2,2,2-trichloroethyl (4R,5S,9R)-4-benzyloxy-9-tert-butyldimethylsiloxy-5-methyl-7-oxo-6-oxadec-(2E)-enoate

Base Information

• Chemical Name: 2,2,2-trichloroethyl (4R,5S,9R)-4-benzyloxy-9-tert-butyldimethylsiloxy-5-methyl-7-oxo-6-oxadec-(2E)-enoate
• CAS No.: 455934-76-6
• Molecular Formula: C₂₅H₃₇Cl₃O₆Si
• Molecular Weight: 568.01
• Mol file: 455934-76-6.mol

Synonyms:2,2,2-trichloroethyl (4R,5S,9R)-4-benzyloxy-9-tert-butyldimethylsiloxy-5-methyl-7-oxo-6-oxadec-(2E)-enoate

Chemical Property of 2,2,2-trichloroethyl (4R,5S,9R)-4-benzyloxy-9-tert-butyldimethylsiloxy-5-methyl-7-oxo-6-oxadec-(2E)-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,2,2-trichloroethyl (4R,5S,9R)-4-benzyloxy-9-tert-butyldimethylsiloxy-5-methyl-7-oxo-6-oxadec-(2E)-enoate

There total 1 articles about 2,2,2-trichloroethyl (4R,5S,9R)-4-benzyloxy-9-tert-butyldimethylsiloxy-5-methyl-7-oxo-6-oxadec-(2E)-enoate 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%

3-(R)-t-butyldimethylsilyloxybutanoic acid (105729-41-7,107493-76-5,101515-46-2) + 2,2,2-trichloroethyl (4R,5S)-4-benzyloxy-5-hydroxy-2(E)-hexenoate (294198-50-8) → 2,2,2-trichloroethyl (4R,5S,9R)-4-benzyloxy-9-tert-butyldimethylsiloxy-5-methyl-7-oxo-6-oxadec-(2E)-enoate (455934-76-6)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1016/S0957-4166(02)00180-5

Reference yield: 93.0%

2,2,2-trichloroethyl (4R,5S,9R)-4-benzyloxy-9-tert-butyldimethylsiloxy-5-methyl-7-oxo-6-oxadec-(2E)-enoate (455934-76-6) → (E)-(4R,5S)-4-Benzyloxy-5-((R)-3-hydroxy-butyryloxy)-hex-2-enoic acid 2,2,2-trichloro-ethyl ester (455934-66-4)

Guidance literature:

With water; acetic acid; In tetrahydrofuran; at 80 ℃; for 12h;

DOI:10.1016/S0957-4166(02)00180-5

Reference yield:

2,2,2-trichloroethyl (4R,5S,9R)-4-benzyloxy-9-tert-butyldimethylsiloxy-5-methyl-7-oxo-6-oxadec-(2E)-enoate (455934-76-6) → (7E,13E)-(4R,10S,15R,16S)-15-Benzyloxy-4,10,16-trimethyl-1,5,11-trioxa-cyclohexadeca-7,13-diene-2,6,12-trione (455934-70-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 93 percent / AcOH; H₂O / tetrahydrofuran / 12 h / 80 °C

2.1: 55 percent / DCC; DMAP / CH₂Cl₂ / 24 h / 20 °C

3.1: 86 percent / AcOH; H₂O / tetrahydrofuran / 12 h / 80 °C

4.1: 100 percent / AcOH; AcONa; Zn / tetrahydrofuran / 3 h / 20 °C

5.1: 2,4,6-trichlorobenzoyl chloride; Et₃N / tetrahydrofuran / 2 h / 20 °C

5.2: 0.067 g / DMAP / tetrahydrofuran; toluene / 3.5 h / 100 °C

With dmap; 2,4,6-trichlorobenzoyl chloride; water; sodium acetate; acetic acid; triethylamine; dicyclohexyl-carbodiimide; zinc; In tetrahydrofuran; dichloromethane; 5.1: Yamaguchi macrolactonization / 5.2: Yamaguchi macrolactonization;

DOI:10.1016/S0957-4166(02)00180-5

upstream raw materials:

3-(R)-t-butyldimethylsilyloxybutanoic acid

2,2,2-trichloroethyl (4R,5S)-4-benzyloxy-5-hydroxy-2(E)-hexenoate

Downstream raw materials:

(E)-(4R,5S)-4-Benzyloxy-5-((R)-3-hydroxy-butyryloxy)-hex-2-enoic acid 2,2,2-trichloro-ethyl ester

(7E,13E)-(4R,10S,15R,16S)-15-Benzyloxy-4,10,16-trimethyl-1,5,11-trioxa-cyclohexadeca-7,13-diene-2,6,12-trione

(E)-(4R,5S)-4-Benzyloxy-5-[(R)-3-((E)-(S)-5-hydroxy-hex-2-enoyloxy)-butyryloxy]-hex-2-enoic acid

(E)-(4R,5S)-4-Benzyloxy-5-[(R)-3-((E)-(S)-5-hydroxy-hex-2-enoyloxy)-butyryloxy]-hex-2-enoic acid 2,2,2-trichloro-ethyl ester