(2S,3S,6R)-2-{(1R,3R,9S)-10-benzyloxy-1,9-bis(t-butyldimethylsilyloxy)-3-methyl-2,6-dimethylene-5-oxodecyl}-6-(benzyloxymethyl)-5-methylenetetrahydropyran-3-yl acetate

Base Information

• Chemical Name: (2S,3S,6R)-2-{(1R,3R,9S)-10-benzyloxy-1,9-bis(t-butyldimethylsilyloxy)-3-methyl-2,6-dimethylene-5-oxodecyl}-6-(benzyloxymethyl)-5-methylenetetrahydropyran-3-yl acetate
• CAS No.: 1416356-01-8
• Molecular Formula: C₄₈H₇₄O₈Si₂
• Molecular Weight: 835.282

Synonyms:(2S,3S,6R)-2-{(1R,3R,9S)-10-benzyloxy-1,9-bis(t-butyldimethylsilyloxy)-3-methyl-2,6-dimethylene-5-oxodecyl}-6-(benzyloxymethyl)-5-methylenetetrahydropyran-3-yl acetate

Chemical Property of (2S,3S,6R)-2-{(1R,3R,9S)-10-benzyloxy-1,9-bis(t-butyldimethylsilyloxy)-3-methyl-2,6-dimethylene-5-oxodecyl}-6-(benzyloxymethyl)-5-methylenetetrahydropyran-3-yl acetate

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of (2S,3S,6R)-2-{(1R,3R,9S)-10-benzyloxy-1,9-bis(t-butyldimethylsilyloxy)-3-methyl-2,6-dimethylene-5-oxodecyl}-6-(benzyloxymethyl)-5-methylenetetrahydropyran-3-yl acetate

There total 32 articles about (2S,3S,6R)-2-{(1R,3R,9S)-10-benzyloxy-1,9-bis(t-butyldimethylsilyloxy)-3-methyl-2,6-dimethylene-5-oxodecyl}-6-(benzyloxymethyl)-5-methylenetetrahydropyran-3-yl acetate 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: 87.0%

(2S,3S,6R)-6-benzyloxymethyl-2-{(1R,3R)-1-(t-butyldimethylsilyloxy)-3-methyl-2-methylene-5-oxo-5-(p-tolylthio)pentyl}-5-methylenetetrahydropyran-3-yl acetate (1416356-04-1) + C31H58O2SiSn (1268455-37-3) → (2S,3S,6R)-2-{(1R,3R,9S)-10-benzyloxy-1,9-bis(t-butyldimethylsilyloxy)-3-methyl-2,6-dimethylene-5-oxodecyl}-6-(benzyloxymethyl)-5-methylenetetrahydropyran-3-yl acetate (1416356-01-8)

Guidance literature:

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; ((diphenylphosphoryl)oxy)copper(I); triphenyl-arsane; In tetrahydrofuran; at 20 ℃; for 4h;

DOI:10.1246/bcsj.20120152

Reference yield:

C21H32O5Si → (2S,3S,6R)-2-{(1R,3R,9S)-10-benzyloxy-1,9-bis(t-butyldimethylsilyloxy)-3-methyl-2,6-dimethylene-5-oxodecyl}-6-(benzyloxymethyl)-5-methylenetetrahydropyran-3-yl acetate (1416356-01-8)

Guidance literature:

Multi-step reaction with 11 steps

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

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

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

4: 2,6-dimethylpyridine / dichloromethane / 1 h / 0 - 20 °C

5: pyridinium p-toluenesulfonate / dichloromethane; methanol / 9 h / 0 - 20 °C

6: pyridine; dmap / tetrahydrofuran / 15.5 h / 0 - 20 °C

7: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1 h / 0 - 20 °C / pH 7

8: Dess-Martin periodane / dichloromethane / 3 h / 0 - 20 °C

9: sodium chlorite; 2-methyl-but-2-ene; sodium dihydrogenphosphate / water; tert-butyl alcohol / 1 h / 0 - 20 °C

10: dicyclohexyl-carbodiimide; dmap / dichloromethane / 15 h / 0 - 20 °C

11: tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; ((diphenylphosphoryl)oxy)copper(I); triphenyl-arsane / tetrahydrofuran / 4 h / 20 °C

With pyridine; 2,6-dimethylpyridine; 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; pyridinium p-toluenesulfonate; Dess-Martin periodane; dicyclohexyl-carbodiimide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; tert-butyl alcohol;

DOI:10.1246/bcsj.20120152

Reference yield:

C15H18O4 (1268455-54-4) → (2S,3S,6R)-2-{(1R,3R,9S)-10-benzyloxy-1,9-bis(t-butyldimethylsilyloxy)-3-methyl-2,6-dimethylene-5-oxodecyl}-6-(benzyloxymethyl)-5-methylenetetrahydropyran-3-yl acetate (1416356-01-8)

Guidance literature:

Multi-step reaction with 17 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: tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; ((diphenylphosphoryl)oxy)copper(I); triphenyl-arsane / tetrahydrofuran / 3 h / 20 °C

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

10: 2,6-dimethylpyridine / dichloromethane / 1 h / 0 - 20 °C

11: pyridinium p-toluenesulfonate / dichloromethane; methanol / 9 h / 0 - 20 °C

12: pyridine; dmap / tetrahydrofuran / 15.5 h / 0 - 20 °C

13: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1 h / 0 - 20 °C / pH 7

14: Dess-Martin periodane / dichloromethane / 3 h / 0 - 20 °C

15: sodium chlorite; 2-methyl-but-2-ene; sodium dihydrogenphosphate / water; tert-butyl alcohol / 1 h / 0 - 20 °C

16: dicyclohexyl-carbodiimide; dmap / dichloromethane / 15 h / 0 - 20 °C

17: tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; ((diphenylphosphoryl)oxy)copper(I); triphenyl-arsane / tetrahydrofuran / 4 h / 20 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; 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; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 5: |Parikh-Doering Oxidation;

DOI:10.1246/bcsj.20120152

upstream raw materials:

S-(p-tolyl)(2S,3S,6R)-6-(benzyloxymethyl)-5-methylene-3-(triethylsilyloxy)tetrahydropyran-2-carboxylate

S-(p-tolyl)(2S,3S,6R)-6-(benzyloxymethyl)-3-hydroxy-5-methylenetetrahydropyran-2-carboxylate

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

(2S,3S,6R)-6-benzyloxymethyl-2-[(1R,3R)-1-(t-butyldimethylsilyloxy)-3-methyl-2-methylene-5-(p-methoxybenzyloxy)pentyl]-5-methylenetetrahydropyran-3-yl acetate

Downstream raw materials:

(2R,3S,6R)-{(1R,3R,9S)-10-benzyloxy-1,9-dihydroxy-3-methyl-2,6-dimethylene-5-oxodecyl}-6-benzyloxymethyl-5-methylenetetrahydropyran-3-yl acetate

(1R,3R,9S)-10-benzyloxy-1-{(2S,3S,6R)-6-benzyloxymethyl-3-hydroxy-5-methylenetetrahydropyran-2-yl}-9-hydroxy-3-methyl-2,6-dimethylene-5-oxodecyl acetate

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