(2R)-2-[(1R,3R)-3-{[tert-butyl(dimethyl)silyl]oxy}-6-[(4-methoxybenzyl)oxy]-1-(methoxymethoxy)hexyl]-4-pentenyl 4-methylbenzenesulfonate

Base Information

• Chemical Name: (2R)-2-[(1R,3R)-3-{[tert-butyl(dimethyl)silyl]oxy}-6-[(4-methoxybenzyl)oxy]-1-(methoxymethoxy)hexyl]-4-pentenyl 4-methylbenzenesulfonate
• CAS No.: 825612-64-4
• Molecular Formula: C₃₄H₅₄O₈SSi
• Molecular Weight: 650.949
• Mol file: 825612-64-4.mol

Synonyms:(2R)-2-[(1R,3R)-3-{[tert-butyl(dimethyl)silyl]oxy}-6-[(4-methoxybenzyl)oxy]-1-(methoxymethoxy)hexyl]-4-pentenyl 4-methylbenzenesulfonate

Chemical Property of (2R)-2-[(1R,3R)-3-{[tert-butyl(dimethyl)silyl]oxy}-6-[(4-methoxybenzyl)oxy]-1-(methoxymethoxy)hexyl]-4-pentenyl 4-methylbenzenesulfonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R)-2-[(1R,3R)-3-{[tert-butyl(dimethyl)silyl]oxy}-6-[(4-methoxybenzyl)oxy]-1-(methoxymethoxy)hexyl]-4-pentenyl 4-methylbenzenesulfonate

There total 7 articles about (2R)-2-[(1R,3R)-3-{[tert-butyl(dimethyl)silyl]oxy}-6-[(4-methoxybenzyl)oxy]-1-(methoxymethoxy)hexyl]-4-pentenyl 4-methylbenzenesulfonate 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%

(2R)-2-[(1R,3R)-3-{[tert-butyl(dimethyl)silyl]oxy}-6-[(4-methoxybenzyl)oxy]-1-(methoxymethoxy)hexyl]-4-penten-1-ol (825612-63-3) + p-toluenesulfonyl chloride (98-59-9) → (2R)-2-[(1R,3R)-3-{[tert-butyl(dimethyl)silyl]oxy}-6-[(4-methoxybenzyl)oxy]-1-(methoxymethoxy)hexyl]-4-pentenyl 4-methylbenzenesulfonate (825612-64-4)

Guidance literature:

With pyridine; at 23 ℃; for 12h;

DOI:10.1002/chem.200400617

Reference yield:

ethyl (3RS)-3-hydroxy-6-[(4-methoxybenzyl)oxy]hexanoate → (2R)-2-[(1R,3R)-3-{[tert-butyl(dimethyl)silyl]oxy}-6-[(4-methoxybenzyl)oxy]-1-(methoxymethoxy)hexyl]-4-pentenyl 4-methylbenzenesulfonate (825612-64-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 0 - 23 °C

2.1: 83 percent / DIBAL / CH₂Cl₂ / 2 h / -78 °C

3.1: (-)-sparteine / TiCl₄ / CH₂Cl₂ / 0.42 h / 0 °C

3.2: 68 percent / CH₂Cl₂ / 1 h / 0 °C

4.1: 82 percent / iPr₂NEt; Bu₄NI / CH₂Cl₂ / 72 h / 23 °C

5.1: 86 percent / aq. NaBH₄ / tetrahydrofuran / 12 h / 0 - 23 °C

6.1: 95 percent / pyridine / 12 h / 23 °C

With pyridine; 2,6-dimethylpyridine; sodium tetrahydroborate; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; (-)-sparteine; titanium tetrachloride; In tetrahydrofuran; dichloromethane;

DOI:10.1002/chem.200400617

Reference yield:

(3R)-3-{[tert-butyl(dimethyl)silyl]oxy}-6-[(4-methoxybenzyl)oxy]-hexanal (825612-52-0) → (2R)-2-[(1R,3R)-3-{[tert-butyl(dimethyl)silyl]oxy}-6-[(4-methoxybenzyl)oxy]-1-(methoxymethoxy)hexyl]-4-pentenyl 4-methylbenzenesulfonate (825612-64-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: (-)-sparteine / TiCl₄ / CH₂Cl₂ / 0.42 h / 0 °C

1.2: 68 percent / CH₂Cl₂ / 1 h / 0 °C

2.1: 82 percent / iPr₂NEt; Bu₄NI / CH₂Cl₂ / 72 h / 23 °C

3.1: 86 percent / aq. NaBH₄ / tetrahydrofuran / 12 h / 0 - 23 °C

4.1: 95 percent / pyridine / 12 h / 23 °C

With pyridine; sodium tetrahydroborate; tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine; (-)-sparteine; titanium tetrachloride; In tetrahydrofuran; dichloromethane;

DOI:10.1002/chem.200400617

upstream raw materials:

(2R)-2-[(1R,3R)-3-{[tert-butyl(dimethyl)silyl]oxy}-6-[(4-methoxybenzyl)oxy]-1-(methoxymethoxy)hexyl]-4-penten-1-ol

p-toluenesulfonyl chloride

(3R)-3-{[tert-butyl(dimethyl)silyl]oxy}-6-[(4-methoxybenzyl)oxy]-hexanal

ethyl (3R)-3-{[tert-butyl(dimethyl)silyl]oxy}-6-[(4-methoxybenzyl)oxy]-hexanoate

Downstream raw materials:

(3S,5R,6S)-14-methoxy-3-{3-[(4-methoxybenzyl)oxy]propyl}-5-(methoxymethoxy)-6-methyl-3,4,5,6,7,10-hexahydro-1H-2-benzoxacyclododecin-1-one

(-)-salicylihalamide A

(1S,3R,4S)-1-{3-[(4-methoxybenzyl)oxy]propyl}-3-(methoxymethoxy)-4-methyl-6-heptenyl 2-allyl-6-methoxybenzoate

salicylihalamide B