(2S,3S,6S,7R,8aR)-5-(3,4-Dimethoxy-benzyloxymethyl)-3-hydroxy-2-((E)-4-iodo-pent-3-enyl)-2,6,7-trimethyl-6-vinyl-2,3,6,7,8,8a-hexahydro-chromen-4-one

Base Information

Chemical Name:(2S,3S,6S,7R,8aR)-5-(3,4-Dimethoxy-benzyloxymethyl)-3-hydroxy-2-((E)-4-iodo-pent-3-enyl)-2,6,7-trimethyl-6-vinyl-2,3,6,7,8,8a-hexahydro-chromen-4-one
CAS No.:501369-26-2
Molecular Formula:C₂₉H₃₉IO₆
Molecular Weight:610.53
Hs Code.:

Synonyms:(2S,3S,6S,7R,8aR)-5-(3,4-Dimethoxy-benzyloxymethyl)-3-hydroxy-2-((E)-4-iodo-pent-3-enyl)-2,6,7-trimethyl-6-vinyl-2,3,6,7,8,8a-hexahydro-chromen-4-one

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Chemical Property of (2S,3S,6S,7R,8aR)-5-(3,4-Dimethoxy-benzyloxymethyl)-3-hydroxy-2-((E)-4-iodo-pent-3-enyl)-2,6,7-trimethyl-6-vinyl-2,3,6,7,8,8a-hexahydro-chromen-4-one

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Technology Process of (2S,3S,6S,7R,8aR)-5-(3,4-Dimethoxy-benzyloxymethyl)-3-hydroxy-2-((E)-4-iodo-pent-3-enyl)-2,6,7-trimethyl-6-vinyl-2,3,6,7,8,8a-hexahydro-chromen-4-one

There total 31 articles about (2S,3S,6S,7R,8aR)-5-(3,4-Dimethoxy-benzyloxymethyl)-3-hydroxy-2-((E)-4-iodo-pent-3-enyl)-2,6,7-trimethyl-6-vinyl-2,3,6,7,8,8a-hexahydro-chromen-4-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:

: 501369-39-7
[(3S,4R,6R)-2-(3,4-Dimethoxy-benzyloxymethyl)-6-hydroxy-3,4-dimethyl-3-vinyl-cyclohex-1-enyl]-[(2S,3R)-3-((E)-4-iodo-pent-3-enyl)-3-methyl-oxiranyl]-methanone

: 501369-26-2
(2S,3S,6S,7R,8aR)-5-(3,4-Dimethoxy-benzyloxymethyl)-3-hydroxy-2-((E)-4-iodo-pent-3-enyl)-2,6,7-trimethyl-6-vinyl-2,3,6,7,8,8a-hexahydro-chromen-4-one

Guidance literature:: With hydrogenchloride; In tert-Amyl alcohol; at 20 ℃; for 2h;
DOI:10.1021/ja0296531

Reference yield:

: 89-82-7,90449-51-7
pulegone

: 501369-26-2
(2S,3S,6S,7R,8aR)-5-(3,4-Dimethoxy-benzyloxymethyl)-3-hydroxy-2-((E)-4-iodo-pent-3-enyl)-2,6,7-trimethyl-6-vinyl-2,3,6,7,8,8a-hexahydro-chromen-4-one

Guidance literature:: Multi-step reaction with 21 steps

1.1: 70 percent / LDA; LiCl

2.1: 75 percent / KOH / Heating

3.1: diisopropyl amine; n-butyllithium; triethylamine / chlorotrimethylsilane / tetrahydrofuran; petroleum ether / -78 - 0 °C

3.2: bromine / tetrahydrofuran; petroleum ether / 2 h / -78 °C

4.1: 5.0 g / lithium carbonate; lithium bromide / dimethylformamide / 4 h / 100 - 105 °C

5.1: diisopropyl amine; n-butyllithium / diethyl ether; petroleum ether / 0.58 h / -78 °C

5.2: diethyl ether; petroleum ether / 1 h / -78 °C

6.1: 378 mg / triethylamine; methanesulfonyl chloride / CH₂Cl₂ / 4 h / 20 °C

7.1: lithium chloride / tetrahydrofuran / 2 h / 20 °C

7.2: n-butyllithium / tetrahydrofuran; petroleum ether / 0.08 h / -78 °C

7.3: 70 percent / tetrahydrofuran; petroleum ether / 0.5 h / -78 °C

8.1: 91 percent / PCC / CH₂Cl₂ / 48 h / 20 °C

9.1: cerium trichloride; sodium borohydride / methanol / 0.5 h / 0 °C

10.1: 173 mg / mCPBA / CH₂Cl₂ / 1 h / 0 °C

11.1: 86 percent / Dess-Martin periodonane; sodium bicarbonate / CH₂Cl₂ / 1 h / 20 °C

12.1: magnesium bromide diethyl etherate / CH₂Cl₂ / 12 h / -78 °C

13.1: 1.0 g / pyridine; trifluoroacetic anhydride; triethylamine / CH₂Cl₂ / 3.5 h / 0 - 20 °C

14.1: magnesium bromide diethyl etherate; butanethiol / diethyl ether / 15 h / 20 °C

14.2: 77 percent / camphorsulfonic acid / CH₂Cl₂ / 18 h / 20 °C

15.1: 94 percent / cerium trichloride; sodium borohydride / methanol / 0.5 h / 0 °C

16.1: triphenylphosphine; diethyl azodicarboxylate; 4-nitrobenzoic acid / tetrahydrofuran / 12 h / 20 °C

