2-<(2S,4R,6R,8R,9S)-4-<(tert-butyldiphenylsilyl)oxy>-8,9-dimethyl-1,7-dioxaspiro<5.5>undecyl>ethanal

Base Information

• Chemical Name: 2-<(2S,4R,6R,8R,9S)-4-<(tert-butyldiphenylsilyl)oxy>-8,9-dimethyl-1,7-dioxaspiro<5.5>undecyl>ethanal
• CAS No.: 104705-91-1
• Molecular Formula: C₂₉H₄₀O₄Si
• Molecular Weight: 480.72
• Mol file: 104705-91-1.mol

Synonyms:2-<(2S,4R,6R,8R,9S)-4-<(tert-butyldiphenylsilyl)oxy>-8,9-dimethyl-1,7-dioxaspiro<5.5>undecyl>ethanal

Chemical Property of 2-<(2S,4R,6R,8R,9S)-4-<(tert-butyldiphenylsilyl)oxy>-8,9-dimethyl-1,7-dioxaspiro<5.5>undecyl>ethanal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-<(2S,4R,6R,8R,9S)-4-<(tert-butyldiphenylsilyl)oxy>-8,9-dimethyl-1,7-dioxaspiro<5.5>undecyl>ethanal

There total 48 articles about 2-<(2S,4R,6R,8R,9S)-4-<(tert-butyldiphenylsilyl)oxy>-8,9-dimethyl-1,7-dioxaspiro<5.5>undecyl>ethanal 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: 92.0%

(2R,4R,6R,8R,9S)-4-<(tert-butyldiphenylsilyl)oxy>-2-(2-hydroxyethyl)-8,9-dimethyl-1,7-dioxaspiro<5.5>undecane (104996-39-6) → 2-<(2S,4R,6R,8R,9S)-4-<(tert-butyldiphenylsilyl)oxy>-8,9-dimethyl-1,7-dioxaspiro<5.5>undecyl>ethanal (104705-91-1)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 3h;

DOI:10.1021/ol061439k

Reference yield:

(6S,8R,9S)-methyl 8,9-dimethyl-4-oxo-1,7-dioxaspiro<5,5>undec-2-ene-2-carboxylate (104705-88-6) → 2-<(2S,4R,6R,8R,9S)-4-<(tert-butyldiphenylsilyl)oxy>-8,9-dimethyl-1,7-dioxaspiro<5.5>undecyl>ethanal (104705-91-1)

Guidance literature:

Multi-step reaction with 5 steps

1: H₂ / Rh-Al₂O₃ / ethanol

2: 1.) imidazole, 2.) LiN(i-Pr)2 then HOAc / 1.) DMF, 2.) THF, -78 deg C

3: 1.) i-Bu₂AlH / 1.) toluene, -78 deg C, 2.) THF, 0 deg C

4: 1.) B₂H₆, 2.) NaOH, H₂O₂ / 1.) Et₂O

5: pyridinium chlorochromate / CH₂Cl₂

With 1H-imidazole; sodium hydroxide; hydrogen; dihydrogen peroxide; diisobutylaluminium hydride; acetic acid; pyridinium chlorochromate; diborane; lithium diisopropyl amide; rhodium on alumina; In ethanol; dichloromethane;

DOI:10.1039/c39860000479

Reference yield:

6-(4-methoxyphenoxy)hex-1-yne (912457-49-9) → 2-<(2S,4R,6R,8R,9S)-4-<(tert-butyldiphenylsilyl)oxy>-8,9-dimethyl-1,7-dioxaspiro<5.5>undecyl>ethanal (104705-91-1)

Guidance literature:

Multi-step reaction with 15 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

1.2: 95 percent / tetrahydrofuran; hexane / -78 - 0 °C

2.1: 97 percent / Ph₃P; phenol / benzene / 12 h / 20 °C

3.1: K₃[Fe(CN)6]; OsO₄; K₂CO₃ / MeSO₂NH₂; (DHQD)2-PHAL / 2-methyl-propan-2-ol; H₂O / 0 °C

