(S)-benzyl 2-((2S,4R,6R)-tetrahydro-6-((2S,3S,4R)-2,4-bishydroxy-3-methyl-5-(6-methyl-2-methyloxycarbonyl-3,5-bistriisopropylsilyloxyphenyl)-pentyl)-5,5-dimethyl-4-tert-butyldimethylsilyloxy-2H-pyran-2-yl)-2-methoxyacetate

Base Information

• Chemical Name: (S)-benzyl 2-((2S,4R,6R)-tetrahydro-6-((2S,3S,4R)-2,4-bishydroxy-3-methyl-5-(6-methyl-2-methyloxycarbonyl-3,5-bistriisopropylsilyloxyphenyl)-pentyl)-5,5-dimethyl-4-tert-butyldimethylsilyloxy-2H-pyran-2-yl)-2-methoxyacetate
• CAS No.: 1213265-26-9
• Molecular Formula: C₅₆H₉₈O₁₁Si₃
• Molecular Weight: 1031.64

Synonyms:(S)-benzyl 2-((2S,4R,6R)-tetrahydro-6-((2S,3S,4R)-2,4-bishydroxy-3-methyl-5-(6-methyl-2-methyloxycarbonyl-3,5-bistriisopropylsilyloxyphenyl)-pentyl)-5,5-dimethyl-4-tert-butyldimethylsilyloxy-2H-pyran-2-yl)-2-methoxyacetate

Chemical Property of (S)-benzyl 2-((2S,4R,6R)-tetrahydro-6-((2S,3S,4R)-2,4-bishydroxy-3-methyl-5-(6-methyl-2-methyloxycarbonyl-3,5-bistriisopropylsilyloxyphenyl)-pentyl)-5,5-dimethyl-4-tert-butyldimethylsilyloxy-2H-pyran-2-yl)-2-methoxyacetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Useful:

Technology Process of (S)-benzyl 2-((2S,4R,6R)-tetrahydro-6-((2S,3S,4R)-2,4-bishydroxy-3-methyl-5-(6-methyl-2-methyloxycarbonyl-3,5-bistriisopropylsilyloxyphenyl)-pentyl)-5,5-dimethyl-4-tert-butyldimethylsilyloxy-2H-pyran-2-yl)-2-methoxyacetate

There total 22 articles about (S)-benzyl 2-((2S,4R,6R)-tetrahydro-6-((2S,3S,4R)-2,4-bishydroxy-3-methyl-5-(6-methyl-2-methyloxycarbonyl-3,5-bistriisopropylsilyloxyphenyl)-pentyl)-5,5-dimethyl-4-tert-butyldimethylsilyloxy-2H-pyran-2-yl)-2-methoxyacetate 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: 93.0%

(S)-benzyl 2-((2S,4R,6R)-tetrahydro-5,5-dimethyl-6-((3S,4R)-4-hydroxy-3-methyl-5-(6-methyl-2-methyloxycarbonyl-3,5-bistriisopropylsilyloxyphenyl)-2-oxopentyl)-4-tert-butyldimethylsilyloxy-2H-pyran-2-yl)-2-methoxyacetate (1213264-82-4) → (S)-benzyl 2-((2S,4R,6R)-tetrahydro-6-((2S,3S,4R)-2,4-bishydroxy-3-methyl-5-(6-methyl-2-methyloxycarbonyl-3,5-bistriisopropylsilyloxyphenyl)-pentyl)-5,5-dimethyl-4-tert-butyldimethylsilyloxy-2H-pyran-2-yl)-2-methoxyacetate (1213265-26-9)

Guidance literature:

With sodium tetrahydroborate; triethyl borane; In tetrahydrofuran; methanol; hexane; at -70 ℃; for 16h; optical yield given as %de; Inert atmosphere;

DOI:10.1021/ol1000389

Reference yield:

(3R)-7-((4-methoxybenzyl)oxy)-2,2-dimethyl-1-((tetrahydro-2H-pyran-2-yl)oxy)hept-5-yn-3-ol (1213264-68-6) → (S)-benzyl 2-((2S,4R,6R)-tetrahydro-6-((2S,3S,4R)-2,4-bishydroxy-3-methyl-5-(6-methyl-2-methyloxycarbonyl-3,5-bistriisopropylsilyloxyphenyl)-pentyl)-5,5-dimethyl-4-tert-butyldimethylsilyloxy-2H-pyran-2-yl)-2-methoxyacetate (1213265-26-9)

