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

Base Information

Chemical Name: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
CAS No.:695230-92-3
Molecular Formula:C₂₄H₃₆O₈S
Molecular Weight:484.611
Hs Code.:

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 17 articles about 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 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: 41.0%

: Methanesulfonic acid 3-allyl-4-(1-{[(4S,6S)-4-(tert-butyl-dimethyl-silanyloxymethyl)-2,2,6-trimethyl-[1,3]dioxan-4-yl]-hydroxy-methyl}-allyl)-2-ethoxy-phenyl ester

: 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

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

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 0.5h;
DOI:10.1021/ol0480832

Reference yield: 41.0%

: 695230-89-8
(4S,6S)-4-(tert-butyl-dimethyl-silanyloxymethyl)-2,2,6-trimethyl-[1,3]dioxane-4-carbaldehyde

: Methanesulfonic acid 3-allyl-4-((E)-3-bromo-allyl)-2-ethoxy-phenyl ester

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

Guidance literature:: (4S,6S)-4-(tert-butyl-dimethyl-silanyloxymethyl)-2,2,6-trimethyl-[1,3]dioxane-4-carbaldehyde; Methanesulfonic acid 3-allyl-4-((E)-3-bromo-allyl)-2-ethoxy-phenyl ester; With zinc; In N,N-dimethyl-formamide; at 0 - 23 ℃;

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 0.5h;
DOI:10.1021/ol049514j

Reference yield:

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

: 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

Guidance literature:: Multi-step reaction with 9 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

With 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