4-[(1S,5S,7S,8R,10R,11S)-10-(4-Methoxy-benzyloxy)-8,14,14-trimethyl-3,9-dioxo-2,4-dioxa-tricyclo[9.2.1.0^1,5]tetradec-7-yl]-pent-4-enal

Base Information

• Chemical Name: 4-[(1S,5S,7S,8R,10R,11S)-10-(4-Methoxy-benzyloxy)-8,14,14-trimethyl-3,9-dioxo-2,4-dioxa-tricyclo[9.2.1.0^1,5]tetradec-7-yl]-pent-4-enal
• CAS No.: 350715-36-5
• Molecular Formula: C₂₈H₃₆O₇
• Molecular Weight: 484.59

Synonyms:4-[(1S,5S,7S,8R,10R,11S)-10-(4-Methoxy-benzyloxy)-8,14,14-trimethyl-3,9-dioxo-2,4-dioxa-tricyclo[9.2.1.0^1,5]tetradec-7-yl]-pent-4-enal

Chemical Property of 4-[(1S,5S,7S,8R,10R,11S)-10-(4-Methoxy-benzyloxy)-8,14,14-trimethyl-3,9-dioxo-2,4-dioxa-tricyclo[9.2.1.0^1,5]tetradec-7-yl]-pent-4-enal

Chemical Property:

Purity/Quality:

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Technology Process of 4-[(1S,5S,7S,8R,10R,11S)-10-(4-Methoxy-benzyloxy)-8,14,14-trimethyl-3,9-dioxo-2,4-dioxa-tricyclo[9.2.1.0^1,5]tetradec-7-yl]-pent-4-enal

There total 10 articles about 4-[(1S,5S,7S,8R,10R,11S)-10-(4-Methoxy-benzyloxy)-8,14,14-trimethyl-3,9-dioxo-2,4-dioxa-tricyclo[9.2.1.0^1,5]tetradec-7-yl]-pent-4-enal 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: 98.0%

(1S,5S,7S,8R,10R,11S)-7-(4-Hydroxy-1-methylene-butyl)-10-(4-methoxy-benzyloxy)-8,14,14-trimethyl-2,4-dioxa-tricyclo[9.2.1.01,5]tetradecane-3,9-dione → 4-[(1S,5S,7S,8R,10R,11S)-10-(4-Methoxy-benzyloxy)-8,14,14-trimethyl-3,9-dioxo-2,4-dioxa-tricyclo[9.2.1.01,5]tetradec-7-yl]-pent-4-enal (350715-36-5)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 - 20 ℃; for 2.33333h;

DOI:10.1021/jo020627v

Reference yield:

4-bromopent-4-en-1-ol (64180-78-5) → 4-[(1S,5S,7S,8R,10R,11S)-10-(4-Methoxy-benzyloxy)-8,14,14-trimethyl-3,9-dioxo-2,4-dioxa-tricyclo[9.2.1.01,5]tetradec-7-yl]-pent-4-enal (350715-36-5)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 15.74 g / Et₃N; DBU / CH₂Cl₂

2.1: tert-butyllithium / tetrahydrofuran; pentane / 0.5 h / -78 °C

2.2: 99 percent / tetrahydrofuran; pentane / 3 h / -78 °C

3.1: sodium hexamethyldisilazide / tetrahydrofuran / 0.33 h / 0 °C

3.2: 88 percent / tetrahydrofuran / -78 - -30 °C

4.1: tert-butyllithium / diethyl ether; pentane / 0.03 h / -78 °C

4.2: 96 percent / diethyl ether; pentane / 3.5 h / -78 - 0 °C

5.1: potassium hexamethyldisilazide; 18-crown-6 / tetrahydrofuran; toluene / 1.48 h / -78 - -40 °C

5.2: 81 percent / tetrahydrofuran; toluene / 3 h / -78 °C

6.1: 54 percent / NMO*H₂O; osmium tetraoxide; water / acetone / 120 h / 0 °C

7.1: pyridine / CH₂Cl₂; toluene / 0.25 h / -78 °C

8.1: 890 mg / methanol; Dowex 50X₄-400 / 2.5 h

9.1: 98 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 2.33 h / -78 - 20 °C

With pyridine; methanol; osmium(VIII) oxide; oxalyl dichloride; 18-crown-6 ether; Dowex 50X₄-400; water; tert.-butyl lithium; sodium hexamethyldisilazane; potassium hexamethylsilazane; dimethyl sulfoxide; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; acetone; toluene; pentane; 3.2: Wittig condensation / 9.1: Swern oxidation;

DOI:10.1021/jo020627v

Reference yield:

((4-bromopent-4-en-1-yl)oxy)(tert-butyl)dimethylsilane (120001-35-6) → 4-[(1S,5S,7S,8R,10R,11S)-10-(4-Methoxy-benzyloxy)-8,14,14-trimethyl-3,9-dioxo-2,4-dioxa-tricyclo[9.2.1.01,5]tetradec-7-yl]-pent-4-enal (350715-36-5)

Guidance literature:

Multi-step reaction with 8 steps

1.1: tert-butyllithium / tetrahydrofuran; pentane / 0.5 h / -78 °C

1.2: 99 percent / tetrahydrofuran; pentane / 3 h / -78 °C

2.1: sodium hexamethyldisilazide / tetrahydrofuran / 0.33 h / 0 °C

2.2: 88 percent / tetrahydrofuran / -78 - -30 °C

3.1: tert-butyllithium / diethyl ether; pentane / 0.03 h / -78 °C

3.2: 96 percent / diethyl ether; pentane / 3.5 h / -78 - 0 °C

4.1: potassium hexamethyldisilazide; 18-crown-6 / tetrahydrofuran; toluene / 1.48 h / -78 - -40 °C

4.2: 81 percent / tetrahydrofuran; toluene / 3 h / -78 °C

5.1: 54 percent / NMO*H₂O; osmium tetraoxide; water / acetone / 120 h / 0 °C

6.1: pyridine / CH₂Cl₂; toluene / 0.25 h / -78 °C

7.1: 890 mg / methanol; Dowex 50X₄-400 / 2.5 h

8.1: 98 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 2.33 h / -78 - 20 °C

With pyridine; methanol; osmium(VIII) oxide; oxalyl dichloride; 18-crown-6 ether; Dowex 50X₄-400; water; tert.-butyl lithium; sodium hexamethyldisilazane; potassium hexamethylsilazane; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; acetone; toluene; pentane; 2.2: Wittig condensation / 8.1: Swern oxidation;

DOI:10.1021/jo020627v

upstream raw materials:

4-bromopent-4-en-1-ol

((4-bromopent-4-en-1-yl)oxy)(tert-butyl)dimethylsilane

4-bromo-4-pentenoic acid tert-butyl ester

5-(tert-butyldimethylsilyloxy)-2-methylenepentanal

Downstream raw materials:

(1S,4R,8S,9R,10R,11R,12S)-8-(tert-Butyl-dimethyl-silanyloxy)-1,10-dihydroxy-11-(4-methoxy-benzyloxy)-9,15,15-trimethyl-5-methylene-tricyclo[10.2.1.0^4,9]pentadecan-2-one

(1S,2R,4S,5S,9R,11S,12S)-5-(tert-Butyl-dimethyl-silanyloxy)-11,12-dihydroxy-2-(4-methoxy-benzyloxy)-4,15,15-trimethyl-8-methylene-tricyclo[10.2.1.0^4,9]pentadecan-3-one

C₄₁H₄₄O₉

C₃₅H₄₄O₈

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