1-[(6-{(1R)-2-hydroxy-1-[(4-methoxyphenyl)methoxy]ethyl}(4S,6R)-2,2-dimethyl(1,3-dioxan-4-yl))methyl](1R,2R)-2-[(phenylmethoxy)methoxy]propyl 2,2-dimethylpropanoate

Base Information

• Chemical Name: 1-[(6-{(1R)-2-hydroxy-1-[(4-methoxyphenyl)methoxy]ethyl}(4S,6R)-2,2-dimethyl(1,3-dioxan-4-yl))methyl](1R,2R)-2-[(phenylmethoxy)methoxy]propyl 2,2-dimethylpropanoate
• CAS No.: 850534-32-6
• Molecular Formula: C₃₃H₄₈O₉
• Molecular Weight: 588.739
• Mol file: 850534-32-6.mol

Synonyms:1-[(6-{(1R)-2-hydroxy-1-[(4-methoxyphenyl)methoxy]ethyl}(4S,6R)-2,2-dimethyl(1,3-dioxan-4-yl))methyl](1R,2R)-2-[(phenylmethoxy)methoxy]propyl 2,2-dimethylpropanoate

Chemical Property of 1-[(6-{(1R)-2-hydroxy-1-[(4-methoxyphenyl)methoxy]ethyl}(4S,6R)-2,2-dimethyl(1,3-dioxan-4-yl))methyl](1R,2R)-2-[(phenylmethoxy)methoxy]propyl 2,2-dimethylpropanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[(6-{(1R)-2-hydroxy-1-[(4-methoxyphenyl)methoxy]ethyl}(4S,6R)-2,2-dimethyl(1,3-dioxan-4-yl))methyl](1R,2R)-2-[(phenylmethoxy)methoxy]propyl 2,2-dimethylpropanoate

There total 12 articles about 1-[(6-{(1R)-2-hydroxy-1-[(4-methoxyphenyl)methoxy]ethyl}(4S,6R)-2,2-dimethyl(1,3-dioxan-4-yl))methyl](1R,2R)-2-[(phenylmethoxy)methoxy]propyl 2,2-dimethylpropanoate 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: 98.0%

1-[(6-{(1R)-1-[(4-methoxyphenyl)methoxy]-2-(1,1,2,2-tetramethyl-1-silapropoxy)ethyl}(4S,6R)-2,2-dimethyl(1,3-dioxan-4-yl))methyl](1R,2R)-2-[(phenylmethoxy)methoxy]propyl 2,2-dimethylpropanoate (850534-31-5) → 1-[(6-{(1R)-2-hydroxy-1-[(4-methoxyphenyl)methoxy]ethyl}(4S,6R)-2,2-dimethyl(1,3-dioxan-4-yl))methyl](1R,2R)-2-[(phenylmethoxy)methoxy]propyl 2,2-dimethylpropanoate (850534-32-6)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 0.5h;

DOI:10.1021/jo048308m

Reference yield:

(2R,3R)-5-(chloromethyl)-2-[(phenylmethoxy)methoxy]hex-5-en-3-ol (850534-25-7) → 1-[(6-{(1R)-2-hydroxy-1-[(4-methoxyphenyl)methoxy]ethyl}(4S,6R)-2,2-dimethyl(1,3-dioxan-4-yl))methyl](1R,2R)-2-[(phenylmethoxy)methoxy]propyl 2,2-dimethylpropanoate (850534-32-6)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 81 percent / pyridine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 24 h / 20 °C

2.1: (i-Pr)2NH; n-BuLi; Bu₃SnH / tetrahydrofuran; hexane / 0.5 h / -78 °C

2.2: BF₃*OEt₂

3.1: O₃ / CH₂Cl₂ / -90 °C

3.2: 86 percent / Ph₃P / CH₂Cl₂ / -90 - 20 °C

4.1: 92 percent / Et₂BOMe; NaBH₄ / tetrahydrofuran / 9 h / -78 °C

5.1: 100 percent / TsOH*H₂O / 1 h / 20 °C

6.1: 98 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C

With pyridine; dmap; sodium tetrahydroborate; n-butyllithium; diethyl methoxy borane; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; toluene-4-sulfonic acid; ozone; diisopropylamine; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1021/jo048308m

Reference yield:

3-(tert-butyldimethylsilanyloxy)-2-(4-methoxybenzyloxy)propionaldehyde → 1-[(6-{(1R)-2-hydroxy-1-[(4-methoxyphenyl)methoxy]ethyl}(4S,6R)-2,2-dimethyl(1,3-dioxan-4-yl))methyl](1R,2R)-2-[(phenylmethoxy)methoxy]propyl 2,2-dimethylpropanoate (850534-32-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: (i-Pr)2NH; n-BuLi; Bu₃SnH / tetrahydrofuran; hexane / 0.5 h / -78 °C

1.2: BF₃*OEt₂

2.1: O₃ / CH₂Cl₂ / -90 °C

2.2: 86 percent / Ph₃P / CH₂Cl₂ / -90 - 20 °C

3.1: 92 percent / Et₂BOMe; NaBH₄ / tetrahydrofuran / 9 h / -78 °C

4.1: 100 percent / TsOH*H₂O / 1 h / 20 °C

5.1: 98 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C

With sodium tetrahydroborate; n-butyllithium; diethyl methoxy borane; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; toluene-4-sulfonic acid; ozone; diisopropylamine; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1021/jo048308m

upstream raw materials:

1-[(6-{(1R)-1-[(4-methoxyphenyl)methoxy]-2-(1,1,2,2-tetramethyl-1-silapropoxy)ethyl}(4S,6R)-2,2-dimethyl(1,3-dioxan-4-yl))methyl](1R,2R)-2-[(phenylmethoxy)methoxy]propyl 2,2-dimethylpropanoate

(2R,3R)-5-(chloromethyl)-2-[(phenylmethoxy)methoxy]hex-5-en-3-ol

2,2-Dimethyl-propionic acid (R)-1-((R)-1-benzyloxymethoxy-ethyl)-3-chloromethyl-but-3-enyl ester

1,6-di-O-(tert-butyldimethylsilyl)-2,5-di-O-(p-methoxybenzyl)-D-mannitol

Downstream raw materials:

(1R,2R)-1-{[(6S)-6-(1,1-dimethylprop-2-enyl)-6-methoxy-5-oxo(3,4,5,6-tetrahydro-2H-pyran-2-yl)]methyl}-2-[(phenylmethoxy)methoxy]propyl 2,2-dimethylpropanoate

methyl 2-(6-{(2R,3R)-2-(2,2-dimethylpropanoyloxy)-3-[(phenylmethoxy)methoxy]butyl}(2S)-2-(1,1-dimethylprop-2-enyl)-2-methoxy-3-oxo-5,6-dihydro-2H-pyran-4-ylidene)acetate

(1R,2R)-1-{[(6S)-6-(1,1-dimethylprop-2-enyl)-6-methoxy-5-oxo(2,3,4,5-tetrahydropyran-2-yl)]methyl}-2-[(phenylmethoxy)methoxy]propyl 2,2-dimethylpropanoate

(1R,2R)-1-[(6-{(1S)-1-[(4-methoxyphenyl)methoxy]-3,3-dimethyl-2-oxopent-4-enyl}(4S,6R)-2,2-dimethyl(1,3-dioxan-4-yl))methyl]-2-[(phenylmethoxy)methoxy]propyl 2,2-dimethylpropanoate