(1S,2R,5R,6S)-2-(3,4-methylenedioxy)phenyl-6-(4-methanesulfonyloxy-3-methoxy)phenyl-3,7-dioxabicyclo[3.3.0]octan-8-ol

Base Information

Chemical Name:(1S,2R,5R,6S)-2-(3,4-methylenedioxy)phenyl-6-(4-methanesulfonyloxy-3-methoxy)phenyl-3,7-dioxabicyclo[3.3.0]octan-8-ol
CAS No.:651779-92-9
Molecular Formula:C₂₁H₂₂O₉S
Molecular Weight:450.466
Hs Code.:

Synonyms:(1S,2R,5R,6S)-2-(3,4-methylenedioxy)phenyl-6-(4-methanesulfonyloxy-3-methoxy)phenyl-3,7-dioxabicyclo[3.3.0]octan-8-ol

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Chemical Property of (1S,2R,5R,6S)-2-(3,4-methylenedioxy)phenyl-6-(4-methanesulfonyloxy-3-methoxy)phenyl-3,7-dioxabicyclo[3.3.0]octan-8-ol

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Technology Process of (1S,2R,5R,6S)-2-(3,4-methylenedioxy)phenyl-6-(4-methanesulfonyloxy-3-methoxy)phenyl-3,7-dioxabicyclo[3.3.0]octan-8-ol

There total 8 articles about (1S,2R,5R,6S)-2-(3,4-methylenedioxy)phenyl-6-(4-methanesulfonyloxy-3-methoxy)phenyl-3,7-dioxabicyclo[3.3.0]octan-8-ol 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: 74.0%

: 651779-90-7
(1S,2R,5R,6S)-2-(3,4-methylenedioxy)phenyl-6-(4-methanesulfonyloxy-3-methoxy)phenyl-3,7-dioxabicyclo[3.3.0]octan-8-one

: 651779-92-9
(1S,2R,5R,6S)-2-(3,4-methylenedioxy)phenyl-6-(4-methanesulfonyloxy-3-methoxy)phenyl-3,7-dioxabicyclo[3.3.0]octan-8-ol

: (2R,3R,4S)-2-[(3,4-methylenedioxy)phenyl]-3-hydroxymethyl-4-{[(4-methanesulfonyloxy-3-methoxy)phenyl](hydroxy)methyl}tetrahydrofuran

Guidance literature:: With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃; for 0.333333h;
DOI:10.1021/jo035365r

Reference yield:

: 52200-05-2
4-methanesulfonyloxy-3-methoxybenzaldehyde

: 651779-92-9
(1S,2R,5R,6S)-2-(3,4-methylenedioxy)phenyl-6-(4-methanesulfonyloxy-3-methoxy)phenyl-3,7-dioxabicyclo[3.3.0]octan-8-ol

Guidance literature:: Multi-step reaction with 8 steps

1: tetrahydrofuran / -60 - -10 °C

2: 39 percent / Novozyme 435 / 17 h / 40 °C

3: 92 percent / xylene / 0.25 h / 150 °C

4: Mn(OAc)3*2H₂O; Cu(OAc)2; KOAc / acetic acid / 0.25 h / 70 °C

5: 54 percent / 2,6-di-tert-butylpyridine; Mg(ClO₄)2 / 2.5 h / 120 °C

6: 88 percent / triflic anhydride; tetrabutylammonium bromide; sodium azide / sodium hydroxide / hexane; acetonitrile; H₂O / 0.5 h / 0 °C

7: 83 percent / dirhodium tetraacetate / CH₂Cl₂ / 3 h / 20 °C

8: 13 percent / LiAlH₄ / tetrahydrofuran / 0.33 h / 0 °C

With dirhodium tetraacetate; lithium aluminium tetrahydride; sodium azide; 2,6-di-tert-butyl-pyridine; magnesium(II) perchlorate; copper diacetate; novozyme 435; trifluoromethylsulfonic anhydride; tetrabutylammomium bromide; potassium acetate; manganese triacetate; sodium hydroxide; In tetrahydrofuran; hexane; dichloromethane; water; acetic acid; acetonitrile; xylene;
DOI:10.1021/jo035365r

Reference yield:

: 651779-84-9
1-(4-methanesulfonyloxy-3-methoxyphenyl)prop-2-en-1-ol

: 651779-92-9
(1S,2R,5R,6S)-2-(3,4-methylenedioxy)phenyl-6-(4-methanesulfonyloxy-3-methoxy)phenyl-3,7-dioxabicyclo[3.3.0]octan-8-ol

Guidance literature:: Multi-step reaction with 7 steps

1: 39 percent / Novozyme 435 / 17 h / 40 °C

2: 92 percent / xylene / 0.25 h / 150 °C

3: Mn(OAc)3*2H₂O; Cu(OAc)2; KOAc / acetic acid / 0.25 h / 70 °C

4: 54 percent / 2,6-di-tert-butylpyridine; Mg(ClO₄)2 / 2.5 h / 120 °C

5: 88 percent / triflic anhydride; tetrabutylammonium bromide; sodium azide / sodium hydroxide / hexane; acetonitrile; H₂O / 0.5 h / 0 °C

6: 83 percent / dirhodium tetraacetate / CH₂Cl₂ / 3 h / 20 °C

7: 13 percent / LiAlH₄ / tetrahydrofuran / 0.33 h / 0 °C

With dirhodium tetraacetate; lithium aluminium tetrahydride; sodium azide; 2,6-di-tert-butyl-pyridine; magnesium(II) perchlorate; copper diacetate; novozyme 435; trifluoromethylsulfonic anhydride; tetrabutylammomium bromide; potassium acetate; manganese triacetate; sodium hydroxide; In tetrahydrofuran; hexane; dichloromethane; water; acetic acid; acetonitrile; xylene;
DOI:10.1021/jo035365r