(Z)-2-Hydroxymethyl-3-[(1S,2R,6R)-6-isopropyl-3-methyl-2-((2S,3S)-3-methyl-2,3-bis-triethylsilanyloxy-pent-4-ynyl)-cyclohex-3-enyl]-propenal

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Chemical Name:(Z)-2-Hydroxymethyl-3-[(1S,2R,6R)-6-isopropyl-3-methyl-2-((2S,3S)-3-methyl-2,3-bis-triethylsilanyloxy-pent-4-ynyl)-cyclohex-3-enyl]-propenal
CAS No.:201142-44-1
Molecular Formula:C₃₂H₅₈O₄Si₂
Molecular Weight:562.981
Hs Code.:

Synonyms:(Z)-2-Hydroxymethyl-3-[(1S,2R,6R)-6-isopropyl-3-methyl-2-((2S,3S)-3-methyl-2,3-bis-triethylsilanyloxy-pent-4-ynyl)-cyclohex-3-enyl]-propenal

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Chemical Property of (Z)-2-Hydroxymethyl-3-[(1S,2R,6R)-6-isopropyl-3-methyl-2-((2S,3S)-3-methyl-2,3-bis-triethylsilanyloxy-pent-4-ynyl)-cyclohex-3-enyl]-propenal

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Technology Process of (Z)-2-Hydroxymethyl-3-[(1S,2R,6R)-6-isopropyl-3-methyl-2-((2S,3S)-3-methyl-2,3-bis-triethylsilanyloxy-pent-4-ynyl)-cyclohex-3-enyl]-propenal

There total 18 articles about (Z)-2-Hydroxymethyl-3-[(1S,2R,6R)-6-isopropyl-3-methyl-2-((2S,3S)-3-methyl-2,3-bis-triethylsilanyloxy-pent-4-ynyl)-cyclohex-3-enyl]-propenal 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: 90.0%

: 201142-42-9
(E)-2-Cyano-3-[(1S,2R,6R)-6-isopropyl-3-methyl-2-((2S,3S)-3-methyl-2,3-bis-triethylsilanyloxy-pent-4-ynyl)-cyclohex-3-enyl]-acrylic acid ethyl ester

: 201142-44-1
(Z)-2-Hydroxymethyl-3-[(1S,2R,6R)-6-isopropyl-3-methyl-2-((2S,3S)-3-methyl-2,3-bis-triethylsilanyloxy-pent-4-ynyl)-cyclohex-3-enyl]-propenal

Guidance literature:: With diisobutylaluminium hydride; In hexane; toluene; at -78 - -10 ℃; for 8h;
DOI:10.1021/ja981062g

Reference yield:

: 2244-16-8,6485-40-1
(S)-p-mentha-6,8-dien-2-one

: 201142-44-1
(Z)-2-Hydroxymethyl-3-[(1S,2R,6R)-6-isopropyl-3-methyl-2-((2S,3S)-3-methyl-2,3-bis-triethylsilanyloxy-pent-4-ynyl)-cyclohex-3-enyl]-propenal

Guidance literature:: Multi-step reaction with 17 steps

1: H₂O₂, NaOH / methanol / 2 h / 0 °C

2: H₂ / PtO₂ / ethanol / 12 h / 25 °C

3: 1.) LDA / 2.) THF, from -78 to 0 deg C, 2 h

4: Et₃N / CH₂Cl₂ / 12 h

5: 93 percent / L-selectride / tetrahydrofuran / 2 h / -78 °C

6: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

7: sodium naphthalenide / tetrahydrofuran / 0.5 h / 0 °C

8: 74 percent / propionic acid / 72 h / 170 °C

9: 97 percent / DIBAL / CH₂Cl₂ / 0.5 h / -78 °C

10: 1.) t-BuLi, 3.) conc. H₂SO₄

11: tetrahydrofuran / 6 h / -78 °C

12: 100 percent / TBAF / tetrahydrofuran / 1 h / 0 - 25 °C

13: 100 percent / Et₃N / CH₂Cl₂ / 2 h / 25 °C

14: 98 percent / PPTS, MeOH / CH₂Cl₂ / 0.75 h / 25 °C

15: 98 percent / tetra-n-propylammonium perruthenate, NMO, mol. sieves 4A / CH₂Cl₂ / 0.5 h / 25 °C

16: 95 percent / β-alanine / ethanol / 72 h / 50 °C

17: 90 percent / DIBAL / hexane; toluene / 8 h / -78 - -10 °C

With methanol; sodium hydroxide; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; sulfuric acid; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; tert.-butyl lithium; pyridinium p-toluenesulfonate; L-Selectride; sodium naphthalenide; diisobutylaluminium hydride; propionic acid; triethylamine; lithium diisopropyl amide; 3-amino propanoic acid; platinum(IV) oxide; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; toluene;
DOI:10.1021/ja981062g

Reference yield:

: 39903-97-4
(S)-carvone oxide

: 201142-44-1
(Z)-2-Hydroxymethyl-3-[(1S,2R,6R)-6-isopropyl-3-methyl-2-((2S,3S)-3-methyl-2,3-bis-triethylsilanyloxy-pent-4-ynyl)-cyclohex-3-enyl]-propenal

Guidance literature:: Multi-step reaction with 16 steps

1: H₂ / PtO₂ / ethanol / 12 h / 25 °C

2: 1.) LDA / 2.) THF, from -78 to 0 deg C, 2 h

3: Et₃N / CH₂Cl₂ / 12 h

4: 93 percent / L-selectride / tetrahydrofuran / 2 h / -78 °C

5: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

6: sodium naphthalenide / tetrahydrofuran / 0.5 h / 0 °C

7: 74 percent / propionic acid / 72 h / 170 °C

8: 97 percent / DIBAL / CH₂Cl₂ / 0.5 h / -78 °C

9: 1.) t-BuLi, 3.) conc. H₂SO₄

10: tetrahydrofuran / 6 h / -78 °C

11: 100 percent / TBAF / tetrahydrofuran / 1 h / 0 - 25 °C

12: 100 percent / Et₃N / CH₂Cl₂ / 2 h / 25 °C

13: 98 percent / PPTS, MeOH / CH₂Cl₂ / 0.75 h / 25 °C

14: 98 percent / tetra-n-propylammonium perruthenate, NMO, mol. sieves 4A / CH₂Cl₂ / 0.5 h / 25 °C

15: 95 percent / β-alanine / ethanol / 72 h / 50 °C

16: 90 percent / DIBAL / hexane; toluene / 8 h / -78 - -10 °C

With methanol; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; sulfuric acid; tetrabutyl ammonium fluoride; hydrogen; tert.-butyl lithium; pyridinium p-toluenesulfonate; L-Selectride; sodium naphthalenide; diisobutylaluminium hydride; propionic acid; triethylamine; lithium diisopropyl amide; 3-amino propanoic acid; platinum(IV) oxide; In tetrahydrofuran; ethanol; hexane; dichloromethane; toluene;
DOI:10.1021/ja981062g