(S)-1-{(1R,2R,6R)-6-isopropyl-2-[(2S,3R)-2-methoxymethoxy-3-(4-methoxyphenoxy)-pent-4-enyl]-3-methyl-cyclohex-3-enyl}-pent-4-en-2-ol

Base Information

• Chemical Name: (S)-1-{(1R,2R,6R)-6-isopropyl-2-[(2S,3R)-2-methoxymethoxy-3-(4-methoxyphenoxy)-pent-4-enyl]-3-methyl-cyclohex-3-enyl}-pent-4-en-2-ol
• CAS No.: 849122-84-5
• Molecular Formula: C₂₉H₄₄O₅
• Molecular Weight: 472.665

Synonyms:(S)-1-{(1R,2R,6R)-6-isopropyl-2-[(2S,3R)-2-methoxymethoxy-3-(4-methoxyphenoxy)-pent-4-enyl]-3-methyl-cyclohex-3-enyl}-pent-4-en-2-ol

Chemical Property of (S)-1-{(1R,2R,6R)-6-isopropyl-2-[(2S,3R)-2-methoxymethoxy-3-(4-methoxyphenoxy)-pent-4-enyl]-3-methyl-cyclohex-3-enyl}-pent-4-en-2-ol

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Technology Process of (S)-1-{(1R,2R,6R)-6-isopropyl-2-[(2S,3R)-2-methoxymethoxy-3-(4-methoxyphenoxy)-pent-4-enyl]-3-methyl-cyclohex-3-enyl}-pent-4-en-2-ol

There total 10 articles about (S)-1-{(1R,2R,6R)-6-isopropyl-2-[(2S,3R)-2-methoxymethoxy-3-(4-methoxyphenoxy)-pent-4-enyl]-3-methyl-cyclohex-3-enyl}-pent-4-en-2-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: 87.0%

{(1R,2R,6R)-6-isopropyl-2-[(2S,3R)-2-methoxymethoxy-3-(4-methoxyphenoxy)-pent-4-enyl]-3-methyl-cyclohex-3-enyl}-acetaldehyde (848760-91-8) + allylmagnesium bromide (1730-25-2) → (S)-1-{(1R,2R,6R)-6-isopropyl-2-[(2S,3R)-2-methoxymethoxy-3-(4-methoxyphenoxy)-pent-4-enyl]-3-methyl-cyclohex-3-enyl}-pent-4-en-2-ol (849122-84-5)

Guidance literature:

allylmagnesium bromide; With (R,R)-taddol(cyclopentadienyl)TiCl; In diethyl ether; at 0 ℃; for 1.5h;

{(1R,2R,6R)-6-isopropyl-2-[(2S,3R)-2-methoxymethoxy-3-(4-methoxyphenoxy)-pent-4-enyl]-3-methyl-cyclohex-3-enyl}-acetaldehyde; In diethyl ether; at -78 ℃; for 3h;

DOI:10.1016/j.tet.2004.12.039

Reference yield:

(1R,2R,6R)-6-isopropyl-2-[(2S,3R)-2-methoxymethoxy-3-(4-methoxyphenoxy)-pent-4-enyl]-3-methyl-cyclohex-3-enecarbaldehyde (849122-81-2) → (S)-1-{(1R,2R,6R)-6-isopropyl-2-[(2S,3R)-2-methoxymethoxy-3-(4-methoxyphenoxy)-pent-4-enyl]-3-methyl-cyclohex-3-enyl}-pent-4-en-2-ol (849122-84-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 408 mg / NaBH₄ / ethanol / 0.33 h / 25 °C

2: 95 percent / TEA / CH₂Cl₂ / 0 - 25 °C

3: 100 percent / 18-crown-6 / acetonitrile / 2.5 h / 80 °C

4: DIBAL-H / hexane; toluene / 1 h / -78 °C

5: 420 mg / tetrahydrofuran; diethyl ether / 48 h / -78 °C

With sodium tetrahydroborate; 18-crown-6 ether; TEA; diisobutylaluminium hydride; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; toluene; acetonitrile; 5: Brown allylation;

DOI:10.1016/j.tet.2004.12.039

Reference yield:

(2S,3R)-1-[(1R,5R,6R)-6-dimethoxymethyl-5-isopropyl-2-methyl-cyclohex-2-enyl]3-(4-methoxyphenoxy)-pent-4-en-2-ol (848760-88-3) → (S)-1-{(1R,2R,6R)-6-isopropyl-2-[(2S,3R)-2-methoxymethoxy-3-(4-methoxyphenoxy)-pent-4-enyl]-3-methyl-cyclohex-3-enyl}-pent-4-en-2-ol (849122-84-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 95 percent / DIPEA; TBAI / CH₂Cl₂ / 7 h / 25 °C

2: LiBF₄ / acetonitrile; H₂O / 6 h / 25 °C

3: 408 mg / NaBH₄ / ethanol / 0.33 h / 25 °C

4: 95 percent / TEA / CH₂Cl₂ / 0 - 25 °C

5: 100 percent / 18-crown-6 / acetonitrile / 2.5 h / 80 °C

6: DIBAL-H / hexane; toluene / 1 h / -78 °C

7: 420 mg / tetrahydrofuran; diethyl ether / 48 h / -78 °C

With sodium tetrahydroborate; lithium tetrafluoroborate; 18-crown-6 ether; TEA; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; water; toluene; acetonitrile; 7: Brown allylation;

DOI:10.1016/j.tet.2004.12.039

upstream raw materials:

{(1R,2R,6R)-6-isopropyl-2-[(2S,3R)-2-methoxymethoxy-3-(4-methoxyphenoxy)-pent-4-enyl]-3-methyl-cyclohex-3-enyl}-acetaldehyde

B-allyldiisopinocampheylborane

allylmagnesium bromide

(2S,3R)-1-[(1R,5R,6R)-6-dimethoxymethyl-5-isopropyl-2-methyl-cyclohex-2-enyl]3-(4-methoxyphenoxy)-pent-4-en-2-ol

Downstream raw materials:

(E)-3-(1-methyl-1H-imidazol-4-yl)-acrylic acid (Z)-(1R,4aR,6S,7R,11S,12aR)-11-(tert-butyl-diphenylsilanyloxy)-1-isopropyl-7-(4-methoxyphenoxy)-4-methyl-1,2,4a,5,6,7,10,11,12,12a-decahydro-benzocyclodecen-6-yl ester

(Z)-(1R,4aR,6S,7R,11S,12aR)-11-(tert-butyl-diphenylsilanyloxy)-1-isopropyl-7-(4-methoxyphenoxy)-4-methyl-1,2,4a,5,6,7,10,11,12,12a-decahydro-benzocyclodecen-6-ol

2,2-dimethyl-propionic acid (1S,2R)-1-{(1R,5R,6R)-6-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-pent-4-enyl]-5-isopropyl-2-methyl-cyclohex-2-enylmethyl}-2-hydroxy-but-3-enyl ester

(2S,3R)-1-{(1R,5R,6R)-6-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-pent-4-enyl]-5-isopropyl-2-methyl-cyclohex-2-enyl}-3-(4-methoxyphenoxy)-pent-4-en-2-ol

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