3-[3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionic acid (2R,4R)-2-((R)-2-{3-[3,4-bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionyloxy}-propyl)-6-oxo-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: 3-[3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionic acid (2R,4R)-2-((R)-2-{3-[3,4-bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionyloxy}-propyl)-6-oxo-tetrahydro-pyran-4-yl ester
• CAS No.: 129987-27-5
• Molecular Formula: C₅₀H₈₆O₁₀Si₄
• Molecular Weight: 959.569
• Mol file: 129987-27-5.mol

Synonyms:3-[3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionic acid (2R,4R)-2-((R)-2-{3-[3,4-bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionyloxy}-propyl)-6-oxo-tetrahydro-pyran-4-yl ester

Chemical Property of 3-[3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionic acid (2R,4R)-2-((R)-2-{3-[3,4-bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionyloxy}-propyl)-6-oxo-tetrahydro-pyran-4-yl 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 (2R,4R)-2-((R)-2-{3-[3,4-bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionyloxy}-propyl)-6-oxo-tetrahydro-pyran-4-yl ester

There total 24 articles about 3-[3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionic acid (2R,4R)-2-((R)-2-{3-[3,4-bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionyloxy}-propyl)-6-oxo-tetrahydro-pyran-4-yl 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: 95.0%

(3R,5R,7R)-3,5,7-trihydroxyoctanoic acid δ-lactone (129987-26-4) + 3,4-bis(O-tert-butyldimethylsilyl)-3,4-dihydroxyhydrocinnamic acid (116511-71-8) → 3-[3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionic acid (2R,4R)-2-((R)-2-{3-[3,4-bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionyloxy}-propyl)-6-oxo-tetrahydro-pyran-4-yl ester (129987-27-5)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; for 14h; Ambient temperature;

DOI:10.1248/cpb.38.2574

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 (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)

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: 35 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

upstream raw materials:

(3R,5R,7R)-3,5,7-trihydroxyoctanoic acid δ-lactone

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

methyl (3R,5R,7R)-3,5,7-trihydroxyoctanoate

Acetic acid (R)-2-[(2R,4S)-4-(2-hydroxy-ethyl)-1,5-dioxa-spiro[5.5]undec-2-yl]-1-methyl-ethyl 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

(R)-1-methyl-2-[(S)-6-oxo-3,6-dihydro-2H-pyran-2-yl]ethyl 3-(3,4-dihydroxyphenyl)propanoate

(-)-<5(S),7(R)>-7-<5-(oct-2-enolide)-3',4'-bis-(t-butyldimethylsilyloxy)>-dihydrocinnamate