop-2-en-1-one

Kaempferol-3-O-(3,4-O-diacetyl-α-L-rhamnopyranoside)
77307-50-7

Kaempferol-3-O-(3,4-O-diacetyl-α-L-rhamnopyranoside)

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1.1: 76 percent / I2 / dimethylsulfoxide / 24 h / 110 °C
2.1: DMSO; 3 Angstroem molecular sieves / acetone; CH2Cl2 / -20 - 0 °C
2.2: 50 percent / TsOH*H2O / CH2Cl2 / 1 h / 20 °C
3.1: 85 percent / PPh3 / Pd2(dba)3*CHCl3 / CH2Cl2 / 3 h / 0 °C
4.1: 73 percent / NaBH4 / CH2Cl2; methanol / 3 h / -78 °C
5.1: 156 mg / pyridine; DMAP / CH2Cl2 / 1 h / 0 °C
6.1: 77 percent / OsO4; NMO / 2-methyl-propan-2-ol; H2O / 24 h / 0 °C
7.1: p-TsOH*H2O / CH2Cl2 / 0.25 h / 0 °C
7.2: 99 percent / aq. HOAc / CH2Cl2 / 0.25 h / 0 °C
8.1: 62 percent / DBU / toluene / 1 h / 0 °C
9.1: 91 percent / DBU / toluene / 1 h / 0 °C
View Scheme
Multi-step reaction with 4 steps
1.1: 72 percent / I2 / dimethylsulfoxide / 140 °C
2.1: DMDO / CH2Cl2; acetone / 0 °C
2.2: 78 percent Turnov. / pTsOH / CH2Cl2 / 0.5 h / 0 °C
3.1: 60 percent / Ag2O / CH2Cl2 / 4 h / 20 °C
4.1: 94 percent / H2 / Pd(OH)2/C / tetrahydrofuran; methanol / 1 h
View Scheme
phenyl 2-O-benzyl-1-thio-α-L-rhamnopyranoside
849938-16-5

phenyl 2-O-benzyl-1-thio-α-L-rhamnopyranoside

Kaempferol-3-O-(3,4-O-diacetyl-α-L-rhamnopyranoside)
77307-50-7

Kaempferol-3-O-(3,4-O-diacetyl-α-L-rhamnopyranoside)

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 100 percent / Et3N; DMAP / CH2Cl2 / 20 °C
2: 84 percent / Br2 / CH2Cl2 / 1 h / 0 °C
3: 60 percent / Ag2O / CH2Cl2 / 4 h / 20 °C
4: 94 percent / H2 / Pd(OH)2/C / tetrahydrofuran; methanol / 1 h
View Scheme
3,4-di-O-acetyl-2-O-benzyl-α-L-rhamnopyranosyl bromide
849938-23-4

3,4-di-O-acetyl-2-O-benzyl-α-L-rhamnopyranosyl bromide

Kaempferol-3-O-(3,4-O-diacetyl-α-L-rhamnopyranoside)
77307-50-7

Kaempferol-3-O-(3,4-O-diacetyl-α-L-rhamnopyranoside)

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 60 percent / Ag2O / CH2Cl2 / 4 h / 20 °C
2: 94 percent / H2 / Pd(OH)2/C / tetrahydrofuran; methanol / 1 h
View Scheme
phenyl 3,4-di-O-acetyl-2-O-benzyl-1-thio-α-L-rhamnopyranoside
849938-20-1

phenyl 3,4-di-O-acetyl-2-O-benzyl-1-thio-α-L-rhamnopyranoside

Kaempferol-3-O-(3,4-O-diacetyl-α-L-rhamnopyranoside)
77307-50-7

Kaempferol-3-O-(3,4-O-diacetyl-α-L-rhamnopyranoside)

