Ratjadon

Base Information

• Chemical Name: Ratjadon
• CAS No.: 163564-92-9
• Molecular Formula: C₂₈H₄₀O₅
• Molecular Weight: 456.623
• DSSTox Substance ID: DTXSID901043876
• Nikkaji Number: J1.686.005K
• Wikidata: Q104952033
• Mol file: 163564-92-9.mol

Synonyms:(+)-ratjadone;ratjadone;ratjadone A

Chemical Property of Ratjadon

Chemical Property:

• Vapor Pressure: 4.02E-19mmHg at 25°C
• Boiling Point: 640.8°C at 760 mmHg
• Flash Point: 206.8°C
• Density: 1.12g/cm³
• XLogP3: 5.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 9
• Exact Mass: 456.28757437
• Heavy Atom Count: 33
• Complexity: 816

Purity/Quality:

98% ^*data from raw suppliers

RatjadoneA,Synthetic ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC=CC1C(C(CC(O1)C(C=CC=C(C)CC(C)C=C(C)C=CC2CC=CC(=O)O2)O)O)C
• Isomeric SMILES: C/C=C/[C@H]1[C@H]([C@@H](C[C@H](O1)[C@@H](/C=C/C=C(\C)/C[C@@H](C)/C=C(/C)\C=C\[C@H]2CC=CC(=O)O2)O)O)C
• Uses: Ratjadone A, Synthetic is a cell-permeable polyketide that inhibits cell proliferation.

Technology Process of Ratjadon

There total 59 articles about Ratjadon 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: 76.0%

(R)-6-{(1E,3Z,7E,9E)-(5R,11R)-11-(tert-Butyl-dimethyl-silanyloxy)-11-[(2S,4R,5R,6S)-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-6-((E)-propenyl)-tetrahydro-pyran-2-yl]-3,5,7-trimethyl-undeca-1,3,7,9-tetraenyl}-5,6-dihydro-pyran-2-one (321995-12-4) → (+)-ratjadone (163564-92-9)

Guidance literature:

With pyridine; pyridine hydrogenfluoride; In tetrahydrofuran;

DOI:10.1002/1521-3773(20001201)39:23<4364::AID-ANIE4364>3.0.CO;2-G

Reference yield:

(4R)-3-<(E)-(2R,3R)-3-hydroxy-2-methyl-1-oxo-4-hexen-1-yl>-4-(phenylmethyl)-1,3-oxazolidin-2-one (131685-56-8) → (+)-ratjadone (163564-92-9)

Guidance literature:

Multi-step reaction with 16 steps

1.1: Me₃Al / CH₂Cl₂ / -20 - 25 °C

2.1: 2,6-lutidine / CH₂Cl₂ / -78 °C

3.1: Dibal-H / tetrahydrofuran / -78 °C

4.1: BF₃*Et₂O / CH₂Cl₂; diethyl ether / -78 °C

5.1: 2,6-lutidine / CH₂Cl₂ / -78 °C

5.2: Dibal-H / tetrahydrofuran / -78 °C

6.1: mCPBA; NaHCO₃ / CH₂Cl₂ / 0 °C

7.1: 88 percent / TBAF / tetrahydrofuran

8.1: 93 percent / amberlyst-15 / tetrahydrofuran

9.1: 87 percent / 2,6-lutidine / CH₂Cl₂ / -78 °C

10.1: 97 percent / HCl / CHCl₃

11.1: 92 percent / Dess-Martin periodinane / CH₂Cl₂ / 0 °C

12.1: 95 percent / tetrahydrofuran / 0 °C

13.1: 65 percent / Bu₄NBr; Cs₂CO₃; NEt₃ / Pd(OAc)2 / dimethylformamide

14.1: 83 percent / aq. PPTS / acetone

15.1: 77 percent / tetra-n-propylammonium perruthenate; N-methylmorpholine N-oxide; 4 Angstroem molecular sieves / CH₂Cl₂

16.1: 76 percent / HF*pyridine; pyridine / tetrahydrofuran

With pyridine; 2,6-dimethylpyridine; hydrogenchloride; tetrapropylammonium perruthennate; amberlyst-15; 4 A molecular sieve; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; trimethylaluminum; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; sodium hydrogencarbonate; caesium carbonate; Dess-Martin periodane; pyridine hydrogenfluoride; 4-methylmorpholine N-oxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; palladium diacetate; In tetrahydrofuran; diethyl ether; dichloromethane; chloroform; N,N-dimethyl-formamide; acetone; 13.1: Heck reaction;

DOI:10.1002/1521-3773(20001201)39:23<4364::AID-ANIE4364>3.0.CO;2-G

Reference yield:

cis-5,6-dihydro-6-(hydroxymethyl)-2-methoxy-2H-pyran (321994-96-1) → (+)-ratjadone (163564-92-9)

Guidance literature:

Multi-step reaction with 7 steps

1: PPTS

2: 76 percent / t-BuOK / toluene / 0 °C

3: 65 percent / Bu₄NBr; Cs₂CO₃; NEt₃ / Pd(OAc)2 / dimethylformamide

4: 83 percent / aq. PPTS / acetone

5: 77 percent / tetra-n-propylammonium perruthenate; N-methylmorpholine N-oxide; 4 Angstroem molecular sieves / CH₂Cl₂

6: 76 percent / HF*pyridine; pyridine / tetrahydrofuran

With pyridine; tetrapropylammonium perruthennate; 4 A molecular sieve; potassium tert-butylate; tetrabutylammomium bromide; pyridinium p-toluenesulfonate; caesium carbonate; pyridine hydrogenfluoride; 4-methylmorpholine N-oxide; triethylamine; palladium diacetate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; 2: Swern oxidation / 3: Wittig reaction / 4: Heck reaction;

DOI:10.1002/1521-3773(20001201)39:23<4364::AID-ANIE4364>3.0.CO;2-G

upstream raw materials:

(2R,6R)-6-{(1E,3Z,7E,9E)-(5R,11R)-11-Hydroxy-11-[(2S,4R,5S,6S)-4-hydroxy-5-methyl-6-((E)-propenyl)-tetrahydro-pyran-2-yl]-3,5,7-trimethyl-undeca-1,3,7,9-tetraenyl}-5,6-dihydro-2H-pyran-2-ol

(R)-6-{(1E,3Z,7E,9E)-(5R,11R)-11-(tert-Butyl-dimethyl-silanyloxy)-11-[(2S,4R,5R,6S)-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-6-((E)-propenyl)-tetrahydro-pyran-2-yl]-3,5,7-trimethyl-undeca-1,3,7,9-tetraenyl}-5,6-dihydro-pyran-2-one

(4R)-3-<(E)-(2R,3R)-3-hydroxy-2-methyl-1-oxo-4-hexen-1-yl>-4-(phenylmethyl)-1,3-oxazolidin-2-one

cis-5,6-dihydro-6-(hydroxymethyl)-2-methoxy-2H-pyran

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