(3S,6R,7S,8S)-3-Hydroxy-11-{2-[(E)-(S)-2-hydroxy-3-methyl-4-(2-methyl-thiazol-4-yl)-but-3-enyl]-phenyl}-4,4,6,8-tetramethyl-5-oxo-7-(2,2,2-trichloro-ethoxycarbonyloxy)-undecanoic acid tert-butyl ester

Base Information

• Chemical Name: (3S,6R,7S,8S)-3-Hydroxy-11-{2-[(E)-(S)-2-hydroxy-3-methyl-4-(2-methyl-thiazol-4-yl)-but-3-enyl]-phenyl}-4,4,6,8-tetramethyl-5-oxo-7-(2,2,2-trichloro-ethoxycarbonyloxy)-undecanoic acid tert-butyl ester
• CAS No.: 246530-11-0
• Molecular Formula: C₃₇H₅₂Cl₃NO₈S
• Molecular Weight: 777.247
• Mol file: 246530-11-0.mol

Synonyms:(3S,6R,7S,8S)-3-Hydroxy-11-{2-[(E)-(S)-2-hydroxy-3-methyl-4-(2-methyl-thiazol-4-yl)-but-3-enyl]-phenyl}-4,4,6,8-tetramethyl-5-oxo-7-(2,2,2-trichloro-ethoxycarbonyloxy)-undecanoic acid tert-butyl ester

Chemical Property of (3S,6R,7S,8S)-3-Hydroxy-11-{2-[(E)-(S)-2-hydroxy-3-methyl-4-(2-methyl-thiazol-4-yl)-but-3-enyl]-phenyl}-4,4,6,8-tetramethyl-5-oxo-7-(2,2,2-trichloro-ethoxycarbonyloxy)-undecanoic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,6R,7S,8S)-3-Hydroxy-11-{2-[(E)-(S)-2-hydroxy-3-methyl-4-(2-methyl-thiazol-4-yl)-but-3-enyl]-phenyl}-4,4,6,8-tetramethyl-5-oxo-7-(2,2,2-trichloro-ethoxycarbonyloxy)-undecanoic acid tert-butyl ester

There total 8 articles about (3S,6R,7S,8S)-3-Hydroxy-11-{2-[(E)-(S)-2-hydroxy-3-methyl-4-(2-methyl-thiazol-4-yl)-but-3-enyl]-phenyl}-4,4,6,8-tetramethyl-5-oxo-7-(2,2,2-trichloro-ethoxycarbonyloxy)-undecanoic acid tert-butyl 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%

(6R,7S,8S)-11-{2-[(E)-(S)-2-Hydroxy-3-methyl-4-(2-methyl-thiazol-4-yl)-but-3-enyl]-phenyl}-4,4,6,8-tetramethyl-3,5-dioxo-7-(2,2,2-trichloro-ethoxycarbonyloxy)-undecanoic acid tert-butyl ester (246529-72-6) → (3S,6R,7S,8S)-3-Hydroxy-11-{2-[(E)-(S)-2-hydroxy-3-methyl-4-(2-methyl-thiazol-4-yl)-but-3-enyl]-phenyl}-4,4,6,8-tetramethyl-5-oxo-7-(2,2,2-trichloro-ethoxycarbonyloxy)-undecanoic acid tert-butyl ester (246530-11-0)

Guidance literature:

With hydrogen; (R)-Ru-BINAP; under 62057.8 Torr;

DOI:10.1016/S0040-4039(99)01433-1

Reference yield:

(6R,7S,8S)-4,4,6,8-Tetramethyl-3,5-dioxo-7-(2,2,2-trichloro-ethoxycarbonyloxy)-undec-10-enoic acid tert-butyl ester (224580-52-3) → (3S,6R,7S,8S)-3-Hydroxy-11-{2-[(E)-(S)-2-hydroxy-3-methyl-4-(2-methyl-thiazol-4-yl)-but-3-enyl]-phenyl}-4,4,6,8-tetramethyl-5-oxo-7-(2,2,2-trichloro-ethoxycarbonyloxy)-undecanoic acid tert-butyl ester (246530-11-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: tetrahydrofuran

2.1: (R)-2-Me-CBS-oxazolidinone; BH₃*SMe₂

2.2: lutidine

2.3: Pd(dppf)Cl₂; Ph₃As; CsCO₃ / dimethylformamide

3.1: 72 percent / HF*pyridine

4.1: 82 percent / H₂ / (R)-Ru-BINAP / 62057.8 Torr

With dimethylsulfide borane complex; (R)-2-Me-CBS-oxazolidinone; hydrogen; pyridine hydrogenfluoride; (R)-Ru-BINAP; In tetrahydrofuran; 1.1: hydroboration / 2.1: Reduction / 2.2: O-silylation / 2.3: B-alkyl Suzuki coupling / 3.1: desilylation / 4.1: Hydrogenation;

DOI:10.1016/S0040-4039(99)01433-1

Reference yield:

2-Iodobenzyl bromide (40400-13-3) → (3S,6R,7S,8S)-3-Hydroxy-11-{2-[(E)-(S)-2-hydroxy-3-methyl-4-(2-methyl-thiazol-4-yl)-but-3-enyl]-phenyl}-4,4,6,8-tetramethyl-5-oxo-7-(2,2,2-trichloro-ethoxycarbonyloxy)-undecanoic acid tert-butyl ester (246530-11-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 67 percent / Zn; CuCN; LiCl

3.1: (R)-2-Me-CBS-oxazolidinone; BH₃*SMe₂

3.2: lutidine

3.3: Pd(dppf)Cl₂; Ph₃As; CsCO₃ / dimethylformamide

4.1: 72 percent / HF*pyridine

5.1: 82 percent / H₂ / (R)-Ru-BINAP / 62057.8 Torr

With dimethylsulfide borane complex; (R)-2-Me-CBS-oxazolidinone; hydrogen; pyridine hydrogenfluoride; lithium chloride; zinc; (R)-Ru-BINAP; 1.1: Condensation / 2.1: Oxidation / 3.1: Reduction / 3.2: O-silylation / 3.3: B-alkyl Suzuki coupling / 4.1: desilylation / 5.1: Hydrogenation;

DOI:10.1016/S0040-4039(99)01433-1

upstream raw materials:

(6R,7S,8S)-11-{2-[(E)-(S)-2-Hydroxy-3-methyl-4-(2-methyl-thiazol-4-yl)-but-3-enyl]-phenyl}-4,4,6,8-tetramethyl-3,5-dioxo-7-(2,2,2-trichloro-ethoxycarbonyloxy)-undecanoic acid tert-butyl ester

2-Iodobenzyl bromide

(E)-2-methyl-3-(2-methylthiazol-4-yl)acrylaldehyde

(E)-1-(2-Iodo-phenyl)-3-methyl-4-(2-methyl-thiazol-4-yl)-but-3-en-2-ol

Downstream raw materials:

(3S,6R,7S,8S)-11-{2-[(E)-(S)-2-Hydroxy-3-methyl-4-(2-methyl-thiazol-4-yl)-but-3-enyl]-phenyl}-4,4,6,8-tetramethyl-5-oxo-7-(2,2,2-trichloro-ethoxycarbonyloxy)-3-triethylsilanyloxy-undecanoic acid