3'',4''-Diacetylafzelin

Base Information

• Chemical Name: 3'',4''-Diacetylafzelin
• CAS No.: 77307-50-7
• Molecular Formula: C25H24O12
• Molecular Weight: 516.458
• Hs Code.: 2940000080
• ChEMBL ID: CHEMBL3187298
• NSC Number: 703081
• Wikidata: Q110081617
• Mol file: 77307-50-7.mol

Synonyms:3'',4''-Diacetylafzelin;[4-acetyloxy-6-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy-5-hydroxy-2-methyloxan-3-yl] acetate;[(2S,3S,4S,5R,6S)-4-acetyloxy-6-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy-5-hydroxy-2-methyloxan-3-yl] acetate;3'',4''-O-Diacetylafzelin;CHEMBL3187298;SCHEMBL12693944;CHEBI:176210;HMS3229N19;735315-15-8;HB0584;NSC703081;AKOS024457006;NSC-703081;NCGC00346893-01;SL-0101-1;3-[(3,4-Di-O-acetyl-6-deoxy-?-L-mannopyranosyl)oxy]-5,7-dihydro-2-(4-hydroxyphenyl)-4H-1benzopyran-4-one;3-[(3,4-Di-O-acetyl-6-deoxy-alpha-L-mannopyranosyl)oxy]-5,7-dihydro-2-(4-hydroxyphenyl)-4H -1benzopyran-4-one

Chemical Property of 3'',4''-Diacetylafzelin

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 128-132°C
• Boiling Point: 753.017°C at 760 mmHg
• PKA: 6.20±0.40(Predicted)
• Flash Point: 255.567°C
• PSA: 182.19000
• Density: 1.572g/cm³
• LogP: 1.92470
• Storage Temp.: Store at -20°C
• Solubility.: Acetone (Slightly), Methanol (Slightly)
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 7
• Exact Mass: 516.12677620
• Heavy Atom Count: 37
• Complexity: 909

Purity/Quality:

99% ^*data from raw suppliers

SL 0101-1 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1C(C(C(C(O1)OC2=C(OC3=CC(=CC(=C3C2=O)O)O)C4=CC=C(C=C4)O)O)OC(=O)C)OC(=O)C
• Description: The p90 ribosomal S6 kinases (RSK) 1-4 are downstream members of the extracellular signal-regulated kinase (ERK)/MAPK cascade. SL 0101-1 is a kaempferol glycoside, isolated from the tropical plant F. refracta, that selectively inhibits RSK2 with an IC50 value of 89 nM (Ki = 1 μM) without interfering with upstream activators of RSK, including ERK, MEK, EGFR, and PKC. At 100 μM, SL 0101-1 inhibits the proliferation of MCF-7 breast cancer cells, arresting cells in the G1 phase of the cell cycle. SL 0101-1 has been used to characterize the intracellular signaling events associated with angiotensin II-induced tyrosine kinase activation with a concentration of 30 μM attenuating angiotensin II-induced cell proliferation.
• Uses: A potent and selective inhibitor of p90 Rsk, without inhibiting the function of upstream kinases such as MEK, Raf, or PKC SL 0101 is a potent and selective inhibitor of p90 Rsk, without inhibiting the function of upstream kinases such as MEK, Raf, or PKC.

Technology Process of 3'',4''-Diacetylafzelin

There total 21 articles about 3'',4''-Diacetylafzelin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

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

Guidance literature:

With hydrogen; palladium dihydroxide; In tetrahydrofuran; methanol; for 1h;

DOI:10.1021/ol0500463

Reference yield: 91.0%

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

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene; at 0 ℃; for 1h;

DOI:10.1021/ol062076r

Reference yield:

5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-3-hydroxy-4H-chromen-4-one (23405-70-1) → Kaempferol-3-O-(3,4-O-diacetyl-α-L-rhamnopyranoside) (77307-50-7)

Guidance literature:

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

With pyridine; dmap; sodium tetrahydroborate; osmium(VIII) oxide; N-methyl-2-indolinone; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; In methanol; dichloromethane; water; toluene; tert-butyl alcohol;

DOI:10.1021/ol062076r

upstream raw materials:

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

(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

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

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

Downstream raw materials:

kaempferol 3-rhamnoside

Refernces

• 1、 Shan, Mingde,O'Doherty, George A.. "De novo asymmetric syntheses of SL0101 and its analogues via a palladium-catalyzed glycosylation". . p. 5149 - 5152. Retrieved 2007/10/03.
• 2、 -. "RSK INHIBITORS AND THERAPEUTIC USES THEREOF". Page 50-51. . Retrieved 2008/06/13.