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 84 percent / Br2 / CH2Cl2 / 1 h / 0 °C
2: 60 percent / Ag2O / CH2Cl2 / 4 h / 20 °C
3: 94 percent / H2 / Pd(OH)2/C / tetrahydrofuran; methanol / 1 h
View Scheme
naringenin
480-41-1

naringenin

Kaempferol-3-O-(3,4-O-diacetyl-α-L-rhamnopyranoside)
77307-50-7

Kaempferol-3-O-(3,4-O-diacetyl-α-L-rhamnopyranoside)

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: 81 percent / K2CO3 / acetone / Heating
2.1: 72 percent / I2 / dimethylsulfoxide / 140 °C
3.1: DMDO / CH2Cl2; acetone / 0 °C
3.2: 78 percent Turnov. / pTsOH / CH2Cl2 / 0.5 h / 0 °C
4.1: 60 percent / Ag2O / CH2Cl2 / 4 h / 20 °C
5.1: 94 percent / H2 / Pd(OH)2/C / tetrahydrofuran; methanol / 1 h
View Scheme
C85H88O11Si3

C85H88O11Si3

Kaempferol-3-O-(3,4-O-diacetyl-α-L-rhamnopyranoside)
77307-50-7

Kaempferol-3-O-(3,4-O-diacetyl-α-L-rhamnopyranoside)

C89H96O12Si4

C89H96O12Si4

Kaempferol-3-O-(3,4-O-diacetyl-α-L-rhamnopyranoside)
77307-50-7

Kaempferol-3-O-(3,4-O-diacetyl-α-L-rhamnopyranoside)

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran
acetic anhydride
108-24-7

acetic anhydride

Kaempferol-3-O-(3,4-O-diacetyl-α-L-rhamnopyranoside)
77307-50-7

Kaempferol-3-O-(3,4-O-diacetyl-α-L-rhamnopyranoside)

Acetic acid (2S,3R,4R,5S,6S)-4,5-diacetoxy-2-[7-acetoxy-2-(4-acetoxy-phenyl)-5-hydroxy-4-oxo-4H-chromen-3-yloxy]-6-methyl-tetrahydro-pyran-3-yl ester

Acetic acid (2S,3R,4R,5S,6S)-4,5-diacetoxy-2-[7-acetoxy-2-(4-acetoxy-phenyl)-5-hydroxy-4-oxo-4H-chromen-3-yloxy]-6-methyl-tetrahydro-pyran-3-yl ester

Conditions
ConditionsYield
With pyridine at 23℃; for 1h;
acetic anhydride
108-24-7

acetic anhydride

Kaempferol-3-O-(3,4-O-diacetyl-α-L-rhamnopyranoside)
77307-50-7

Kaempferol-3-O-(3,4-O-diacetyl-α-L-rhamnopyranoside)

Peracetylated-SL0101
72165-31-2

Peracetylated-SL0101

Conditions
ConditionsYield
With pyridine
Kaempferol-3-O-(3,4-O-diacetyl-α-L-rhamnopyranoside)
77307-50-7

Kaempferol-3-O-(3,4-O-diacetyl-α-L-rhamnopyranoside)

kaempferol 3-rhamnoside
482-39-3, 22334-39-0, 28978-08-7

kaempferol 3-rhamnoside

Conditions
ConditionsYield
With sodium hydroxide In methanol at 23℃; for 0.333333h;9 mg
With potassium carbonate In methanol

77307-50-7Downstream Products

77307-50-7Relevant articles and documents

SYNTHESIS OF INHIBITORS OF P90RSK

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Page/Page column 5; 30; 35, (2008/06/13)

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Synthesis of a potent and selective inhibitor of p90 Rsk

Maloney, David J.,Hecht, Sidney M.

, p. 1097 - 1099 (2007/10/03)

(Chemical Equation Presented) The synthesis of the naturally occurring kaempferol glycoside SL0101 has been accomplished, as has its biochemical evaluation. SL0101 exhibits selective and potent p90 Rsk inhibitory activity at nanomolar concentrations without inhibiting the function of upstream kinases such as MEK, Raf, or PKC. The synthesis verified the structural assignment of the natural product and has provided access to material sufficient for detailed biological evaluation.

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