(4S,5S)-4-{(R)-[(4R,5S)-5-((5R,6R)-5-Benzyloxy-1-hydroxy-6-methyl-7-phenyl-hept-2-ynyl)-2,2-diethyl-[1,3]dioxolan-4-yl]-ethoxycarbonyl-trimethylsilanyloxy-methyl}-2,2-dimethyl-[1,3]dioxolane-4,5-dicarboxylic acid dimethyl ester

Base Information

Chemical Name:(4S,5S)-4-{(R)-[(4R,5S)-5-((5R,6R)-5-Benzyloxy-1-hydroxy-6-methyl-7-phenyl-hept-2-ynyl)-2,2-diethyl-[1,3]dioxolan-4-yl]-ethoxycarbonyl-trimethylsilanyloxy-methyl}-2,2-dimethyl-[1,3]dioxolane-4,5-dicarboxylic acid dimethyl ester
CAS No.:871514-76-0
Molecular Formula:C₄₄H₆₂O₁₃Si
Molecular Weight:827.054
Hs Code.:

(4S,5S)-4-{(R)-[(4R,5S)-5-((5R,6R)-5-Benzyloxy-1-hydroxy-6-methyl-7-phenyl-hept-2-ynyl)-2,2-diethyl-[1,3]dioxolan-4-yl]-ethoxycarbonyl-trimethylsilanyloxy-methyl}-2,2-dimethyl-[1,3]dioxolane-4,5-dicarboxylic acid dimethyl ester

Synonyms:(4S,5S)-4-{(R)-[(4R,5S)-5-((5R,6R)-5-Benzyloxy-1-hydroxy-6-methyl-7-phenyl-hept-2-ynyl)-2,2-diethyl-[1,3]dioxolan-4-yl]-ethoxycarbonyl-trimethylsilanyloxy-methyl}-2,2-dimethyl-[1,3]dioxolane-4,5-dicarboxylic acid dimethyl ester

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Chemical Property of (4S,5S)-4-{(R)-[(4R,5S)-5-((5R,6R)-5-Benzyloxy-1-hydroxy-6-methyl-7-phenyl-hept-2-ynyl)-2,2-diethyl-[1,3]dioxolan-4-yl]-ethoxycarbonyl-trimethylsilanyloxy-methyl}-2,2-dimethyl-[1,3]dioxolane-4,5-dicarboxylic acid dimethyl ester

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Technology Process of (4S,5S)-4-{(R)-[(4R,5S)-5-((5R,6R)-5-Benzyloxy-1-hydroxy-6-methyl-7-phenyl-hept-2-ynyl)-2,2-diethyl-[1,3]dioxolan-4-yl]-ethoxycarbonyl-trimethylsilanyloxy-methyl}-2,2-dimethyl-[1,3]dioxolane-4,5-dicarboxylic acid dimethyl ester

There total 24 articles about (4S,5S)-4-{(R)-[(4R,5S)-5-((5R,6R)-5-Benzyloxy-1-hydroxy-6-methyl-7-phenyl-hept-2-ynyl)-2,2-diethyl-[1,3]dioxolan-4-yl]-ethoxycarbonyl-trimethylsilanyloxy-methyl}-2,2-dimethyl-[1,3]dioxolane-4,5-dicarboxylic acid dimethyl ester 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: 97.0%

: 191935-31-6
(4R,5R)-4-benzyloxy-5-methyl-6-phenyl-1-hexyne

: 191935-30-5
3-ethyl 1,2-dimethyl (1S,2S,3R,4R,5R)-4,5-(diethylmethylenedioxy)-1,2-(dimethylmethylenedioxy)-5-formyl-3-(trimethylsilyloxy)pentane-1,2,3-tricarboxylate

: 871514-76-0
(4S,5S)-4-{(R)-[(4R,5S)-5-((5R,6R)-5-Benzyloxy-1-hydroxy-6-methyl-7-phenyl-hept-2-ynyl)-2,2-diethyl-[1,3]dioxolan-4-yl]-ethoxycarbonyl-trimethylsilanyloxy-methyl}-2,2-dimethyl-[1,3]dioxolane-4,5-dicarboxylic acid dimethyl ester

Guidance literature:: (4R,5R)-4-benzyloxy-5-methyl-6-phenyl-1-hexyne; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.75h;

3-ethyl 1,2-dimethyl (1S,2S,3R,4R,5R)-4,5-(diethylmethylenedioxy)-1,2-(dimethylmethylenedioxy)-5-formyl-3-(trimethylsilyloxy)pentane-1,2,3-tricarboxylate; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;
DOI:10.1016/j.tet.2005.09.030

Reference yield:

: 871514-68-0
(4R,5S)-2,2-Diethyl-5-(2-methoxy-ethoxymethoxymethyl)-[1,3]dioxolane-4-carbaldehyde

: 871514-76-0
(4S,5S)-4-{(R)-[(4R,5S)-5-((5R,6R)-5-Benzyloxy-1-hydroxy-6-methyl-7-phenyl-hept-2-ynyl)-2,2-diethyl-[1,3]dioxolan-4-yl]-ethoxycarbonyl-trimethylsilanyloxy-methyl}-2,2-dimethyl-[1,3]dioxolane-4,5-dicarboxylic acid dimethyl ester

Guidance literature:: Multi-step reaction with 16 steps

1.1: 79 percent / NaH₂PO₄; 2-methyl-2-butene; NaClO₂ / H₂O; 2-methyl-propan-2-ol / 8 h / 20 °C

