(1S,3R)-1-[(2R,3S,6R)-6-(Benzyloxymethyl)-5-methylene-3-(triethylsilyloxy)tetrahydropyran-2-yl]-5-(p-methoxybenzyloxy)-3-methyl-2-methylenepentan-1-ol

Base Information

Chemical Name:(1S,3R)-1-[(2R,3S,6R)-6-(Benzyloxymethyl)-5-methylene-3-(triethylsilyloxy)tetrahydropyran-2-yl]-5-(p-methoxybenzyloxy)-3-methyl-2-methylenepentan-1-ol
CAS No.:1416356-31-4
Molecular Formula:C₃₅H₅₂O₆Si
Molecular Weight:596.88
Hs Code.:

(1S,3R)-1-[(2R,3S,6R)-6-(Benzyloxymethyl)-5-methylene-3-(triethylsilyloxy)tetrahydropyran-2-yl]-5-(p-methoxybenzyloxy)-3-methyl-2-methylenepentan-1-ol

Synonyms:(1S,3R)-1-[(2R,3S,6R)-6-(Benzyloxymethyl)-5-methylene-3-(triethylsilyloxy)tetrahydropyran-2-yl]-5-(p-methoxybenzyloxy)-3-methyl-2-methylenepentan-1-ol

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Chemical Property of (1S,3R)-1-[(2R,3S,6R)-6-(Benzyloxymethyl)-5-methylene-3-(triethylsilyloxy)tetrahydropyran-2-yl]-5-(p-methoxybenzyloxy)-3-methyl-2-methylenepentan-1-ol

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Technology Process of (1S,3R)-1-[(2R,3S,6R)-6-(Benzyloxymethyl)-5-methylene-3-(triethylsilyloxy)tetrahydropyran-2-yl]-5-(p-methoxybenzyloxy)-3-methyl-2-methylenepentan-1-ol

There total 17 articles about (1S,3R)-1-[(2R,3S,6R)-6-(Benzyloxymethyl)-5-methylene-3-(triethylsilyloxy)tetrahydropyran-2-yl]-5-(p-methoxybenzyloxy)-3-methyl-2-methylenepentan-1-ol 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: 46.0%

: (3R)-1-[(2R,3S,6R)-6-(benzyloxymethyl)-5-methylene-3-(triethylsilyloxy)tetrahydropyran-2-yl]-5-(p-methoxybenzyloxy)-3-methyl-2-methylenepentan-1-one

: 1416356-16-5
(1R,3R)-1-[(2R,3S,6R)-6-(Benzyloxymethyl)-5-methylene-3-(triethylsilyloxy)tetrahydropyran-2-yl]-5-(p-methoxybenzyloxy)-3-methyl-2-methylenepentan-1-ol

: 1416356-31-4
(1S,3R)-1-[(2R,3S,6R)-6-(Benzyloxymethyl)-5-methylene-3-(triethylsilyloxy)tetrahydropyran-2-yl]-5-(p-methoxybenzyloxy)-3-methyl-2-methylenepentan-1-ol

Guidance literature:: With zinc(II) tetrahydroborate; In diethyl ether; at -40 ℃; for 7.5h;
DOI:10.1246/bcsj.20120152

Reference yield:

: 1416356-29-0
C₂₇H₄₈O₄Si₂

: 1416356-16-5
(1R,3R)-1-[(2R,3S,6R)-6-(Benzyloxymethyl)-5-methylene-3-(triethylsilyloxy)tetrahydropyran-2-yl]-5-(p-methoxybenzyloxy)-3-methyl-2-methylenepentan-1-ol

: 1416356-31-4
(1S,3R)-1-[(2R,3S,6R)-6-(Benzyloxymethyl)-5-methylene-3-(triethylsilyloxy)tetrahydropyran-2-yl]-5-(p-methoxybenzyloxy)-3-methyl-2-methylenepentan-1-ol

Guidance literature:: Multi-step reaction with 6 steps

1: pyridinium p-toluenesulfonate / dichloromethane; methanol / 0.17 h / -10 °C

2: triethylamine; sulfur trioxide pyridine complex; dimethyl sulfoxide / dichloromethane / 0.5 h / 0 °C

3: sodium chlorite; 2-methyl-but-2-ene; sodium dihydrogenphosphate / water; tert-butyl alcohol / 2 h / 0 - 20 °C

4: dicyclohexyl-carbodiimide; dmap / dichloromethane / 16 h / 0 - 20 °C

5: tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; ((diphenylphosphoryl)oxy)copper(I); triphenyl-arsane / tetrahydrofuran / 3 h / 20 °C

6: zinc(II) tetrahydroborate / diethyl ether / 7.5 h / -40 °C

With dmap; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium chlorite; sodium dihydrogenphosphate; zinc(II) tetrahydroborate; 2-methyl-but-2-ene; ((diphenylphosphoryl)oxy)copper(I); triphenyl-arsane; sulfur trioxide pyridine complex; pyridinium p-toluenesulfonate; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; tert-butyl alcohol; 2: |Parikh-Doering Oxidation;
DOI:10.1246/bcsj.20120152

Reference yield:

: 1268455-54-4
C₁₅H₁₈O₄

: 1416356-16-5
(1R,3R)-1-[(2R,3S,6R)-6-(Benzyloxymethyl)-5-methylene-3-(triethylsilyloxy)tetrahydropyran-2-yl]-5-(p-methoxybenzyloxy)-3-methyl-2-methylenepentan-1-ol

: 1416356-31-4
(1S,3R)-1-[(2R,3S,6R)-6-(Benzyloxymethyl)-5-methylene-3-(triethylsilyloxy)tetrahydropyran-2-yl]-5-(p-methoxybenzyloxy)-3-methyl-2-methylenepentan-1-ol

Guidance literature:: Multi-step reaction with 10 steps

1: sodium hydride / N,N-dimethyl-formamide / 0 - 20 °C

2: camphor-10-sulfonic acid / dichloromethane; methanol / 20 °C

3: 1H-imidazole / N,N-dimethyl-formamide / 61.5 h / 50 °C

4: pyridinium p-toluenesulfonate / dichloromethane; methanol / 0.17 h / -10 °C

5: triethylamine; sulfur trioxide pyridine complex; dimethyl sulfoxide / dichloromethane / 0.5 h / 0 °C

6: sodium chlorite; 2-methyl-but-2-ene; sodium dihydrogenphosphate / water; tert-butyl alcohol / 2 h / 0 - 20 °C

7: dicyclohexyl-carbodiimide; dmap / dichloromethane / 16 h / 0 - 20 °C

8: 1H-imidazole / N,N-dimethyl-formamide / 46 h / 50 °C

9: tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; ((diphenylphosphoryl)oxy)copper(I); triphenyl-arsane / tetrahydrofuran / 3 h / 20 °C

10: zinc(II) tetrahydroborate / diethyl ether / 7.5 h / -40 °C

With 1H-imidazole; dmap; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium chlorite; sodium dihydrogenphosphate; zinc(II) tetrahydroborate; 2-methyl-but-2-ene; ((diphenylphosphoryl)oxy)copper(I); triphenyl-arsane; camphor-10-sulfonic acid; sulfur trioxide pyridine complex; pyridinium p-toluenesulfonate; sodium hydride; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 5: |Parikh-Doering Oxidation;
DOI:10.1246/bcsj.20120152