methanesulfonic acid 3-allyl-4-((R)-1-(S)-[(4S,6S)-4-(tert-butyl-dimethylsilanyloxymethyl)-2,2,6-trimethyl-[1,3]dioxan-4-yl]-hydroxy-methyl-allyl)-2-ethoxyphenyl ester

Base Information

Chemical Name:methanesulfonic acid 3-allyl-4-((R)-1-(S)-[(4S,6S)-4-(tert-butyl-dimethylsilanyloxymethyl)-2,2,6-trimethyl-[1,3]dioxan-4-yl]-hydroxy-methyl-allyl)-2-ethoxyphenyl ester
CAS No.:805239-95-6
Molecular Formula:C₃₀H₅₀O₈SSi
Molecular Weight:598.874
Hs Code.:

methanesulfonic acid 3-allyl-4-((R)-1-(S)-[(4S,6S)-4-(tert-butyl-dimethylsilanyloxymethyl)-2,2,6-trimethyl-[1,3]dioxan-4-yl]-hydroxy-methyl-allyl)-2-ethoxyphenyl ester

Synonyms:methanesulfonic acid 3-allyl-4-((R)-1-(S)-[(4S,6S)-4-(tert-butyl-dimethylsilanyloxymethyl)-2,2,6-trimethyl-[1,3]dioxan-4-yl]-hydroxy-methyl-allyl)-2-ethoxyphenyl ester

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Chemical Property of methanesulfonic acid 3-allyl-4-((R)-1-(S)-[(4S,6S)-4-(tert-butyl-dimethylsilanyloxymethyl)-2,2,6-trimethyl-[1,3]dioxan-4-yl]-hydroxy-methyl-allyl)-2-ethoxyphenyl ester

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Technology Process of methanesulfonic acid 3-allyl-4-((R)-1-(S)-[(4S,6S)-4-(tert-butyl-dimethylsilanyloxymethyl)-2,2,6-trimethyl-[1,3]dioxan-4-yl]-hydroxy-methyl-allyl)-2-ethoxyphenyl ester

There total 17 articles about methanesulfonic acid 3-allyl-4-((R)-1-(S)-[(4S,6S)-4-(tert-butyl-dimethylsilanyloxymethyl)-2,2,6-trimethyl-[1,3]dioxan-4-yl]-hydroxy-methyl-allyl)-2-ethoxyphenyl 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: 91.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 695230-92-3
methanesulfonic acid 3-allyl-2-ethoxy-4-(R)-1-[(S)-hydroxy-((4S,6S)-4-hydroxymethyl-2,2,6-trimethyl-[1,3]dioxan-4-yl)methyl]-allyl-phenyl ester

: 805239-95-6
methanesulfonic acid 3-allyl-4-((R)-1-(S)-[(4S,6S)-4-(tert-butyl-dimethylsilanyloxymethyl)-2,2,6-trimethyl-[1,3]dioxan-4-yl]-hydroxy-methyl-allyl)-2-ethoxyphenyl ester

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 23 ℃; for 1h;
DOI:10.1021/ol0480832

Reference yield:

: 805239-89-8
acetic acid 5-formyl-2-methanesulfonyloxy-phenyl ester

: 805239-95-6
methanesulfonic acid 3-allyl-4-((R)-1-(S)-[(4S,6S)-4-(tert-butyl-dimethylsilanyloxymethyl)-2,2,6-trimethyl-[1,3]dioxan-4-yl]-hydroxy-methyl-allyl)-2-ethoxyphenyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: 99 percent / LiCl; DBU / acetonitrile / 0 - 23 °C

2: 86 percent / K₂CO₃ / methanol / 0.1 h / Heating

3: 86 percent / K₂CO₃ / acetone / 3.5 h / Heating

4: 92 percent / various solvent(s) / 7 h / Heating

5: 95 percent / K₂CO₃ / acetone / 3 h / Heating

6: 86 percent / DIBAL-H / CH₂Cl₂ / 1.67 h / -13 - 0 °C

7: 83 percent / LiBr; Ms₂O; Et₃N / tetrahydrofuran / 2.5 h / 0 °C

8: activated Zn / dimethylformamide / 0 - 23 °C

9: 41 percent / TBAF / tetrahydrofuran / 0.5 h / 0 °C

10: 91 percent / imidazole / dimethylformamide / 1 h / 23 °C

With 1H-imidazole; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium chloride; lithium bromide; zinc; Methanesulfonic anhydride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone; acetonitrile; 1: Horner-Wadsworth-Emmons reaction / 4: Claisen rearrangement;
DOI:10.1021/ol0480832

Reference yield:

: 805240-03-3
(E)-3-(3-hydroxy-4-methanesulfonyloxy-phenyl)-acrylic acid methyl ester

: 805239-95-6
methanesulfonic acid 3-allyl-4-((R)-1-(S)-[(4S,6S)-4-(tert-butyl-dimethylsilanyloxymethyl)-2,2,6-trimethyl-[1,3]dioxan-4-yl]-hydroxy-methyl-allyl)-2-ethoxyphenyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 86 percent / K₂CO₃ / acetone / 3.5 h / Heating

2: 92 percent / various solvent(s) / 7 h / Heating

3: 95 percent / K₂CO₃ / acetone / 3 h / Heating

4: 86 percent / DIBAL-H / CH₂Cl₂ / 1.67 h / -13 - 0 °C

5: 83 percent / LiBr; Ms₂O; Et₃N / tetrahydrofuran / 2.5 h / 0 °C

6: activated Zn / dimethylformamide / 0 - 23 °C

7: 41 percent / TBAF / tetrahydrofuran / 0.5 h / 0 °C

8: 91 percent / imidazole / dimethylformamide / 1 h / 23 °C

With 1H-imidazole; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; potassium carbonate; triethylamine; lithium bromide; zinc; Methanesulfonic anhydride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetone; 2: Claisen rearrangement;
DOI:10.1021/ol0480832