3-(4-Benzyloxy-3-{4-[(1R,2R)-1,2-bis-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-propyl]-phenoxy}-phenyl)-propionic acid

Base Information

• Chemical Name: 3-(4-Benzyloxy-3-{4-[(1R,2R)-1,2-bis-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-propyl]-phenoxy}-phenyl)-propionic acid
• CAS No.: 202645-46-3
• Molecular Formula: C₃₇H₅₄O₇Si₂
• Molecular Weight: 667.003

Synonyms:3-(4-Benzyloxy-3-{4-[(1R,2R)-1,2-bis-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-propyl]-phenoxy}-phenyl)-propionic acid

Chemical Property of 3-(4-Benzyloxy-3-{4-[(1R,2R)-1,2-bis-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-propyl]-phenoxy}-phenyl)-propionic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-(4-Benzyloxy-3-{4-[(1R,2R)-1,2-bis-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-propyl]-phenoxy}-phenyl)-propionic acid

There total 17 articles about 3-(4-Benzyloxy-3-{4-[(1R,2R)-1,2-bis-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-propyl]-phenoxy}-phenyl)-propionic acid 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: 90.0%

2,2-Dimethyl-propionic acid (2R,3R)-3-{4-[2-benzyloxy-5-(2-carboxy-ethyl)-phenoxy]-phenyl}-2,3-bis-(tert-butyl-dimethyl-silanyloxy)-propyl ester (172919-13-0) → 3-(4-Benzyloxy-3-{4-[(1R,2R)-1,2-bis-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-propyl]-phenoxy}-phenyl)-propionic acid (202645-46-3)

Guidance literature:

With diisobutylaluminium hydride; In dichloromethane; cyclohexane; at -78 ℃; for 0.166667h;

DOI:10.1002/(SICI)1521-3765(199801)4:1<33::AID-CHEM33>3.0.CO;2-8

Reference yield:

4-benzyloxy-3-hydroxy-benzaldehyde (4049-39-2) → 3-(4-Benzyloxy-3-{4-[(1R,2R)-1,2-bis-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-propyl]-phenoxy}-phenyl)-propionic acid (202645-46-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 93 percent / benzene / 2 h / 25 °C

2: 97 percent / H₂ / 5percent Pd/C / benzene / 5 h / 25 °C

3: 78 percent / K₂CO₃, CuBr*Me₂S / pyridine / 6 h / 140 °C

4: 87 percent / K₃Fe(CN)6, K₂CO₃, (DHQD)2PHAL, K₂Os₂(OH)4, CH₃SO₂NH₂ / 2-methyl-propan-2-ol; H₂O / 12 h / 0 °C

5: 97 percent / imidazole / dimethylformamide / 3 h / 25 °C

6: 94 percent / aq. LiOH / tetrahydrofuran; methanol / 2 h / 0 - 25 °C

7: 90 percent / DIBAL-H / CH₂Cl₂; cyclohexane / 0.17 h / -78 °C

With 1H-imidazole; potassium osmate; lithium hydroxide; copper(I) bromide dimethylsulfide complex; methanesulfonamide; hydrogen; diisobutylaluminium hydride; potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; potassium hexacyanoferrate(III); palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; dichloromethane; cyclohexane; water; N,N-dimethyl-formamide; tert-butyl alcohol; benzene;

DOI:10.1002/(SICI)1521-3765(199801)4:1<33::AID-CHEM33>3.0.CO;2-8

Reference yield:

benzyl bromide (100-39-0) → 3-(4-Benzyloxy-3-{4-[(1R,2R)-1,2-bis-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-propyl]-phenoxy}-phenyl)-propionic acid (202645-46-3)

Guidance literature:

Multi-step reaction with 8 steps

1: 76 percent / K₂CO₃ / dimethylformamide / 1.) 60 deg C, 4 h, 2.) 25 deg C, 12 h

2: 93 percent / benzene / 2 h / 25 °C

3: 97 percent / H₂ / 5percent Pd/C / benzene / 5 h / 25 °C

4: 78 percent / K₂CO₃, CuBr*Me₂S / pyridine / 6 h / 140 °C

5: 87 percent / K₃Fe(CN)6, K₂CO₃, (DHQD)2PHAL, K₂Os₂(OH)4, CH₃SO₂NH₂ / 2-methyl-propan-2-ol; H₂O / 12 h / 0 °C

6: 97 percent / imidazole / dimethylformamide / 3 h / 25 °C

7: 94 percent / aq. LiOH / tetrahydrofuran; methanol / 2 h / 0 - 25 °C

8: 90 percent / DIBAL-H / CH₂Cl₂; cyclohexane / 0.17 h / -78 °C

With 1H-imidazole; potassium osmate; lithium hydroxide; copper(I) bromide dimethylsulfide complex; methanesulfonamide; hydrogen; diisobutylaluminium hydride; potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; potassium hexacyanoferrate(III); palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; dichloromethane; cyclohexane; water; N,N-dimethyl-formamide; tert-butyl alcohol; benzene;

DOI:10.1002/(SICI)1521-3765(199801)4:1<33::AID-CHEM33>3.0.CO;2-8

upstream raw materials:

2,2-Dimethyl-propionic acid (2R,3R)-3-{4-[2-benzyloxy-5-(2-ethoxycarbonyl-ethyl)-phenoxy]-phenyl}-2,3-bis-(tert-butyl-dimethyl-silanyloxy)-propyl ester

2,2-Dimethyl-propionic acid (2R,3R)-3-{4-[2-benzyloxy-5-(2-carboxy-ethyl)-phenoxy]-phenyl}-2,3-bis-(tert-butyl-dimethyl-silanyloxy)-propyl ester

4-benzyloxy-3-hydroxy-benzaldehyde

ethyl (E)-3-(4-bromophenyl)-2-propenoate

Downstream raw materials:

(13R,14R)-4-Benzyloxy-13,14-bis-(tert-butyl-dimethyl-silanyloxy)-2,11-dioxa-tricyclo[13.2.2.1^3,7]icosa-1⁽¹⁸⁾,3,5,7⁽²⁰⁾,15⁽¹⁹⁾,16-hexaen-10-one

combretastatin D-2

(13R,14R)-4-benzyloxy-13,14-dihydroxy-2,11-dioxatricyclo[13.2.2.1^3,7]eicosa-1⁽¹⁸⁾,3,5,7⁽²⁰⁾,1⁽¹⁹⁾,16-hexaen-10-one

combretastatin D-2 benzyl ether

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