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

Base Information

• Chemical Name: 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
• CAS No.: 172919-13-0
• Molecular Formula: C₄₂H₆₂O₈Si₂
• Molecular Weight: 751.12

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 12 articles about 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 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: 94.0%

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 (172919-09-4) → 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)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; methanol; at 0 - 25 ℃; for 2h;

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) → 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)

Guidance literature:

Multi-step reaction with 6 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

With 1H-imidazole; potassium osmate; lithium hydroxide; copper(I) bromide dimethylsulfide complex; methanesulfonamide; hydrogen; potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; potassium hexacyanoferrate(III); palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; 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) → 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)

Guidance literature:

Multi-step reaction with 7 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

With 1H-imidazole; potassium osmate; lithium hydroxide; copper(I) bromide dimethylsulfide complex; methanesulfonamide; hydrogen; potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; potassium hexacyanoferrate(III); palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; 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

4-benzyloxy-3-hydroxy-benzaldehyde

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

(2E)-3-(4-bromophenyl)prop-2-en-1-ol

Downstream raw materials:

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

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

(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

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