Helminthosporol

Base Information

• Chemical Name: Helminthosporol
• CAS No.: 1619-29-0
• Molecular Formula: C₁₅H₂₄O₂
• Molecular Weight: 236.354
• UNII: 7X0G04WG66
• Nikkaji Number: J1.712.018B,J17.186G
• Wikidata: Q110185092
• Mol file: 1619-29-0.mol

Synonyms:helminthosporol

Chemical Property of Helminthosporol

Chemical Property:

• Vapor Pressure: 1.42E-05mmHg at 25°C
• Melting Point: 98°
• Boiling Point: 328.4°Cat760mmHg
• Flash Point: 139.5°C
• PSA: 37.30000
• Density: 1.054g/cm³
• LogP: 2.81240
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 236.177630004
• Heavy Atom Count: 17
• Complexity: 356

Purity/Quality:

99% ^*data from raw suppliers

HELMINTHOSPOROL 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C2C(CCC1(C2CO)C)C(C)C)C=O
• Isomeric SMILES: CC1=C([C@H]2[C@H](CC[C@@]1([C@H]2CO)C)C(C)C)C=O

Technology Process of Helminthosporol

There total 20 articles about Helminthosporol 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: 90.0%

(1S,4S,5R,8S)-4-Isopropyl-8-(4-methoxy-benzyloxymethyl)-1,7-dimethyl-bicyclo[3.2.1]oct-6-ene-6-carbaldehyde (138366-30-0) → (1S,4S,5R,8S)-8-Hydroxymethyl-4-isopropyl-1,7-dimethyl-bicyclo[3.2.1]oct-6-ene-6-carbaldehyde (1619-29-0,10089-26-6,64681-74-9)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; at 0 ℃;

DOI:10.1016/S0040-4039(00)93591-3

Reference yield:

(1R,5R,6R,7R,8S)-8-Benzyloxy-7-hydroxymethyl-5,6-dimethyl-bicyclo[3.2.1]octan-2-ol → (1S,4S,5R,8S)-8-Hydroxymethyl-4-isopropyl-1,7-dimethyl-bicyclo[3.2.1]oct-6-ene-6-carbaldehyde (1619-29-0,10089-26-6,64681-74-9)

Guidance literature:

Multi-step reaction with 15 steps

1: 95 percent / imidazole / dimethylformamide / 24 °C

2: 75 percent / Swern oxidation

3: 77 percent / tetrahydrofuran / -78 - 0 °C

4: 85 percent / KH / tetrahydrofuran; dimethylformamide / ultrasonication

5: 1) Li, liquid NH₃, 2) H₂ / 2) 10percent Pd/C / 1) EtOH/THF, -34 degC, 2) AcOEt, r.t.

6: 98 percent / pyridinium chlorochromate / CH₂Cl₂ / 25 °C

7: 99 percent / KH / tetrahydrofuran / 25 °C

8: 1) BF₃*OEt₂, 2) diisobutylaluminium hydride / 1) CH₂Cl₂/hexane, -78 degC, 10 min, 2) -30 degC

9: 90 percent / KH / tetrahydrofuran; dimethylformamide / 23 °C

10: 90 percent / Bu₄NF / tetrahydrofuran / 25 °C

11: 94 percent / Bu₃P, pyridine / 25 °C

12: 1) m-chloroperbenzoic acid, 2) i-Pr₂NEt / 1) CH₂Cl₂, -42 degC, 2) 190 degC, o-dichlorobenzene

13: 71 percent / SeO₂, t-BuOOH / CH₂Cl₂ / 24 °C

14: 57 percent / PDC / CH₂Cl₂ / 25 °C

15: 90 percent / DDQ / CH₂Cl₂; H₂O / 0 °C

With pyridine; 1H-imidazole; tert.-butylhydroperoxide; dipyridinium dichromate; selenium(IV) oxide; tributylphosphine; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; ammonia; hydrogen; lithium; potassium hydride; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)93591-3

Reference yield:

2-Methoxymethoxy-5,8-dimethyl-6-oxo-tricyclo[3.2.1.02,7]octane-1-carboxylic acid ethyl ester (138366-16-2,138457-05-3) → (1S,4S,5R,8S)-8-Hydroxymethyl-4-isopropyl-1,7-dimethyl-bicyclo[3.2.1]oct-6-ene-6-carbaldehyde (1619-29-0,10089-26-6,64681-74-9)

Guidance literature:

Multi-step reaction with 20 steps

1: NaBH₄ / methanol / 0 °C

2: 94 percent / NaH / tetrahydrofuran; dimethylformamide / 25 °C

3: 91 percent / 36percent HCl / ethanol / 25 °C

4: 99 percent / K₂CO₃ / ethanol

5: 88 percent / LiAlH₄ / diethyl ether / 0 °C

6: 95 percent / imidazole / dimethylformamide / 24 °C

7: 75 percent / Swern oxidation

8: 77 percent / tetrahydrofuran / -78 - 0 °C

9: 85 percent / KH / tetrahydrofuran; dimethylformamide / ultrasonication

10: 1) Li, liquid NH₃, 2) H₂ / 2) 10percent Pd/C / 1) EtOH/THF, -34 degC, 2) AcOEt, r.t.

11: 98 percent / pyridinium chlorochromate / CH₂Cl₂ / 25 °C

12: 99 percent / KH / tetrahydrofuran / 25 °C

13: 1) BF₃*OEt₂, 2) diisobutylaluminium hydride / 1) CH₂Cl₂/hexane, -78 degC, 10 min, 2) -30 degC

14: 90 percent / KH / tetrahydrofuran; dimethylformamide / 23 °C

15: 90 percent / Bu₄NF / tetrahydrofuran / 25 °C

16: 94 percent / Bu₃P, pyridine / 25 °C

17: 1) m-chloroperbenzoic acid, 2) i-Pr₂NEt / 1) CH₂Cl₂, -42 degC, 2) 190 degC, o-dichlorobenzene

18: 71 percent / SeO₂, t-BuOOH / CH₂Cl₂ / 24 °C

19: 57 percent / PDC / CH₂Cl₂ / 25 °C

20: 90 percent / DDQ / CH₂Cl₂; H₂O / 0 °C

With pyridine; 1H-imidazole; hydrogenchloride; tert.-butylhydroperoxide; sodium tetrahydroborate; lithium aluminium tetrahydride; dipyridinium dichromate; selenium(IV) oxide; tributylphosphine; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; ammonia; hydrogen; lithium; potassium hydride; sodium hydride; diisobutylaluminium hydride; potassium carbonate; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)93591-3

upstream raw materials:

(1S,4S,5R,8S)-4-Isopropyl-8-(4-methoxy-benzyloxymethyl)-1,7-dimethyl-bicyclo[3.2.1]oct-6-ene-6-carbaldehyde

(1R,4S,5S,6R,7R,8S)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-4-isopropyl-1,7-dimethyl-bicyclo[3.2.1]octan-8-ol

[(1R,4S,5S,6S,7R,8S)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-4-isopropyl-1,7-dimethyl-bicyclo[3.2.1]oct-8-yl]-methanol

C₂₁H₄₀O₂Si

Downstream raw materials:

(+/-)-helminthosporal

(+/-)-epihelminthosporal

Refernces