16.2: 86 percent / sodium methoxide / methanol / 1 h / 20 °C

17.1: 92 percent / imidazole / dimethylformamide / 2 h / 40 °C

18.1: t-butyllithium / diethyl ether; pentane / 0.5 h / -78 °C

18.2: 51 percent / TMEDA / diethyl ether; pentane / 0.08 h / -78 °C

19.1: 90 percent / Dess-Martin periodinane; sodium bicarbonate / CH₂Cl₂ / 1 h / 20 °C

20.1: TBAF / tetrahydrofuran / 0.5 h / 0 °C

21.1: 25 mg / HCl / 2-methyl-butan-2-ol / 2 h / 20 °C

With pyridine; 1H-imidazole; hydrogenchloride; potassium hydroxide; sodium tetrahydroborate; n-butyllithium; cerium(III) chloride; n-butanethiol; tetrabutyl ammonium fluoride; tert.-butyl lithium; lithium carbonate; sodium hydrogencarbonate; Dess-Martin periodane; magnesium bromide ethyl etherate; methanesulfonyl chloride; triethylamine; diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; pyridinium chlorochromate; trifluoroacetic anhydride; lithium chloride; lithium bromide; lithium diisopropyl amide; diethylazodicarboxylate; 4-nitro-benzoic acid; chloro-trimethyl-silane; In tetrahydrofuran; methanol; tert-Amyl alcohol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; Petroleum ether; pentane; 16.1: Mitsunobu inversion;
DOI:10.1021/ja0296531

Reference yield:

: 234078-11-6
(2RS,3R)-2,3-dimethylcyclohexanone

: 501369-26-2
(2S,3S,6S,7R,8aR)-5-(3,4-Dimethoxy-benzyloxymethyl)-3-hydroxy-2-((E)-4-iodo-pent-3-enyl)-2,6,7-trimethyl-6-vinyl-2,3,6,7,8,8a-hexahydro-chromen-4-one

Guidance literature:: Multi-step reaction with 19 steps

1.1: diisopropyl amine; n-butyllithium; triethylamine / chlorotrimethylsilane / tetrahydrofuran; petroleum ether / -78 - 0 °C

1.2: bromine / tetrahydrofuran; petroleum ether / 2 h / -78 °C

2.1: 5.0 g / lithium carbonate; lithium bromide / dimethylformamide / 4 h / 100 - 105 °C

3.1: diisopropyl amine; n-butyllithium / diethyl ether; petroleum ether / 0.58 h / -78 °C

3.2: diethyl ether; petroleum ether / 1 h / -78 °C

4.1: 378 mg / triethylamine; methanesulfonyl chloride / CH₂Cl₂ / 4 h / 20 °C

5.1: lithium chloride / tetrahydrofuran / 2 h / 20 °C

5.2: n-butyllithium / tetrahydrofuran; petroleum ether / 0.08 h / -78 °C

5.3: 70 percent / tetrahydrofuran; petroleum ether / 0.5 h / -78 °C

6.1: 91 percent / PCC / CH₂Cl₂ / 48 h / 20 °C

7.1: cerium trichloride; sodium borohydride / methanol / 0.5 h / 0 °C

8.1: 173 mg / mCPBA / CH₂Cl₂ / 1 h / 0 °C

9.1: 86 percent / Dess-Martin periodonane; sodium bicarbonate / CH₂Cl₂ / 1 h / 20 °C

10.1: magnesium bromide diethyl etherate / CH₂Cl₂ / 12 h / -78 °C

11.1: 1.0 g / pyridine; trifluoroacetic anhydride; triethylamine / CH₂Cl₂ / 3.5 h / 0 - 20 °C

12.1: magnesium bromide diethyl etherate; butanethiol / diethyl ether / 15 h / 20 °C

12.2: 77 percent / camphorsulfonic acid / CH₂Cl₂ / 18 h / 20 °C

13.1: 94 percent / cerium trichloride; sodium borohydride / methanol / 0.5 h / 0 °C

14.1: triphenylphosphine; diethyl azodicarboxylate; 4-nitrobenzoic acid / tetrahydrofuran / 12 h / 20 °C

14.2: 86 percent / sodium methoxide / methanol / 1 h / 20 °C

15.1: 92 percent / imidazole / dimethylformamide / 2 h / 40 °C

16.1: t-butyllithium / diethyl ether; pentane / 0.5 h / -78 °C

16.2: 51 percent / TMEDA / diethyl ether; pentane / 0.08 h / -78 °C

17.1: 90 percent / Dess-Martin periodinane; sodium bicarbonate / CH₂Cl₂ / 1 h / 20 °C

18.1: TBAF / tetrahydrofuran / 0.5 h / 0 °C

19.1: 25 mg / HCl / 2-methyl-butan-2-ol / 2 h / 20 °C

With pyridine; 1H-imidazole; hydrogenchloride; sodium tetrahydroborate; n-butyllithium; cerium(III) chloride; n-butanethiol; tetrabutyl ammonium fluoride; tert.-butyl lithium; lithium carbonate; sodium hydrogencarbonate; Dess-Martin periodane; magnesium bromide ethyl etherate; methanesulfonyl chloride; triethylamine; diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; pyridinium chlorochromate; trifluoroacetic anhydride; lithium chloride; lithium bromide; diethylazodicarboxylate; 4-nitro-benzoic acid; chloro-trimethyl-silane; In tetrahydrofuran; methanol; tert-Amyl alcohol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; Petroleum ether; pentane; 14.1: Mitsunobu inversion;
DOI:10.1021/ja0296531