3-chloro-4,6-dihydroxy-5-{(2E,6E)-7-[(2S,4S)-4-hydroxy-5,5-dimethyltetrahydrofuran-2-yl]-3-methylocta-2,6-dien-1-yl}-2-methylbenzaldehyde

Base Information

• Chemical Name: 3-chloro-4,6-dihydroxy-5-{(2E,6E)-7-[(2S,4S)-4-hydroxy-5,5-dimethyltetrahydrofuran-2-yl]-3-methylocta-2,6-dien-1-yl}-2-methylbenzaldehyde
• CAS No.: 99529-62-1
• Molecular Formula: C₂₃H₃₁ClO₅
• Molecular Weight: 422.949
• Mol file: 99529-62-1.mol

Synonyms:

Chemical Property of 3-chloro-4,6-dihydroxy-5-{(2E,6E)-7-[(2S,4S)-4-hydroxy-5,5-dimethyltetrahydrofuran-2-yl]-3-methylocta-2,6-dien-1-yl}-2-methylbenzaldehyde

Chemical Property:

• Vapor Pressure: 1.03E-14mmHg at 25°C
• Boiling Point: 588.9°Cat760mmHg
• Flash Point: 310°C
• Density: 1.211g/cm³

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-chloro-4,6-dihydroxy-5-{(2E,6E)-7-[(2S,4S)-4-hydroxy-5,5-dimethyltetrahydrofuran-2-yl]-3-methylocta-2,6-dien-1-yl}-2-methylbenzaldehyde

There total 20 articles about 3-chloro-4,6-dihydroxy-5-{(2E,6E)-7-[(2S,4S)-4-hydroxy-5,5-dimethyltetrahydrofuran-2-yl]-3-methylocta-2,6-dien-1-yl}-2-methylbenzaldehyde 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: 70.0%

(2'E,6'E,1''R,4''R)-5-chloro-2,4-dihydroxy-6-methyl-3-<7'-(4''-t-butyldimethylsilyloxy-3'',3''-dimethyl-2''-oxacyclopentyl)-3',7'-dimethyl-2',6'-heptadienyl>benzaldehyde (99529-61-0) → (1''R,4''R)-(+)-ascofuranol (99529-63-2,99529-62-1)

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

upstream raw materials:

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

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

Refernces