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

Base Information

• Chemical Name: 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
• CAS No.: 805239-97-8
• Molecular Formula: C₃₁H₄₀O₈S
• Molecular Weight: 572.72

Synonyms: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

Chemical Property of 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

Chemical Property:

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Technology Process of 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

There total 17 articles about 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 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: 66.0%

benzaldehyde dimethyl acetal (1125-88-8) + 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 (695230-92-3) → 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 (805239-97-8)

Guidance literature:

With camphor-10-sulfonic acid; In toluene; at 25 ℃; for 0.333333h; under 22.5018 Torr;

DOI:10.1021/ol0480832

Reference yield:

acetic acid 5-formyl-2-methanesulfonyloxy-phenyl ester (805239-89-8) → 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 (805239-97-8)

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: 66 percent / CSA / toluene / 0.33 h / 25 °C / 22.5 Torr

With camphor-10-sulfonic acid; 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:

(E)-3-(3-hydroxy-4-methanesulfonyloxy-phenyl)-acrylic acid methyl ester (805240-03-3) → 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 (805239-97-8)

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: 66 percent / CSA / toluene / 0.33 h / 25 °C / 22.5 Torr

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

DOI:10.1021/ol0480832

upstream raw materials:

benzaldehyde dimethyl acetal

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

acetic acid 5-formyl-2-methanesulfonyloxy-phenyl ester

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

Downstream raw materials:

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-phenol

C₄₁H₄₂O₈

C₄₉H₄₄F₆O₁₀S

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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