Guidance literature:

Multi-step reaction with 20 steps

1.1: pyridinium p-toluenesulfonate / ethanol / 19 h / 70 °C / Inert atmosphere

2.1: [bis(acetoxy)iodo]benzene; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / dichloromethane / 8 h / 20 °C / Inert atmosphere

3.1: magnesium bromide ethyl etherate / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

3.2: 12 h / 0 °C / Inert atmosphere

4.1: 1H-imidazole / N,N-dimethyl-formamide / 1.5 h / 0 °C / Inert atmosphere

5.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 13 h / -30 - 0 °C / pH 7 / Inert atmosphere

6.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene; tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere

7.1: diethyl (2S,3S)-tartrate; titanium(IV) isopropylate; tert.-butylhydroperoxide / dichloromethane / 2 h / -20 °C / Inert atmosphere; Molecular sieve

8.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 5.5 h / 0 °C / Inert atmosphere

9.1: camphor-10-sulfonic acid / methanol; dichloromethane / 19 h / 0 - 20 °C / Inert atmosphere

10.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

10.2: 2 h / 0 °C / Inert atmosphere

11.1: 2,6-dimethylpyridine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

12.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / tetrahydrofuran; water / 10.5 h / 0 - 20 °C / Inert atmosphere

13.1: sodium periodate / methanol; water / 0.5 h / 20 °C / Inert atmosphere

14.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

15.1: 1‐methyl‐2‐azaadamantane‐N‐oxyl; [bis(acetoxy)iodo]benzene / dichloromethane / 16 h / 20 °C / Inert atmosphere

16.1: hydrogen; palladium(II) hydroxide / methanol / 0.67 h / 20 °C / 760.05 Torr

17.1: sodium chlorite; 1-Me-AZADO⁽¹⁺⁾BF₄^(1-) / acetonitrile / 0.5 h / 20 °C / pH 7 / Inert atmosphere

18.1: caesium carbonate / N,N-dimethyl-formamide / 1 h / 0 °C / Inert atmosphere

19.1: phenylborondichloride / dichloromethane / 0.33 h / -78 °C / Inert atmosphere

19.2: 1 h / -78 °C / Inert atmosphere

19.3: 1 h / -78 °C / Inert atmosphere

20.1: triethyl borane / methanol; tetrahydrofuran; hexane / 0.5 h / -70 °C / Inert atmosphere

20.2: 16 h / -70 °C / Inert atmosphere

With 1H-imidazole; 1‐methyl‐2‐azaadamantane‐N‐oxyl; 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium chlorite; sodium periodate; osmium(VIII) oxide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; diethyl (2S,3S)-tartrate; triethyl borane; [bis(acetoxy)iodo]benzene; 1-Me-AZADO⁽¹⁺⁾BF₄^(1-); camphor-10-sulfonic acid; phenylborondichloride; hydrogen; palladium(II) hydroxide; pyridinium p-toluenesulfonate; sodium hydride; caesium carbonate; magnesium bromide ethyl etherate; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium diisopropyl amide; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; 7.1: |Sharpless Asymmetric Epoxidation;

DOI:10.1021/acs.joc.5b02256

Reference yield:

(R)-7-((4-methoxybenzyl)oxy)-2,2-dimethylhept-5-yne-1,3-diol (1213265-03-2) → (S)-benzyl 2-((2S,4R,6R)-tetrahydro-6-((2S,3S,4R)-2,4-bishydroxy-3-methyl-5-(6-methyl-2-methyloxycarbonyl-3,5-bistriisopropylsilyloxyphenyl)-pentyl)-5,5-dimethyl-4-tert-butyldimethylsilyloxy-2H-pyran-2-yl)-2-methoxyacetate (1213265-26-9)

Guidance literature:

Multi-step reaction with 19 steps

1.1: [bis(acetoxy)iodo]benzene; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / dichloromethane / 8 h / 20 °C / Inert atmosphere

