4-deoxyverrucarol

Base Information

• Chemical Name: 4-deoxyverrucarol
• CAS No.: 91987-94-9
• Molecular Formula: C₁₅H₂₂O₃
• Molecular Weight: 250.338
• Mol file: 91987-94-9.mol

Synonyms:Spiro[2,5-methano-1-benzoxepin-10,2'-oxirane],trichothec-9-en-15-ol deriv.; 4-Deoxyverrucarol

Chemical Property of 4-deoxyverrucarol

Chemical Property:

• Vapor Pressure: 1.22E-06mmHg at 25°C
• Boiling Point: 360.2°Cat760mmHg
• Flash Point: 178.9°C
• Density: 1.21g/cm³

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-deoxyverrucarol

There total 25 articles about 4-deoxyverrucarol 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: 85.0%

(+/-)-(1S*,2S*,5R*,7S*,8S*,9S*,14R*)-8-bromo-14,14-(epoxymethano)-2,9-dimethyl-6,10-dioxatetracyclo[7.2.2.01,7.02,5]tetradecane → (+/-)-4-deoxyverrucarol (91987-94-9)

Guidance literature:

With ammonium chloride; zinc; at 60 ℃;

DOI:10.1016/S0040-4039(99)00047-7

Reference yield:

(+/-)-2-[1-(tert-butyldimethylsilanyloxy)ethyl]acrylic acid methyl ester (118558-96-6) → (+/-)-4-deoxyverrucarol (91987-94-9)

Guidance literature:

Multi-step reaction with 21 steps

1: 96 percent / 1,2-dichloro-benzene / 180 °C

2: H₂ / Pd-C

3: PPTS / Heating

4: DIBAL-H / -78 °C

5: i-Pr₂NEt

6: 97 percent / TBAF / 50 °C

7: 93 percent / Swern oxidation

8: 27 percent / NaH / Heating

9: 85 percent / OsO₄, K₃Fe(CN)6, DABCO, K₂CO₃, MeSO₂NH₂ / 2-methyl-propan-2-ol; H₂O / 0 °C

10: 91 percent / SO₂Cl₂, imidazole, Florisil

11: 97 percent / CeCl₃ / -78 °C

12: 90 percent / Pd(OAc)2

13: DIBAL-H / -78 °C

14: 10 percent HCl

15: 1.) TMSCl, NEt₃; 2.) Pd(OAc)2 / 1.) 100 deg C

16: -78 °C

17: CSA

18: 50 percent / CSA, LiBF₄ / Heating

19: 67 percent / NBS / 0 °C

20: 73 percent / m-CPBA, NaHCO₃

21: 85 percent / Zn, NH₄Cl / 60 °C

With 1,4-diaza-bicyclo[2.2.2]octane; 1H-imidazole; hydrogenchloride; palladium diacetate; florisil; N-Bromosuccinimide; osmium(VIII) oxide; lithium tetrafluoroborate; chloro-trimethyl-silane; sulfuryl dichloride; cerium(III) chloride; methanesulfonamide; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; ammonium chloride; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; potassium hexacyanoferrate(III); zinc; palladium on activated charcoal; In water; 1,2-dichloro-benzene; tert-butyl alcohol;

DOI:10.1016/S0040-4039(99)00047-7

Reference yield:

1-[1-(tert-butyldimethylsiloxy)ethyl]-1-methoxycarbonyl-2-cyclohexen-4-one (224035-85-2) → (+/-)-4-deoxyverrucarol (91987-94-9)

Guidance literature:

Multi-step reaction with 20 steps

1: H₂ / Pd-C

2: PPTS / Heating

3: DIBAL-H / -78 °C

4: i-Pr₂NEt

5: 97 percent / TBAF / 50 °C

6: 93 percent / Swern oxidation

7: 27 percent / NaH / Heating

8: 85 percent / OsO₄, K₃Fe(CN)6, DABCO, K₂CO₃, MeSO₂NH₂ / 2-methyl-propan-2-ol; H₂O / 0 °C

9: 91 percent / SO₂Cl₂, imidazole, Florisil

10: 97 percent / CeCl₃ / -78 °C

11: 90 percent / Pd(OAc)2

12: DIBAL-H / -78 °C

13: 10 percent HCl

14: 1.) TMSCl, NEt₃; 2.) Pd(OAc)2 / 1.) 100 deg C

15: -78 °C

16: CSA

17: 50 percent / CSA, LiBF₄ / Heating

18: 67 percent / NBS / 0 °C

19: 73 percent / m-CPBA, NaHCO₃

20: 85 percent / Zn, NH₄Cl / 60 °C

With 1,4-diaza-bicyclo[2.2.2]octane; 1H-imidazole; hydrogenchloride; palladium diacetate; florisil; N-Bromosuccinimide; osmium(VIII) oxide; lithium tetrafluoroborate; chloro-trimethyl-silane; sulfuryl dichloride; cerium(III) chloride; methanesulfonamide; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; ammonium chloride; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; potassium hexacyanoferrate(III); zinc; palladium on activated charcoal; In water; tert-butyl alcohol;

DOI:10.1016/S0040-4039(99)00047-7

upstream raw materials:

methyl (R)-4,6-O-benzylidene-2(S)-spiro(2,5'-2',5'-dihydrofuran)-2,3-dideoxy-α-D-glucopyranoside

(+/-)-2-[1-(tert-butyldimethylsilanyloxy)ethyl]acrylic acid methyl ester

1-(1-hydroxyethyl)-1-(methoxymethoxy)methyl-4-cyclohexanone ethylene acetal

1-acetyl-1-(methoxymethoxy)methyl-4-cyclohexanone ethylene acetal