Name: bullatacin
SKU: 102989-24-2

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Basic Information

Molecular Structure:
CAS No.:	102989-24-2
Name:	bullatacin
Article Data:	8

Formula:	C37H66 O7
Molecular Weight:	622.927
Synonyms:	2(5H)-Furanone,3-[2,13-dihydroxy-13-[octahydro-5'-(1-hydroxyundecyl)[2,2'-bifuran]-5-yl]tridecyl]-5-methyl-,[2R-[2a[2'R,5'R(R)],5b[2R(S),13R]]]-; (+)-Asimicin;Asimicin; Squamocin H
Density:	1.054g/cm³
Melting Point:	45-48 °C(Solv: methanol (67-56-1); water (7732-18-5))
Boiling Point:	745.5°Cat760mmHg
Flash Point:	220.3°C
PSA:	105.45000
LogP:	7.85790

Synthetic route

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In aq. phosphate buffer; water; 1,2-dichloro-ethane at 50℃; for 2h;	98%

Conditions	Yield
With hydrogen fluoride In tetrahydrofuran; acetonitrile at 20℃; for 12h; Inert atmosphere;	91%

: (S)-3-{(2S,13S)-2-(tert-Butyl-dimethyl-silanyloxy)-13-methoxymethoxy-13-[(2R,5R,2'R,5'R)-5'-((S)-1-methoxymethoxy-undecyl)-octahydro-[2,2']bifuranyl-5-yl]-tridecyl}-5-methyl-5H-furan-2-one

Conditions	Yield
With acetyl chloride In methanol; dichloromethane at 20℃; for 2h; Elimination;	83%

: 193812-20-3
(S)-3-((2R,13R)-2,13-Bis-(2-trimethylsilanyl-ethoxymethoxy)-13-{(2R,5R,2'R,5'R)-5'-[(R)-1-(2-trimethylsilanyl-ethoxymethoxy)-undecyl]-octahydro-[2,2']bifuranyl-5-yl}-tridecyl)-5-methyl-5H-furan-2-one

Conditions	Yield
With pyridinium p-toluenesulfonate In ethanol at 40℃; for 16h;	67%

: 507480-65-1
(S)-3-{(2R,13R)-2-Hydroxy-13-methoxymethoxy-13-[(2R,5R,2'R,5'R)-5'-((R)-1-methoxymethoxy-undecyl)-octahydro-[2,2']bifuranyl-5-yl]-tridecyl}-5-methyl-5H-furan-2-one

Conditions	Yield
With hydrogenchloride In tetrahydrofuran; methanol at 20℃; for 15h;	57%

: (S)-3-{(E)-(2R,13R)-2-(tert-Butyl-diphenyl-silanyloxy)-13-hydroxy-13-[(2R,5R,2'R,5'R)-5'-((R)-1-hydroxy-undecyl)-octahydro-[2,2']bifuranyl-5-yl]-tridec-8-en-10-ynyl}-5-methyl-5H-furan-2-one

Conditions	Yield
With Wilkinson's catalyst; hydrogen; acetyl chloride 1.) benzene,2.) MeOH, Et2O; Yield given. Multistep reaction;

: (S)-3-{(2R,13R)-2,13-Bis-methoxymethoxy-13-[(2R,5R,2'R,5'R)-5'-((R)-1-methoxymethoxy-undecyl)-octahydro-[2,2']bifuranyl-5-yl]-tridecyl}-5-methyl-5H-furan-2-one

Conditions	Yield
With dimethylsulfide; boron trifluoride diethyl etherate In dichloromethane for 0.5h; 0 deg C -> r.t.;

: Trifluoro-acetic acid (1R,12R)-13-((S)-5-methyl-2-oxo-2,5-dihydro-furan-3-yl)-12-(2,2,2-trifluoro-acetoxy)-1-{(2R,5R,2'R,5'R)-5'-[(R)-1-(2,2,2-trifluoro-acetoxy)-undecyl]-octahydro-[2,2']bifuranyl-5-yl}-tridecyl ester

Conditions	Yield
With potassium cyanide In methanol for 0.333333h;

: 863604-39-1
(2R,4R,5S)-5-[(1R)-1-(tert-butyldimethylsilanyloxy)undecyl]-4-(dimethylphanylsilanyl)tetrahydrofuran-2-carbaldehyde

Conditions	Yield
Multi-step reaction with 6 steps 1: 4 Angstroem molecular sieves; SnCl4 / CH2Cl2 / -40 °C 2: TBAF / dimethylformamide; tetrahydrofuran / 6 h / 90 °C 3: 0.5 h / 20 °C 4: Pd(PPh3)4; water / tetrahydrofuran / 2 h / 20 °C 5: AgNO3/SiO2 / hexane; CH2Cl2 / 2 h 6: KCN / methanol / 0.33 h View Scheme
Multi-step reaction with 6 steps 1: 4 Angstroem molecular sieves; SnCl4 / CH2Cl2 / 4 h / 0 °C 2: TBAF / dimethylformamide; tetrahydrofuran / 6 h / 90 °C 3: 0.5 h / 20 °C 4: Pd(PPh3)4; water / tetrahydrofuran / 2 h / 20 °C 5: AgNO3/SiO2 / hexane; CH2Cl2 / 2 h 6: KCN / methanol / 0.33 h View Scheme

: 863604-46-0
(2R,4R,5S)-[5-[(1R)-1-(tert-butyldimethylsilanyloxy)undecyl]-4-(dimethylphenylsilanyl)tetrahydrofuran-2-yl]methanol

Conditions	Yield
Multi-step reaction with 7 steps 1: diisopropylethyl amine; DMSO; SO3*pyridine / CH2Cl2 / 1 h / 0 °C 2: 4 Angstroem molecular sieves; SnCl4 / CH2Cl2 / -40 °C 3: TBAF / dimethylformamide; tetrahydrofuran / 6 h / 90 °C 4: 0.5 h / 20 °C 5: Pd(PPh3)4; water / tetrahydrofuran / 2 h / 20 °C 6: AgNO3/SiO2 / hexane; CH2Cl2 / 2 h 7: KCN / methanol / 0.33 h View Scheme
Multi-step reaction with 7 steps 1: diisopropylethyl amine; DMSO; SO3*pyridine / CH2Cl2 / 1 h / 0 °C 2: 4 Angstroem molecular sieves; SnCl4 / CH2Cl2 / 4 h / 0 °C 3: TBAF / dimethylformamide; tetrahydrofuran / 6 h / 90 °C 4: 0.5 h / 20 °C 5: Pd(PPh3)4; water / tetrahydrofuran / 2 h / 20 °C 6: AgNO3/SiO2 / hexane; CH2Cl2 / 2 h 7: KCN / methanol / 0.33 h View Scheme

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