(1S,5R,9R,10R,11R,12R,13S)-13-hydroxy-1,9-dimethoxy-5-[(4-methoxyphenyl)methoxymethyl]-7,10,12-trimethyl-4,15-dioxabicyclo[9.3.1]pentadec-7-en-3-one

Base Information

Chemical Name:(1S,5R,9R,10R,11R,12R,13S)-13-hydroxy-1,9-dimethoxy-5-[(4-methoxyphenyl)methoxymethyl]-7,10,12-trimethyl-4,15-dioxabicyclo[9.3.1]pentadec-7-en-3-one
CAS No.:439143-48-3
Molecular Formula:C₂₇H₄₀O₈
Molecular Weight:492.61
Hs Code.:

(1S,5R,9R,10R,11R,12R,13S)-13-hydroxy-1,9-dimethoxy-5-[(4-methoxyphenyl)methoxymethyl]-7,10,12-trimethyl-4,15-dioxabicyclo[9.3.1]pentadec-7-en-3-one

Synonyms:(1S,5R,9R,10R,11R,12R,13S)-13-hydroxy-1,9-dimethoxy-5-[(4-methoxyphenyl)methoxymethyl]-7,10,12-trimethyl-4,15-dioxabicyclo[9.3.1]pentadec-7-en-3-one

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Chemical Property of (1S,5R,9R,10R,11R,12R,13S)-13-hydroxy-1,9-dimethoxy-5-[(4-methoxyphenyl)methoxymethyl]-7,10,12-trimethyl-4,15-dioxabicyclo[9.3.1]pentadec-7-en-3-one

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Technology Process of (1S,5R,9R,10R,11R,12R,13S)-13-hydroxy-1,9-dimethoxy-5-[(4-methoxyphenyl)methoxymethyl]-7,10,12-trimethyl-4,15-dioxabicyclo[9.3.1]pentadec-7-en-3-one

There total 16 articles about (1S,5R,9R,10R,11R,12R,13S)-13-hydroxy-1,9-dimethoxy-5-[(4-methoxyphenyl)methoxymethyl]-7,10,12-trimethyl-4,15-dioxabicyclo[9.3.1]pentadec-7-en-3-one 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: 99.0%

: 439143-60-9
(1S,11S,12S,13S,5R,9R,10R)-1,9-dimethoxy-5-[(4-methoxyphenyl)methoxy]-7,10,12-trimethyl-4,15-dioxa-13-(1,1,2,2-tetramethyl-1-silaproxy)bicyclo[9.3.1]pentadec-7-en-3-one

: 439143-48-3
(1S,5R,9R,10R,11R,12R,13S)-13-hydroxy-1,9-dimethoxy-5-[(4-methoxyphenyl)methoxymethyl]-7,10,12-trimethyl-4,15-dioxabicyclo[9.3.1]pentadec-7-en-3-one

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 8h;
DOI:10.1016/j.tet.2008.02.001

Reference yield:

: 101712-01-0
(S)-1-((S)-4-benzyl-2-oxo-oxazolidin-3-yl)-2-methylpentane-1,3-dione

: 439143-48-3
(1S,5R,9R,10R,11R,12R,13S)-13-hydroxy-1,9-dimethoxy-5-[(4-methoxyphenyl)methoxymethyl]-7,10,12-trimethyl-4,15-dioxabicyclo[9.3.1]pentadec-7-en-3-one

Guidance literature:: Multi-step reaction with 15 steps

1.1: Cy₂BCl; Et₃NMe₂ / diethyl ether / 0 °C

1.2: diethyl ether / -78 - -20 °C

2.1: Me₄NBH(OAc)3; AcOH / acetonitrile / 0 °C

3.1: HN(CH₂CH₂OH)2 / ethyl acetate / 20 °C

4.1: AlMe₃ / CH₂Cl₂ / 0 - 20 °C

5.1: PPTS / acetone / 20 °C

6.1: LiAlH₄ / diethyl ether / 20 °C

7.1: BF₃*OEt₂ / toluene / -90 °C

8.1: 2,6-lutidine / CH₂Cl₂ / -78 °C

9.1: PPTS / 20 °C

10.1: 2,6-di-tert-butylpyridine / CH₂Cl₂ / 20 °C

11.1: TBAF / tetrahydrofuran / 20 °C

12.1: Et₃N; DMAP / CH₂Cl₂ / 0 °C

13.1: LiOH; H₂O / methanol; tetrahydrofuran / 20 °C

14.1: 1.5 mM Cs₂CO₃; 18-crown-6 / toluene / 110 °C

15.1: TBAF / tetrahydrofuran / 20 °C

With 2,6-dimethylpyridine; dmap; lithium hydroxide; lithium aluminium tetrahydride; 2,6-di-tert-butyl-pyridine; 18-crown-6 ether; boron trifluoride diethyl etherate; dicyclohexylboron chloride; tetrabutyl ammonium fluoride; water; trimethylaluminum; pyridinium p-toluenesulfonate; caesium carbonate; acetic acid; triethylamine; 2,2'-iminobis[ethanol]; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; ethyl acetate; acetone; toluene; acetonitrile;
DOI:10.1021/ja026235n

Reference yield:

: 439143-54-1
(2E)(5S)-6-[(4-methoxyphenyl)methoxy]-3-methyl-5-(tert-butyldimethylsilyloxy)hex-2-enal

: 439143-48-3
(1S,5R,9R,10R,11R,12R,13S)-13-hydroxy-1,9-dimethoxy-5-[(4-methoxyphenyl)methoxymethyl]-7,10,12-trimethyl-4,15-dioxabicyclo[9.3.1]pentadec-7-en-3-one

Guidance literature:: Multi-step reaction with 15 steps

1.1: Cy₂BCl; Et₃NMe₂ / diethyl ether / 0 °C

1.2: diethyl ether / -78 - -20 °C

2.1: Me₄NBH(OAc)3; AcOH / acetonitrile / 0 °C

3.1: HN(CH₂CH₂OH)2 / ethyl acetate / 20 °C

4.1: AlMe₃ / CH₂Cl₂ / 0 - 20 °C

5.1: PPTS / acetone / 20 °C

6.1: LiAlH₄ / diethyl ether / 20 °C

7.1: BF₃*OEt₂ / toluene / -90 °C

8.1: 2,6-lutidine / CH₂Cl₂ / -78 °C

9.1: PPTS / 20 °C

10.1: 2,6-di-tert-butylpyridine / CH₂Cl₂ / 20 °C

11.1: TBAF / tetrahydrofuran / 20 °C

12.1: Et₃N; DMAP / CH₂Cl₂ / 0 °C

13.1: LiOH; H₂O / methanol; tetrahydrofuran / 20 °C

14.1: 1.5 mM Cs₂CO₃; 18-crown-6 / toluene / 110 °C

15.1: TBAF / tetrahydrofuran / 20 °C

With 2,6-dimethylpyridine; dmap; lithium hydroxide; lithium aluminium tetrahydride; 2,6-di-tert-butyl-pyridine; 18-crown-6 ether; boron trifluoride diethyl etherate; dicyclohexylboron chloride; tetrabutyl ammonium fluoride; water; trimethylaluminum; pyridinium p-toluenesulfonate; caesium carbonate; acetic acid; triethylamine; 2,2'-iminobis[ethanol]; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; ethyl acetate; acetone; toluene; acetonitrile;
DOI:10.1021/ja026235n