methanesulfonic acid 3-allyl-2-ethoxy-4-(R)-1-[(2S,4S,5S)-5-hydroxymethyl-5-((S)-2-hydroxy-propyl)-2-phenyl-[1,3]dioxolan-4-yl]-allyl-phenyl ester

Base Information

Chemical Name:methanesulfonic acid 3-allyl-2-ethoxy-4-(R)-1-[(2S,4S,5S)-5-hydroxymethyl-5-((S)-2-hydroxy-propyl)-2-phenyl-[1,3]dioxolan-4-yl]-allyl-phenyl ester
CAS No.:695230-84-3
Molecular Formula:C₂₈H₃₆O₈S
Molecular Weight:532.655
Hs Code.:

Synonyms:methanesulfonic acid 3-allyl-2-ethoxy-4-(R)-1-[(2S,4S,5S)-5-hydroxymethyl-5-((S)-2-hydroxy-propyl)-2-phenyl-[1,3]dioxolan-4-yl]-allyl-phenyl ester

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Chemical Property of methanesulfonic acid 3-allyl-2-ethoxy-4-(R)-1-[(2S,4S,5S)-5-hydroxymethyl-5-((S)-2-hydroxy-propyl)-2-phenyl-[1,3]dioxolan-4-yl]-allyl-phenyl ester

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Technology Process of methanesulfonic acid 3-allyl-2-ethoxy-4-(R)-1-[(2S,4S,5S)-5-hydroxymethyl-5-((S)-2-hydroxy-propyl)-2-phenyl-[1,3]dioxolan-4-yl]-allyl-phenyl ester

There total 18 articles about methanesulfonic acid 3-allyl-2-ethoxy-4-(R)-1-[(2S,4S,5S)-5-hydroxymethyl-5-((S)-2-hydroxy-propyl)-2-phenyl-[1,3]dioxolan-4-yl]-allyl-phenyl 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: 78.0%

: 805239-97-8
Methanesulfonic acid 3-allyl-2-ethoxy-4-[(R)-1-((2S,4S,5S,10S)-8,8,10-trimethyl-2-phenyl-1,3,7,9-tetraoxa-spiro[4.6]undec-4-yl)-allyl]-phenyl ester

: 695230-84-3
methanesulfonic acid 3-allyl-2-ethoxy-4-(R)-1-[(2S,4S,5S)-5-hydroxymethyl-5-((S)-2-hydroxy-propyl)-2-phenyl-[1,3]dioxolan-4-yl]-allyl-phenyl ester

Guidance literature:: With p-toluenesulfonic acid monohydrate; In methanol; at 25 ℃; for 2.5h;
DOI:10.1021/ol0480832

Reference yield:

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

: 695230-84-3
methanesulfonic acid 3-allyl-2-ethoxy-4-(R)-1-[(2S,4S,5S)-5-hydroxymethyl-5-((S)-2-hydroxy-propyl)-2-phenyl-[1,3]dioxolan-4-yl]-allyl-phenyl ester

Guidance literature:: Multi-step reaction with 11 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: 66 percent / CSA / toluene / 0.33 h / 25 °C / 22.5 Torr

11: 78 percent / 4-toluenesulfonic acid hydrate / methanol / 2.5 h / 25 °C

With camphor-10-sulfonic acid; p-toluenesulfonic acid monohydrate; 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; toluene; 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

: 695230-84-3
methanesulfonic acid 3-allyl-2-ethoxy-4-(R)-1-[(2S,4S,5S)-5-hydroxymethyl-5-((S)-2-hydroxy-propyl)-2-phenyl-[1,3]dioxolan-4-yl]-allyl-phenyl ester

Guidance literature:: Multi-step reaction with 9 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: 66 percent / CSA / toluene / 0.33 h / 25 °C / 22.5 Torr

9: 78 percent / 4-toluenesulfonic acid hydrate / methanol / 2.5 h / 25 °C

With camphor-10-sulfonic acid; p-toluenesulfonic acid monohydrate; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; potassium carbonate; triethylamine; lithium bromide; zinc; Methanesulfonic anhydride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; 2: Claisen rearrangement;
DOI:10.1021/ol0480832