2.1: magnesium bromide ethyl etherate / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

2.2: 12 h / 0 °C / Inert atmosphere

3.1: 1H-imidazole / N,N-dimethyl-formamide / 1.5 h / 0 °C / Inert atmosphere

4.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 13 h / -30 - 0 °C / pH 7 / Inert atmosphere

5.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene; tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere

6.1: diethyl (2S,3S)-tartrate; titanium(IV) isopropylate; tert.-butylhydroperoxide / dichloromethane / 2 h / -20 °C / Inert atmosphere; Molecular sieve

7.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 5.5 h / 0 °C / Inert atmosphere

8.1: camphor-10-sulfonic acid / methanol; dichloromethane / 19 h / 0 - 20 °C / Inert atmosphere

9.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

9.2: 2 h / 0 °C / Inert atmosphere

10.1: 2,6-dimethylpyridine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

11.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / tetrahydrofuran; water / 10.5 h / 0 - 20 °C / Inert atmosphere

12.1: sodium periodate / methanol; water / 0.5 h / 20 °C / Inert atmosphere

13.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

14.1: 1‐methyl‐2‐azaadamantane‐N‐oxyl; [bis(acetoxy)iodo]benzene / dichloromethane / 16 h / 20 °C / Inert atmosphere

15.1: hydrogen; palladium(II) hydroxide / methanol / 0.67 h / 20 °C / 760.05 Torr

16.1: sodium chlorite; 1-Me-AZADO⁽¹⁺⁾BF₄^(1-) / acetonitrile / 0.5 h / 20 °C / pH 7 / Inert atmosphere

17.1: caesium carbonate / N,N-dimethyl-formamide / 1 h / 0 °C / Inert atmosphere

18.1: phenylborondichloride / dichloromethane / 0.33 h / -78 °C / Inert atmosphere

18.2: 1 h / -78 °C / Inert atmosphere

18.3: 1 h / -78 °C / Inert atmosphere

19.1: triethyl borane / methanol; tetrahydrofuran; hexane / 0.5 h / -70 °C / Inert atmosphere

19.2: 16 h / -70 °C / Inert atmosphere

With 1H-imidazole; 1‐methyl‐2‐azaadamantane‐N‐oxyl; 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium chlorite; sodium periodate; osmium(VIII) oxide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; diethyl (2S,3S)-tartrate; triethyl borane; [bis(acetoxy)iodo]benzene; 1-Me-AZADO⁽¹⁺⁾BF₄^(1-); camphor-10-sulfonic acid; phenylborondichloride; hydrogen; palladium(II) hydroxide; sodium hydride; caesium carbonate; magnesium bromide ethyl etherate; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium diisopropyl amide; In tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; 6.1: |Sharpless Asymmetric Epoxidation;

DOI:10.1021/acs.joc.5b02256

upstream raw materials:

(S)-benzyl 2-((2S,4R,6R)-tetrahydro-5,5-dimethyl-6-((3S,4R)-4-hydroxy-3-methyl-5-(6-methyl-2-methyloxycarbonyl-3,5-bistriisopropylsilyloxyphenyl)-2-oxopentyl)-4-tert-butyldimethylsilyloxy-2H-pyran-2-yl)-2-methoxyacetate

(3R)-7-((4-methoxybenzyl)oxy)-2,2-dimethyl-1-((tetrahydro-2H-pyran-2-yl)oxy)hept-5-yn-3-ol

(R)-7-((4-methoxybenzyl)oxy)-2,2-dimethylhept-5-yne-1,3-diol

(R)-3-hydroxy-7-((4-methoxybenzyl)oxy)-2,2-dimethylhept-5-ynal

Downstream raw materials:

(S)-benzyl 2-((2S,4R,6R)-tetrahydro-6-((2S,3S)-3-((3R)-6,8-bistriisopropylsilyloxy-5-methyl-3,4-dihydroisocoumarinyl)-3-methyl-2-tert-butyldimethylsilyloxypropyl)-5,5-dimethyl-4-tert-butyldimethylsilyloxy-2H-pyran-2-yl)-2-methoxyacetate

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