3-[3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionic acid (R)-1-methyl-2-((R)-6-oxo-3,6-dihydro-2H-pyran-2-yl)-ethyl ester

Base Information

• Chemical Name: 3-[3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionic acid (R)-1-methyl-2-((R)-6-oxo-3,6-dihydro-2H-pyran-2-yl)-ethyl ester
• CAS No.: 116511-80-9
• Molecular Formula: C₂₉H₄₈O₆Si₂
• Molecular Weight: 548.868
• Mol file: 116511-80-9.mol

Synonyms:

Chemical Property of 3-[3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionic acid (R)-1-methyl-2-((R)-6-oxo-3,6-dihydro-2H-pyran-2-yl)-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-[3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionic acid (R)-1-methyl-2-((R)-6-oxo-3,6-dihydro-2H-pyran-2-yl)-ethyl ester

There total 9 articles about 3-[3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionic acid (R)-1-methyl-2-((R)-6-oxo-3,6-dihydro-2H-pyran-2-yl)-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: 27.0%

3,4-bis(O-tert-butyldimethylsilyl)-3,4-dihydroxyhydrocinnamic acid (116511-71-8) + (R)-4-Hydroxy-6-((R)-2-hydroxy-propyl)-tetrahydro-pyran-2-one (129987-26-4) → 3-[3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionic acid (S)-2-((S)-2-{3-[3,4-bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionyloxy}-propyl)-6-oxo-tetrahydro-pyran-4-yl ester (116511-79-6,129987-27-5) + 3-[3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionic acid (R)-1-methyl-2-((S)-6-oxo-3,6-dihydro-2H-pyran-2-yl)-ethyl ester (116511-80-9,131613-66-6)

Guidance literature:

With dmap; diethyl chlorophosphate; triethylamine; In acetonitrile;

DOI:10.1016/S0040-4039(00)96807-2

Reference yield:

((2S,6S)-2-Methoxy-6-methyl-4-oxo-tetrahydro-pyran-2-yl)-acetic acid tert-butyl ester (88559-60-8,96479-68-4,116561-88-7) → 3-[3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionic acid (R)-1-methyl-2-((S)-6-oxo-3,6-dihydro-2H-pyran-2-yl)-ethyl ester (116511-80-9,131613-66-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 17 percent / n-Bu₄NBH₄ / tetrahydrofuran; H₂O

2: 1.) HCl, 2.) NaBH₄ / 1.) THF, 2.) MeOH

3: 41 percent / CSA / benzene

4: 27 percent / (EtO)2POCl, Et₃N, DMAP / acetonitrile

With hydrogenchloride; dmap; sodium tetrahydroborate; camphor-10-sulfonic acid; tetrabutylammonium borohydride; diethyl chlorophosphate; triethylamine; In tetrahydrofuran; water; acetonitrile; benzene;

DOI:10.1016/S0040-4039(00)96807-2

Reference yield:

(5R,7S)-3,5,7-Trihydroxy-octanoic acid tert-butyl ester (116511-78-5) → 3-[3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionic acid (R)-1-methyl-2-((R)-6-oxo-3,6-dihydro-2H-pyran-2-yl)-ethyl ester (116511-80-9,131613-66-6)

Guidance literature:

Multi-step reaction with 2 steps

1: CSA / benzene

2: (EtO)2POCl, Et₃N, DMAP / acetonitrile

With dmap; camphor-10-sulfonic acid; diethyl chlorophosphate; triethylamine; In acetonitrile; benzene;

DOI:10.1016/S0040-4039(00)96807-2

upstream raw materials:

3,4-bis(O-tert-butyldimethylsilyl)-3,4-dihydroxyhydrocinnamic acid

(R)-4-Hydroxy-6-((R)-2-hydroxy-propyl)-tetrahydro-pyran-2-one

(5R,7R)-3,5,7-Trihydroxy-octanoic acid tert-butyl ester

((2S,4S,6S)-4-Hydroxy-2-methoxy-6-methyl-tetrahydro-pyran-2-yl)-acetic acid tert-butyl ester

Downstream raw materials:

3-(3,4-Dihydroxy-phenyl)-propionic acid (R)-1-methyl-2-((S)-6-oxo-3,6-dihydro-2H-pyran-2-yl)-ethyl ester