(Z)-(2S,3S,9R)-3-(tert-Butyl-diphenyl-silanyloxy)-9-((E)-2-methyl-buta-1,3-dienyl)-2,3,4,7,8,9-hexahydro-oxonine-2-carbaldehyde

Base Information

Chemical Name:(Z)-(2S,3S,9R)-3-(tert-Butyl-diphenyl-silanyloxy)-9-((E)-2-methyl-buta-1,3-dienyl)-2,3,4,7,8,9-hexahydro-oxonine-2-carbaldehyde
CAS No.:749924-35-4
Molecular Formula:C₃₀H₃₈O₃Si
Molecular Weight:474.715
Hs Code.:

Synonyms:(Z)-(2S,3S,9R)-3-(tert-Butyl-diphenyl-silanyloxy)-9-((E)-2-methyl-buta-1,3-dienyl)-2,3,4,7,8,9-hexahydro-oxonine-2-carbaldehyde

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Chemical Property of (Z)-(2S,3S,9R)-3-(tert-Butyl-diphenyl-silanyloxy)-9-((E)-2-methyl-buta-1,3-dienyl)-2,3,4,7,8,9-hexahydro-oxonine-2-carbaldehyde

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Technology Process of (Z)-(2S,3S,9R)-3-(tert-Butyl-diphenyl-silanyloxy)-9-((E)-2-methyl-buta-1,3-dienyl)-2,3,4,7,8,9-hexahydro-oxonine-2-carbaldehyde

There total 7 articles about (Z)-(2S,3S,9R)-3-(tert-Butyl-diphenyl-silanyloxy)-9-((E)-2-methyl-buta-1,3-dienyl)-2,3,4,7,8,9-hexahydro-oxonine-2-carbaldehyde 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: 100.0%

: 749924-34-3
[(Z)-(2R,3S,9R)-3-(tert-Butyl-diphenyl-silanyloxy)-9-((E)-2-methyl-buta-1,3-dienyl)-2,3,4,7,8,9-hexahydro-oxonin-2-yl]-methanol

: 749924-35-4
(Z)-(2S,3S,9R)-3-(tert-Butyl-diphenyl-silanyloxy)-9-((E)-2-methyl-buta-1,3-dienyl)-2,3,4,7,8,9-hexahydro-oxonine-2-carbaldehyde

Guidance literature:: With N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; In dichloromethane; for 0.5h;
DOI:10.1055/s-2004-825627

Reference yield:

: 148903-89-3
(Z)-(8S,9R)-8-tert-butyldiphenylsilyloxy-9-tert-butyldiphenylsilyloxymethyl-2,3,4,7,8,9-hexahydro-oxonin-2-one

: 749924-35-4
(Z)-(2S,3S,9R)-3-(tert-Butyl-diphenyl-silanyloxy)-9-((E)-2-methyl-buta-1,3-dienyl)-2,3,4,7,8,9-hexahydro-oxonine-2-carbaldehyde

Guidance literature:: Multi-step reaction with 8 steps

1.1: 83 percent / toluene / 0.5 h / 110 °C

2.1: tetrahydrofuran

2.2: 52 percent / LiAlH₄ / tetrahydrofuran / -78 °C

3.1: m-CPBA / tetrahydrofuran

3.2: NaOAc / tetrahydrofuran

4.1: K₂CO₃ / methanol; CH₂Cl₂ / 16 h

5.1: 62 percent / toluene / 110 °C

6.1: 100 percent / n-BuLi / 2 h / -78 °C

7.1: 89 percent / HF-pyridine / tetrahydrofuran / 3 h

8.1: 100 percent / TPAP; NMO; 4 Angstroem molecular sieves / CH₂Cl₂ / 0.5 h

With n-butyllithium; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; potassium carbonate; pyridine hydrogenfluoride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; dichloromethane; toluene; 1.1: Petasis methylenation / 3.2: Pummerer rearrangement / 5.1: Wittig reaction / 6.1: Wittig methylenation;
DOI:10.1055/s-2004-825627

Reference yield:

: 749924-31-0
(2R,5Z,8S,9R)-8-(tert-butyldiphenylsilanyloxy)-9-(tert-butyldiphenylsilanyloxymethyl)-2,3,4,7,8,9-hexahydrooxonine-2-carbaldehyde

: 749924-35-4
(Z)-(2S,3S,9R)-3-(tert-Butyl-diphenyl-silanyloxy)-9-((E)-2-methyl-buta-1,3-dienyl)-2,3,4,7,8,9-hexahydro-oxonine-2-carbaldehyde

Guidance literature:: Multi-step reaction with 4 steps

1: 62 percent / toluene / 110 °C

2: 100 percent / n-BuLi / 2 h / -78 °C

3: 89 percent / HF-pyridine / tetrahydrofuran / 3 h

4: 100 percent / TPAP; NMO; 4 Angstroem molecular sieves / CH₂Cl₂ / 0.5 h

With n-butyllithium; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; pyridine hydrogenfluoride; In tetrahydrofuran; dichloromethane; toluene; 1: Wittig reaction / 2: Wittig methylenation;
DOI:10.1055/s-2004-825627