Kishi's aldehyde

Base Information

Chemical Name:Kishi's aldehyde
CAS No.:155433-69-5
Molecular Formula:C₆₂H₈₀O₁₃
Molecular Weight:1033.31
Hs Code.:

Synonyms:Kishi's aldehyde

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Chemical Property of Kishi's aldehyde

Chemical Property:

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Technology Process of Kishi's aldehyde

There total 81 articles about Kishi's aldehyde 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: 89.0%

: 137531-93-2
(3R,4R)-4-Benzyloxymethoxy-3-(4-methoxy-benzyloxy)-pentanoic acid (1S,2S,3R,4S,7S)-7-(3-benzyloxymethoxy-phenyl)-7-methoxy-3-(4-methoxy-benzyloxy)-2,4-dimethyl-1-[2-((R)-1,1,3-trimethyl-4-oxo-butyl)-[1,3]dithian-2-ylmethyl]-heptyl ester

: 155433-69-5
Kishi's aldehyde

Guidance literature:: With N-chloro-succinimide; silver nitrate; In acetone; for 0.5h; Ambient temperature;
DOI:10.1016/S0040-4020(01)81547-7

Reference yield:

: 3587-60-8
Benzyloxymethyl chloride

: 155433-69-5
Kishi's aldehyde

Guidance literature:: Multi-step reaction with 21 steps

2: 92 percent / diisobutyl aluminum hydride / CH₂Cl₂; hexane / 1 h / -78 °C

3: 90 percent / (-)-diisopropyl tartrate, titanium tetraisopropoxide, t-butyl hydroperoxide, MS 4 Angstroem / CH₂Cl₂; toluene / 11 h / -20 °C

4: 91 percent / Red-al / toluene; tetrahydrofuran / 10.2 h / 0 °C

5: 93 percent / triethylamine, 4-DMAP / CH₂Cl₂ / 4 h / Ambient temperature

6: sodium hydride / tetrahydrofuran; dimethylformamide / 5 h / Ambient temperature

7: sodium bromide / dimethylformamide / 48 h / Ambient temperature

8: Mg / tetrahydrofuran / 1 h / Irradiation

9: CuI / tetrahydrofuran

10: 93 percent / 4-dimethylaminopyridine / tetrahydrofuran / 12 h / Ambient temperature

11: 62 percent / lithium aluminum hydride / tetrahydrofuran / 14 h / Ambient temperature

12: 91 percent / 4-dimethylaminopyridine / CH₂Cl₂ / 12 h / Ambient temperature

13: 86 percent / PPTS / methanol / 36 h / Ambient temperature

14: 97 percent / 4-dimethylaminopyridine / CH₂Cl₂ / 12 h / Ambient temperature

15: 31 percent / aq. KOH; methanol / 24 h / Ambient temperature

16: 87 percent / NaH / tetrahydrofuran; dimethylformamide / 24 h / Ambient temperature

17: 1.) n-butyllithium, tetramethylethylenediamine / 1.) THF, hexane, -20 deg C, 11 h; 2.) -20 deg C, 10 h

18: 85 percent / 4-dimethylaminopyridine / toluene / 1 h / 50 °C

19: 90 percent / PPTS / methanol / 40 h / Ambient temperature

20: 85 percent / potassium acetate, lead tetraacetate / acetonitrile / 0.5 h / -20 °C

21: 89 percent / AgNO₃, N-chlorosuccinimide / acetone / 0.5 h / Ambient temperature

With lead(IV) acetate; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; N-chloro-succinimide; lithium aluminium tetrahydride; n-butyllithium; (-)-diisopropyl tartrate; N,N,N,N,-tetramethylethylenediamine; MS 4 Angstroem; potassium acetate; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; silver nitrate; magnesium; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; sodium bromide; copper(l) iodide; In tetrahydrofuran; methanol; potassium hydroxide; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; acetonitrile;
DOI:10.1016/S0040-4020(01)81547-7

Reference yield:

: (2R,3S,4R,5S,8S)-8-(3-Benzyloxymethoxy-phenyl)-8-methoxy-4-(4-methoxy-benzyloxy)-3,5-dimethyl-octane-1,2-diol

: 155433-69-5
Kishi's aldehyde

Guidance literature:: Multi-step reaction with 6 steps

1: 78 percent / p-toluenesulfonyl chloride, potassium t-butoxide / tetrahydrofuran / 0.5 h / Ambient temperature

2: 1.) n-butyllithium, tetramethylethylenediamine / 1.) THF, hexane, -20 deg C, 11 h; 2.) -20 deg C, 10 h

3: 85 percent / 4-dimethylaminopyridine / toluene / 1 h / 50 °C

4: 90 percent / PPTS / methanol / 40 h / Ambient temperature

5: 85 percent / potassium acetate, lead tetraacetate / acetonitrile / 0.5 h / -20 °C

6: 89 percent / AgNO₃, N-chlorosuccinimide / acetone / 0.5 h / Ambient temperature

With lead(IV) acetate; dmap; N-chloro-succinimide; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; potassium tert-butylate; potassium acetate; pyridinium p-toluenesulfonate; silver nitrate; p-toluenesulfonyl chloride; In tetrahydrofuran; methanol; acetone; toluene; acetonitrile;
DOI:10.1016/S0040-4020(01)81547-7