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

Base Information

• Chemical Name: (2'E,6'E,1''S,4''S)-4-chloro-2-<7'-(4''-t-butyldimethylsilyloxy-3'',3''-dimethyl-2''-oxacyclopentyl)-3',7'-dimethyl-2',6'-heptadienyl>orcinol
• CAS No.: 99477-62-0
• Molecular Formula: C₂₈H₄₅ClO₄Si
• Molecular Weight: 509.201

Synonyms:(2'E,6'E,1''S,4''S)-4-chloro-2-<7'-(4''-t-butyldimethylsilyloxy-3'',3''-dimethyl-2''-oxacyclopentyl)-3',7'-dimethyl-2',6'-heptadienyl>orcinol

Chemical Property of (2'E,6'E,1''S,4''S)-4-chloro-2-<7'-(4''-t-butyldimethylsilyloxy-3'',3''-dimethyl-2''-oxacyclopentyl)-3',7'-dimethyl-2',6'-heptadienyl>orcinol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of (2'E,6'E,1''S,4''S)-4-chloro-2-<7'-(4''-t-butyldimethylsilyloxy-3'',3''-dimethyl-2''-oxacyclopentyl)-3',7'-dimethyl-2',6'-heptadienyl>orcinol

There total 9 articles about (2'E,6'E,1''S,4''S)-4-chloro-2-<7'-(4''-t-butyldimethylsilyloxy-3'',3''-dimethyl-2''-oxacyclopentyl)-3',7'-dimethyl-2',6'-heptadienyl>orcinol 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: 57.0%

(2'E,6'E,1''S,4''S)-3-<7'-(4''-t-butyldimethylsilyloxy-3'',3''-dimethyl-2''-oxacyclopentyl)-3',7'-dimethyl-2',6'-heptadienyl>-1,5-dichloro-6-methyl-2,4-cyclohexanedione (99477-61-9) → (2'E,6'E,1''S,4''S)-4-chloro-2-<7'-(4''-t-butyldimethylsilyloxy-3'',3''-dimethyl-2''-oxacyclopentyl)-3',7'-dimethyl-2',6'-heptadienyl>orcinol (99477-62-0)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; for 6h; Heating;

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) → (2'E,6'E,1''S,4''S)-4-chloro-2-<7'-(4''-t-butyldimethylsilyloxy-3'',3''-dimethyl-2''-oxacyclopentyl)-3',7'-dimethyl-2',6'-heptadienyl>orcinol (99477-62-0)

Guidance literature:

Multi-step reaction with 6 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

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; N-chloro-succinimide; n-butyllithium; triphenylmethane; 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;

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

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (2'E,6'E,1''S,4''S)-4-chloro-2-<7'-(4''-t-butyldimethylsilyloxy-3'',3''-dimethyl-2''-oxacyclopentyl)-3',7'-dimethyl-2',6'-heptadienyl>orcinol (99477-62-0)

Guidance literature:

Multi-step reaction with 6 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

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; N-chloro-succinimide; n-butyllithium; triphenylmethane; 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;

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

upstream raw materials:

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

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

tert-butyldimethylsilyl chloride

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

Downstream raw materials:

(1''S,4''S)-(-)-ascofuranol

Ascofuranone

(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

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