2.1: 89 percent / diethyl cyanophosphonate; Et₃N / dimethylformamide / 1.5 h / 20 °C

3.1: tert-butyllithium / pentane; tetrahydrofuran / 0.5 h / -78 - 0 °C

3.2: 90 percent / tetrahydrofuran; pentane / 0.5 h / -78 °C

4.1: ozone / CH₂Cl₂ / 0.17 h / -78 °C

4.2: 86 percent / Me₂S / CH₂Cl₂ / 1 h / -78 - 20 °C

5.1: KHMDS / tetrahydrofuran; toluene / 0.5 h / -78 °C

5.2: 12 percent / tetrahydrofuran; toluene / -78 - -23 °C

6.1: 23 percent / KHMDS / toluene; tetrahydrofuran / -78 - -23 °C

7.1: 87 percent / Hg(OCOCF₃)2 / methanol / 10 h / Heating

8.1: 2.47 g / hydrogen / palladium hydroxide on carbon / ethyl acetate / 10 h / 760 Torr

9.1: 2.14 g / Dess-Martin periodinane / CH₂Cl₂ / 8 h / 20 °C

10.1: 2.31 g / NaH₂PO₄; 2-methyl-2-butene; NaClO₂ / H₂O; 2-methyl-propan-2-ol / 2.5 h / 20 °C

11.1: 1.81 g / diethyl ether / 0.17 h / 0 °C

12.1: 94 percent / sodium iodide; chlorotrimethylsilane / acetonitrile / 2 h / -23 °C

13.1: 1.42 g / 3 h / 90 °C

14.1: 87 percent / HCl / diethyl ether; H₂O / 1.5 h / 20 °C

15.1: 91 percent / Dess-Martin periodinane / CH₂Cl₂ / 3.5 h / 20 °C

16.1: butyllithium / hexane; tetrahydrofuran / 0.75 h / -78 °C

16.2: 97 percent / tetrahydrofuran; hexane / 0.5 h / -78 °C

With hydrogenchloride; sodium chlorite; sodium dihydrogenphosphate; n-butyllithium; chloro-trimethyl-silane; 2-methyl-but-2-ene; diethyl cyanophosphonate; hydrogen; tert.-butyl lithium; mercury(II) trifluoroacetate; potassium hexamethylsilazane; Dess-Martin periodane; ozone; triethylamine; sodium iodide; palladium dihydroxide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol; pentane; 6.1: aldol coupling;
DOI:10.1016/j.tet.2005.09.030

Reference yield:

: (4S,5R)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolane-4-carbonyl chloride

: 871514-76-0
(4S,5S)-4-{(R)-[(4R,5S)-5-((5R,6R)-5-Benzyloxy-1-hydroxy-6-methyl-7-phenyl-hept-2-ynyl)-2,2-diethyl-[1,3]dioxolan-4-yl]-ethoxycarbonyl-trimethylsilanyloxy-methyl}-2,2-dimethyl-[1,3]dioxolane-4,5-dicarboxylic acid dimethyl ester

Guidance literature:: Multi-step reaction with 14 steps

1.1: 77 percent / n-Bu₄NI / CH₂Cl₂; H₂O / 0.17 h / 0 °C

2.1: butyllithium; 1,1,1,3,3,3-hexamethyldisilazane / hexane; tetrahydrofuran / 0.5 h / -78 °C

2.2: 95 percent / tetrahydrofuran; hexane / -78 - 20 °C

3.1: 32 percent / Sn(OTf)2 / various solvent(s) / 1.5 h / -70 °C

4.1: 23 percent / KHMDS / toluene; tetrahydrofuran / -78 - -23 °C

5.1: 87 percent / Hg(OCOCF₃)2 / methanol / 10 h / Heating

6.1: 2.47 g / hydrogen / palladium hydroxide on carbon / ethyl acetate / 10 h / 760 Torr

7.1: 2.14 g / Dess-Martin periodinane / CH₂Cl₂ / 8 h / 20 °C

8.1: 2.31 g / NaH₂PO₄; 2-methyl-2-butene; NaClO₂ / H₂O; 2-methyl-propan-2-ol / 2.5 h / 20 °C

9.1: 1.81 g / diethyl ether / 0.17 h / 0 °C

10.1: 94 percent / sodium iodide; chlorotrimethylsilane / acetonitrile / 2 h / -23 °C

11.1: 1.42 g / 3 h / 90 °C

12.1: 87 percent / HCl / diethyl ether; H₂O / 1.5 h / 20 °C

13.1: 91 percent / Dess-Martin periodinane / CH₂Cl₂ / 3.5 h / 20 °C

14.1: butyllithium / hexane; tetrahydrofuran / 0.75 h / -78 °C

14.2: 97 percent / tetrahydrofuran; hexane / 0.5 h / -78 °C

With hydrogenchloride; sodium chlorite; sodium dihydrogenphosphate; tin(II) trifluoromethanesulfonate; n-butyllithium; chloro-trimethyl-silane; 2-methyl-but-2-ene; hydrogen; mercury(II) trifluoroacetate; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; Dess-Martin periodane; 1,1,1,3,3,3-hexamethyl-disilazane; sodium iodide; palladium dihydroxide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; ethyl acetate; toluene; acetonitrile; tert-butyl alcohol; 4.1: aldol coupling;
DOI:10.1016/j.tet.2005.09.030