Benzoic acid 2-[(1R,2S,6R,7S,8S)-2,7-dihydroxy-8-methyl-10-oxo-5,9-dioxa-tricyclo[6.2.1.0^2,6]undec-(3E)-ylidene]-ethyl ester

Base Information

• Chemical Name: Benzoic acid 2-[(1R,2S,6R,7S,8S)-2,7-dihydroxy-8-methyl-10-oxo-5,9-dioxa-tricyclo[6.2.1.0^2,6]undec-(3E)-ylidene]-ethyl ester
• CAS No.: 114158-48-4
• Molecular Formula: C₁₉H₂₀O₇
• Molecular Weight: 360.364
• Mol file: 114158-48-4.mol

Synonyms:Benzoic acid 2-[(1R,2S,6R,7S,8S)-2,7-dihydroxy-8-methyl-10-oxo-5,9-dioxa-tricyclo[6.2.1.0^2,6]undec-(3E)-ylidene]-ethyl ester

Chemical Property of Benzoic acid 2-[(1R,2S,6R,7S,8S)-2,7-dihydroxy-8-methyl-10-oxo-5,9-dioxa-tricyclo[6.2.1.0^2,6]undec-(3E)-ylidene]-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid 2-[(1R,2S,6R,7S,8S)-2,7-dihydroxy-8-methyl-10-oxo-5,9-dioxa-tricyclo[6.2.1.0^2,6]undec-(3E)-ylidene]-ethyl ester

There total 15 articles about Benzoic acid 2-[(1R,2S,6R,7S,8S)-2,7-dihydroxy-8-methyl-10-oxo-5,9-dioxa-tricyclo[6.2.1.0^2,6]undec-(3E)-ylidene]-ethyl ester 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: 82.0%

Benzoic acid (E)-4-methanesulfonyloxy-3-((1S,2S,6R,7S,8R)-7-methoxymethoxy-1,4,4-trimethyl-9-oxo-3,5,10-trioxa-tricyclo[6.2.1.02,6]undec-7-yl)-but-2-enyl ester (114158-47-3) → Benzoic acid 2-[(1R,2S,6R,7S,8S)-2,7-dihydroxy-8-methyl-10-oxo-5,9-dioxa-tricyclo[6.2.1.02,6]undec-(3E)-ylidene]-ethyl ester (114158-48-4)

Guidance literature:

With Dowex 50W-X₈; In tetrahydrofuran; water; at 70 ℃;

DOI:10.1021/jo00244a063

Reference yield:

(1S)-1-[(4R,5R)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]ethan-1-ol (93223-61-1,114296-87-6,117557-98-9,124990-87-0) → Benzoic acid 2-[(1R,2S,6R,7S,8S)-2,7-dihydroxy-8-methyl-10-oxo-5,9-dioxa-tricyclo[6.2.1.02,6]undec-(3E)-ylidene]-ethyl ester (114158-48-4)

Guidance literature:

Multi-step reaction with 15 steps

1: 99 percent / imidazole / dimethylformamide / -30 °C

2: 95 percent / pyridinium chlorochromate on neutral Al₂O₃ / CH₂Cl₂ / 22 °C

3: 95 percent / tetrahydrofuran / -78 °C

4: 1.) O₃, 2.) Ph₃P / 1.) in CH₂Cl₂, -78 deg C

5: 89 percent / pyridinium chlorochromate on neutral Al₂O₃ / CH₂Cl₂ / 22 °C

6: 98 percent / 1.0 M n-Bu₄NF / tetrahydrofuran / 0 °C

7: 88 percent / pyridinium chlorochromate on neutral Al₂O₃, NaOAc / CH₂Cl₂ / 22 °C

8: 87 percent / 1.) 1.3 M sec-BuLi, 2.) MgBr₂*Et₂O / 1.) in Et₂O, -78 deg C, 2.) heating to -40 deg C

9: 1.) ClCOCOCl, 2.) Et₃N / 1.) in CH₂Cl₂/DMSO, -78 deg C, 2.) warmed to -20 deg C

10: LDA / tetrahydrofuran / -78 °C

11: 82 percent / sodium hydride / 0 °C

12: 1.) N-bromosuccinimide, 2.) sodium borohydride / 1.) in THF/H₂O (1:4), 0 deg C

13: 82 percent / Et₃N, 4-DMAP / -78 - -40 °C

14: 90 percent / Et₃N / CH₂Cl₂ / 0 °C

15: 82 percent / Dowex 50W-X₈ / tetrahydrofuran; H₂O / 70 °C

With 1H-imidazole; dmap; sodium tetrahydroborate; N-Bromosuccinimide; oxalyl dichloride; pyridiniumchlorochromate on aluminumoxide; Dowex 50W-X₈; tetrabutyl ammonium fluoride; sec.-butyllithium; sodium acetate; sodium hydride; ozone; triethylamine; triphenylphosphine; magnesium bromide; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jo00244a063

Reference yield:

(S)-5-((4S,5S)-5-Hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-methyl-dihydro-furan-2-one (114158-36-0) → Benzoic acid 2-[(1R,2S,6R,7S,8S)-2,7-dihydroxy-8-methyl-10-oxo-5,9-dioxa-tricyclo[6.2.1.02,6]undec-(3E)-ylidene]-ethyl ester (114158-48-4)

Guidance literature:

Multi-step reaction with 9 steps

1: 88 percent / pyridinium chlorochromate on neutral Al₂O₃, NaOAc / CH₂Cl₂ / 22 °C

2: 87 percent / 1.) 1.3 M sec-BuLi, 2.) MgBr₂*Et₂O / 1.) in Et₂O, -78 deg C, 2.) heating to -40 deg C

3: 1.) ClCOCOCl, 2.) Et₃N / 1.) in CH₂Cl₂/DMSO, -78 deg C, 2.) warmed to -20 deg C

4: LDA / tetrahydrofuran / -78 °C

5: 82 percent / sodium hydride / 0 °C

6: 1.) N-bromosuccinimide, 2.) sodium borohydride / 1.) in THF/H₂O (1:4), 0 deg C

7: 82 percent / Et₃N, 4-DMAP / -78 - -40 °C

8: 90 percent / Et₃N / CH₂Cl₂ / 0 °C

9: 82 percent / Dowex 50W-X₈ / tetrahydrofuran; H₂O / 70 °C

With dmap; sodium tetrahydroborate; N-Bromosuccinimide; oxalyl dichloride; pyridiniumchlorochromate on aluminumoxide; Dowex 50W-X₈; sec.-butyllithium; sodium acetate; sodium hydride; triethylamine; magnesium bromide; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; water;

DOI:10.1021/jo00244a063

upstream raw materials:

Benzoic acid (E)-4-methanesulfonyloxy-3-((1S,2S,6R,7S,8R)-7-methoxymethoxy-1,4,4-trimethyl-9-oxo-3,5,10-trioxa-tricyclo[6.2.1.0^2,6]undec-7-yl)-but-2-enyl ester

(1S)-1-[(4R,5R)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]ethan-1-ol

(S)-5-((4S,5S)-5-Hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-methyl-dihydro-furan-2-one

(4R,5S)-2,2-Dimethyl-5-((S)-2-methyl-5-oxo-tetrahydro-furan-2-yl)-[1,3]dioxolane-4-carbaldehyde

Downstream raw materials:

Benzoic acid 2-[(1R,2S,6R,7S,8S)-2,7-bis-methoxymethoxy-8-methyl-10-oxo-5,9-dioxa-tricyclo[6.2.1.0^2,6]undec-(3E)-ylidene]-ethyl ester