Ascofuranol

Base Information

• Chemical Name: Ascofuranol
• CAS No.: 51759-79-6
• Molecular Formula: C23H31ClO5
• Molecular Weight: 422.949
• Nikkaji Number: J157.889H
• Wikidata: Q105348663
• Pharos Ligand ID: AS6KLAH9GCJP
• Metabolomics Workbench ID: 98102
• ChEMBL ID: CHEMBL4865354
• Mol file: 51759-79-6.mol

Synonyms:ascofuranol

Chemical Property of Ascofuranol

Chemical Property:

• Vapor Pressure: 1.03E-14mmHg at 25°C
• Boiling Point: 588.9°Cat760mmHg
• Flash Point: 310°C
• PSA: 86.99000
• Density: 1.211g/cm³
• LogP: 5.01580
• XLogP3: 5.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 422.1860018
• Heavy Atom Count: 29
• Complexity: 629

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(=C(C(=C1Cl)O)CC=C(C)CCC=C(C)C2CC(C(O2)(C)C)O)O)C=O
• Isomeric SMILES: CC1=C(C(=C(C(=C1Cl)O)C/C=C(\C)/CC/C=C(\C)/[C@@H]2C[C@@H](C(O2)(C)C)O)O)C=O

Technology Process of Ascofuranol

There total 10 articles about Ascofuranol 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: 71.0%

(2'E,6'E,1''S,4''S)-5-chloro-2,4-dihydroxy-6-methyl-3-<7'-(4''-t-butyldimethylsilyloxy-3'',3''-dimethyl-2''-oxacyclopentyl)-3',7'-dimethyl-2',6'-heptadienyl>benzaldehyde (99477-63-1) → (1''S,4''S)-(-)-ascofuranol (51759-79-6,99529-62-1)

Guidance literature:

With hydrogen fluoride; In water; acetonitrile; for 1h; Ambient temperature;

DOI:10.1016/S0040-4020(01)96657-8

Reference yield:

(2E,6E,1'S,4'S)-(+)-7-(4'-hydroxy-3',3'-dimethyl-2'-oxacyclopentyl)-3,7-dimethyl-2,6-heptadienyl acetate (99529-56-3) → (1''S,4''S)-(-)-ascofuranol (51759-79-6,99529-62-1)

Guidance literature:

Multi-step reaction with 8 steps

1: imidazole / dimethylformamide / 6 h / Ambient temperature

2: 92.9 percent / K₂CO₃ / methanol; H₂O / 48 h / Ambient temperature

3: 1.26 g / n-BuLi, Ph₃CH, p-TsCl, LiCl / diethyl ether; hexamethylphosphoric acid triamide; hexane / 0.42 h / 0 °C

4: n-BuLi, HMPA / tetrahydrofuran; hexane / 0.75 h / -70 °C

5: 50.2 percent / CaCO₃, NCS / H₂O; dimethylformamide / Ambient temperature

6: 57 percent / DBU / tetrahydrofuran / 6 h / Heating

7: 1) EtMgBr / 1) ether, room temp., 1 h. 10 min.; 2) ether evaporated; 100 degC, 10 min.

8: 71 percent / HF / acetonitrile; H₂O / 1 h / Ambient temperature

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; N-chloro-succinimide; n-butyllithium; triphenylmethane; hydrogen fluoride; ethylmagnesium bromide; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; p-toluenesulfonyl chloride; calcium carbonate; lithium chloride; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; hexane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0040-4020(01)96657-8

Reference yield:

(2E,6E,1'S*,4'S*)-7-(4'-hydroxy-3',3'-dimethyl-2'-oxacyclopentyl)-3,7-dimethyl-2,6-heptadienyl acetate (99477-55-1,99529-54-1,99529-56-3,99529-57-4) → (1''S,4''S)-(-)-ascofuranol (51759-79-6,99529-62-1)

Guidance literature:

Multi-step reaction with 10 steps

1: 5.14 g / 14 h / 80 °C

2: 76.3 percent / Et₃N, HSiCl₃ / benzene / 96 h / Ambient temperature

3: imidazole / dimethylformamide / 6 h / Ambient temperature

4: 92.9 percent / K₂CO₃ / methanol; H₂O / 48 h / Ambient temperature

5: 1.26 g / n-BuLi, Ph₃CH, p-TsCl, LiCl / diethyl ether; hexamethylphosphoric acid triamide; hexane / 0.42 h / 0 °C

6: n-BuLi, HMPA / tetrahydrofuran; hexane / 0.75 h / -70 °C

7: 50.2 percent / CaCO₃, NCS / H₂O; dimethylformamide / Ambient temperature

8: 57 percent / DBU / tetrahydrofuran / 6 h / Heating

9: 1) EtMgBr / 1) ether, room temp., 1 h. 10 min.; 2) ether evaporated; 100 degC, 10 min.

10: 71 percent / HF / acetonitrile; H₂O / 1 h / Ambient temperature

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; N-chloro-succinimide; n-butyllithium; triphenylmethane; trichlorosilane; hydrogen fluoride; ethylmagnesium bromide; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; p-toluenesulfonyl chloride; calcium carbonate; lithium chloride; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; hexane; water; N,N-dimethyl-formamide; acetonitrile; benzene;

DOI:10.1016/S0040-4020(01)96657-8

upstream raw materials:

(2'E,6'E,1''S,4''S)-5-chloro-2,4-dihydroxy-6-methyl-3-<7'-(4''-t-butyldimethylsilyloxy-3'',3''-dimethyl-2''-oxacyclopentyl)-3',7'-dimethyl-2',6'-heptadienyl>benzaldehyde

(2E,6E,1'S,4'S)-(+)-7-(4'-hydroxy-3',3'-dimethyl-2'-oxacyclopentyl)-3,7-dimethyl-2,6-heptadienyl acetate

(2E,6E,1'S*,4'S*)-7-(4'-hydroxy-3',3'-dimethyl-2'-oxacyclopentyl)-3,7-dimethyl-2,6-heptadienyl acetate

(2E,6E,1'S,4'S)-(+)-7-(4'-t-butyldimethylsilyloxy-3',3'-dimethyl-2'-oxacyclopentyl)-3,7-dimethyl-2,6-heptadien-1-ol

Downstream raw materials:

(1''S,4''S)-2,4-O-dimethylascofuranol

Ascofuranone

Refernces