3Ac-SL0101

Base Information

• Chemical Name: 3Ac-SL0101
• CAS No.: 735315-15-8
• Molecular Formula: C27H26O13
• Molecular Weight: 558.496
• Mol file: 735315-15-8.mol

Synonyms:3Ac-SL-0101;

Chemical Property of 3Ac-SL0101

Chemical Property:

• PSA: 188.26000
• LogP: 2.49550

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3Ac-SL0101

There total 13 articles about 3Ac-SL0101 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: 95.0%

(2S,3R,4R,5S,6S)-2-((5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-4-oxo-4H-chromen-3-yl)oxy)-6-methyltetrahydro-2H-pyran-3,4,5-triyl triacetate (910041-19-9) → Kaempferol-3-O-(2,3,4-tri-O-acetyl-alpha-L-rhamnopyranoside) (735315-15-8)

Guidance literature:

With hydrogen; palladium dihydroxide; In tetrahydrofuran; methanol; for 1.5h;

DOI:10.1016/j.bmc.2006.05.009

Reference yield:

5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-3-hydroxy-4H-chromen-4-one (23405-70-1) → Kaempferol-3-O-(2,3,4-tri-O-acetyl-alpha-L-rhamnopyranoside) (735315-15-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 85 percent / PPh₃ / Pd₂(dba)3*CHCl₃ / CH₂Cl₂ / 3 h / 0 °C

2: 73 percent / NaBH₄ / CH₂Cl₂; methanol / 3 h / -78 °C

3: 96 percent / OsO₄; NMO / acetone; 2-methyl-propan-2-ol; H₂O / 3 h / 0 °C

4: 86 percent / DMAP; pyridine / CH₂Cl₂ / 0 °C

5: 86 percent / H₂ / Pd/C / tetrahydrofuran; ethanol / -90 - 20 °C

With pyridine; dmap; sodium tetrahydroborate; osmium(VIII) oxide; N-methyl-2-indolinone; hydrogen; triphenylphosphine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; acetone; tert-butyl alcohol;

DOI:10.1021/ol062076r

Reference yield:

tert-butyl ((2S,6S)-6-methyl-5-oxo-5,6-dihydro-2H-pyran-2-yl) carbonate (865484-73-7) → Kaempferol-3-O-(2,3,4-tri-O-acetyl-alpha-L-rhamnopyranoside) (735315-15-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 85 percent / PPh₃ / Pd₂(dba)3*CHCl₃ / CH₂Cl₂ / 3 h / 0 °C

2: 73 percent / NaBH₄ / CH₂Cl₂; methanol / 3 h / -78 °C

3: 96 percent / OsO₄; NMO / acetone; 2-methyl-propan-2-ol; H₂O / 3 h / 0 °C

4: 86 percent / DMAP; pyridine / CH₂Cl₂ / 0 °C

5: 86 percent / H₂ / Pd/C / tetrahydrofuran; ethanol / -90 - 20 °C

With pyridine; dmap; sodium tetrahydroborate; osmium(VIII) oxide; N-methyl-2-indolinone; hydrogen; triphenylphosphine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; acetone; tert-butyl alcohol;

DOI:10.1021/ol062076r

upstream raw materials:

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

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

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

Downstream raw materials:

Peracetylated-SL₀₁₀₁

Refernces

• 1、 Smith, Jeffrey A.,Maloney, David J.,Clark, David E.,Xu, Yaming,Hecht, Sidney M.,Lannigan, Deborah A.. "Influence of rhamnose substituents on the potency of SL0101, an inhibitor of the Ser/Thr kinase, RSK". . p. 6034 - 6042. Retrieved 2007/10/03.