(2R,6S)-2-{(4R,6S)-6-[(S)-1-(4-Methoxy-benzyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-6-methyl-oct-7-en-2-ol

Base Information

• Chemical Name: (2R,6S)-2-{(4R,6S)-6-[(S)-1-(4-Methoxy-benzyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-6-methyl-oct-7-en-2-ol
• CAS No.: 355387-00-7
• Molecular Formula: C₂₅H₄₀O₅
• Molecular Weight: 420.59

Synonyms:(2R,6S)-2-{(4R,6S)-6-[(S)-1-(4-Methoxy-benzyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-6-methyl-oct-7-en-2-ol

Chemical Property of (2R,6S)-2-{(4R,6S)-6-[(S)-1-(4-Methoxy-benzyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-6-methyl-oct-7-en-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,6S)-2-{(4R,6S)-6-[(S)-1-(4-Methoxy-benzyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-6-methyl-oct-7-en-2-ol

There total 7 articles about (2R,6S)-2-{(4R,6S)-6-[(S)-1-(4-Methoxy-benzyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-6-methyl-oct-7-en-2-ol 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: 78.0%

(S)-(+)-4-methylhex-5-enyl bromide (69274-87-9) + 1-{(4R,6S)-6-[(S)-1-(4-Methoxy-benzyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethanone (355386-98-0) → (2R,6S)-2-{(4R,6S)-6-[(S)-1-(4-Methoxy-benzyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-6-methyl-oct-7-en-2-ol (355387-00-7) + (2S,6S)-2-{(4R,6S)-6-[(S)-1-(4-Methoxy-benzyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-6-methyl-oct-7-en-2-ol

Guidance literature:

(S)-(+)-4-methylhex-5-enyl bromide; With magnesium; In tetrahydrofuran; at 25 ℃; for 0.5h;

1-{(4R,6S)-6-[(S)-1-(4-Methoxy-benzyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethanone; With magnesium bromide; In tetrahydrofuran; dichloromethane; at -78 ℃; for 0.5h;

In tetrahydrofuran; dichloromethane; at -78 - 25 ℃; for 2h;

DOI:10.1002/1521-3765(20010518)7:10<2261::AID-CHEM2261>3.0.CO;2-F

Reference yield:

(4S,5S)-4-hydroxy-5-(4-methoxybenzyloxy)-1-hexene (214892-50-9) → (2R,6S)-2-{(4R,6S)-6-[(S)-1-(4-Methoxy-benzyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-6-methyl-oct-7-en-2-ol (355387-00-7)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 97 percent / imidazole / dimethylformamide / 16 h / 22 °C

2.1: O₃ / methanol; CH₂Cl₂ / -78 °C

2.2: 98 percent / PPh₃ / methanol; CH₂Cl₂ / -78 - 25 °C

3.1: 89 percent / tetrahydrofuran / 0.75 h / -10 °C

4.1: 99 percent / TBAF / tetrahydrofuran / 1 h / 25 °C

5.1: 99 percent / p-TsOH*H₂O / 3 h / 25 °C

6.1: O₃ / methanol; CH₂Cl₂ / 0.25 h / -78 °C

6.2: PPh₃ / methanol; CH₂Cl₂ / 12 h / 25 °C

6.3: 94 percent / K₂CO₃ / methanol / 1 h / 25 °C

7.1: Mg / tetrahydrofuran / 0.5 h / 25 °C

7.2: MgBr₂*Et₂O / CH₂Cl₂; tetrahydrofuran / 0.5 h / -78 °C

7.3: 78 percent / CH₂Cl₂; tetrahydrofuran / 2 h / -78 - 25 °C

With 1H-imidazole; tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; ozone; magnesium; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 3.1: Grignard reaction / 7.3: Grignard reaction;

DOI:10.1002/1521-3765(20010518)7:10<2261::AID-CHEM2261>3.0.CO;2-F

Reference yield:

(3S,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-pentanal (263761-21-3) → (2R,6S)-2-{(4R,6S)-6-[(S)-1-(4-Methoxy-benzyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-6-methyl-oct-7-en-2-ol (355387-00-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 89 percent / tetrahydrofuran / 0.75 h / -10 °C

2.1: 99 percent / TBAF / tetrahydrofuran / 1 h / 25 °C

3.1: 99 percent / p-TsOH*H₂O / 3 h / 25 °C

4.1: O₃ / methanol; CH₂Cl₂ / 0.25 h / -78 °C

4.2: PPh₃ / methanol; CH₂Cl₂ / 12 h / 25 °C

4.3: 94 percent / K₂CO₃ / methanol / 1 h / 25 °C

5.1: Mg / tetrahydrofuran / 0.5 h / 25 °C

5.2: MgBr₂*Et₂O / CH₂Cl₂; tetrahydrofuran / 0.5 h / -78 °C

5.3: 78 percent / CH₂Cl₂; tetrahydrofuran / 2 h / -78 - 25 °C

With tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; ozone; magnesium; In tetrahydrofuran; methanol; dichloromethane; 1.1: Grignard reaction / 5.3: Grignard reaction;

DOI:10.1002/1521-3765(20010518)7:10<2261::AID-CHEM2261>3.0.CO;2-F

upstream raw materials:

(S)-(+)-4-methylhex-5-enyl bromide

1-{(4R,6S)-6-[(S)-1-(4-Methoxy-benzyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethanone

(4S,5S)-4-hydroxy-5-(4-methoxybenzyloxy)-1-hexene

(3S,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-pentanal

Downstream raw materials:

epothilone B

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