3.2: pyridine; DMAP / CH₂Cl₂ / 2 h / -78 - 0 °C

4.1: 93 percent / HCO₂H; PPh₃; triethylamine / Pd₂(dba)3*HCl / tetrahydrofuran / 20 °C

5.1: 61 percent / t-BuOK / tetrahydrofuran / 0 °C

6.1: 89 percent / iPrMgCl / tetrahydrofuran / 1 h / -20 °C

7.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

7.2: 84 percent / tetrahydrofuran; hexane / 1 h / -78 °C

8.1: Cs₂CO₃ / propan-2-ol / 0.08 h / 0 °C

8.2: 82 percent / propan-2-ol / 3 h / 20 °C

9.1: 58 percent / K₃[Fe(CN)6]; OsO₄; K₂CO₃ / MeSO₂NH₂; (DHQD)2-PHAL / 2-methyl-propan-2-ol; H₂O / 5 h / 0 °C

10.1: 98 percent / pyridine; DMAP / CH₂Cl₂ / 2 h / -78 - 0 °C

11.1: 83 percent / HCO₂H; triethylamine; PPh₃ / Pd₂(dba)3*CHCl₃ / tetrahydrofuran / 20 °C

12.1: 92 percent / H₂ / Pd/C / methanol / 12 h / 760 Torr

13.1: 94 percent / imidazole / dimethylformamide / 12 h / 50 °C

14.1: 96 percent / ceric ammonium nitrate / acetonitrile; H₂O / 0.17 h / 0 °C

15.1: 92 percent / Dess-Martin periodinane / CH₂Cl₂ / 3 h / 20 °C

With pyridine; 1H-imidazole; dmap; osmium(VIII) oxide; n-butyllithium; formic acid; ammonium cerium(IV) nitrate; potassium tert-butylate; hydrogen; isopropylmagnesium chloride; potassium carbonate; caesium carbonate; Dess-Martin periodane; triethylamine; triphenylphosphine; potassium hexacyanoferrate(III); phenol; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; palladium on activated charcoal; methanesulfonamide; Pd₂(dba)3*HCl; 1,4-bis(9-O-dihydroquinidine)phthalazine; In tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; isopropyl alcohol; acetonitrile; tert-butyl alcohol; benzene; 7.2: Horner-Wadsworth-Emmons reaction / 8.2: Horner-Wadsworth-Emmons reaction;

DOI:10.1021/ol061439k

upstream raw materials:

(2R,3S,6S,8R,10R)-(+)-10-diphenyl-t-butylsilyloxy-8-cyanomethyl-2,3-dimethyl-1,7-dioxaspiro<5.5>undecane

2(S)-(2-hydroxyethyl)-4(S)-<(tert-butyldiphenylsilyl)oxy>-8(R),9(S)-dimethyl-1,7-dioxaspiro<5.5>undecane

(+)-(5S,6R)-tetrahydro-5,6-dimethyl-2H-pyran-2-one

8(R),9(S)-dimethyl-1,7-dioxaspiro<5.5>undec-2-en-4-one

Downstream raw materials:

(2'R,3'S,6'S,8'S,10'R)-(E)-(+)-ethyl 4-(10'diphenyl-t-butylsiloxy-2',3'-dimethyl-1',7'-dioxaspiro<5.5>undecane-8'-yl)-2-methylbut-2-enoate

(2'R,3'S,6'S,8'R,10'R)-(E)-(+)-4-(10'diphenyl-t-butylsiloxy-2',3'-dimethyl-1',7'-dioxaspiro<5.5>undecan-8'-yl)-2-methylbut-2-enol

(2R,2'R,3'S,6'S,8'R,10'R)-(+)-6-(10'-diphenyl-t-butylsiloxy-2',3'-dimethyl-1',7'-dioxaspiro<5.5>undecan-8'-yl)-2,4-dimethylhex-4-enol

[(2R,4S,6R,8R,9S)-2-((E)-4-Bromo-3-methyl-but-2-enyl)-8,9-dimethyl-1,7-dioxa-spiro[5.5]undec-4-yloxy]-tert-butyl-diphenyl-silane