2,2-Dimethyl-propionic acid (2R,4R,5R)-7-benzyloxy-4-hydroxy-2-methyl-5-triisopropylsilanyloxy-heptyl ester

Base Information

• Chemical Name: 2,2-Dimethyl-propionic acid (2R,4R,5R)-7-benzyloxy-4-hydroxy-2-methyl-5-triisopropylsilanyloxy-heptyl ester
• CAS No.: 795306-65-9
• Molecular Formula: C₂₉H₅₂O₅Si
• Molecular Weight: 508.814
• Mol file: 795306-65-9.mol

Synonyms:2,2-Dimethyl-propionic acid (2R,4R,5R)-7-benzyloxy-4-hydroxy-2-methyl-5-triisopropylsilanyloxy-heptyl ester

Chemical Property of 2,2-Dimethyl-propionic acid (2R,4R,5R)-7-benzyloxy-4-hydroxy-2-methyl-5-triisopropylsilanyloxy-heptyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,2-Dimethyl-propionic acid (2R,4R,5R)-7-benzyloxy-4-hydroxy-2-methyl-5-triisopropylsilanyloxy-heptyl ester

There total 11 articles about 2,2-Dimethyl-propionic acid (2R,4R,5R)-7-benzyloxy-4-hydroxy-2-methyl-5-triisopropylsilanyloxy-heptyl 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: 82.0%

(2R,4R,5R)-7-Benzyloxy-2-methyl-5-triisopropylsilanyloxy-heptane-1,4-diol (795306-64-8) + pivaloyl chloride (3282-30-2) → 2,2-Dimethyl-propionic acid (2R,4R,5R)-7-benzyloxy-4-hydroxy-2-methyl-5-triisopropylsilanyloxy-heptyl ester (795306-65-9)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at -78 - 20 ℃; for 2.75h;

DOI:10.1039/b410092a

Reference yield:

(R)-5-(3-Benzyloxy-1-hydroxy-propyl)-3-methyl-dihydro-furan-2-one → 2,2-Dimethyl-propionic acid (2R,4R,5R)-7-benzyloxy-4-hydroxy-2-methyl-5-triisopropylsilanyloxy-heptyl ester (795306-65-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 88 percent / imidazole; DMAP / dimethylformamide / 18 h / 20 °C

2: 99 percent / LiBH₄; MeOH / tetrahydrofuran / 4 h / 0 °C

3: 82 percent / DMAP; Et₃N / CH₂Cl₂ / 2.75 h / -78 - 20 °C

With 1H-imidazole; methanol; dmap; lithium borohydride; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1039/b410092a

Reference yield:

(3R,5R)-5-((R)-3-Benzyloxy-1-triisopropylsilanyloxy-propyl)-3-methyl-dihydro-furan-2-one (795306-62-6) → 2,2-Dimethyl-propionic acid (2R,4R,5R)-7-benzyloxy-4-hydroxy-2-methyl-5-triisopropylsilanyloxy-heptyl ester (795306-65-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 99 percent / LiBH₄; MeOH / tetrahydrofuran / 4 h / 0 °C

2: 82 percent / DMAP; Et₃N / CH₂Cl₂ / 2.75 h / -78 - 20 °C

With methanol; dmap; lithium borohydride; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1039/b410092a

upstream raw materials:

(2R,4R,5R)-7-Benzyloxy-2-methyl-5-triisopropylsilanyloxy-heptane-1,4-diol

pivaloyl chloride

(3R,5R)-5-((R)-3-Benzyloxy-1-triisopropylsilanyloxy-propyl)-3-methyl-dihydro-furan-2-one

(S)-4-Benzyl-3-((E)-(R)-7-benzyloxy-2-methyl-hept-4-enoyl)-oxazolidin-2-one

Downstream raw materials:

(4R,6R,7R)-2-Benzenesulfonyl-6,9-bis-benzyloxy-1-{(2S,6S)-6-[(E)-5-(tert-butyl-diphenyl-silanyloxy)-pent-1-enyl]-2-methoxy-5,6-dihydro-2H-pyran-2-yl}-4-methyl-7-triethylsilanyloxy-nonan-3-one

C₅₂H₇₇BrO₇Si₂

(4R,6R,7R)-6,9-Bis-benzyloxy-1-{(2S,6S)-6-[(E)-5-(tert-butyl-diphenyl-silanyloxy)-pent-1-enyl]-2-methoxy-5,6-dihydro-2H-pyran-2-yl}-4-methyl-7-triethylsilanyloxy-nonan-3-one

{(E)-5-[(2S,6R,8R,10R,11R,13R)-11-Benzyloxy-10-(2-benzyloxy-ethyl)-13-methyl-1,7,9-trioxa-dispiro[5.1.5.2]pentadec-4-en-2-yl]-pent-4-enyloxy}-tert-butyl-diphenyl-silane