(3R,5S)-dimethyl-<6-<(tert-butyldiphenylsilyl)oxy>-3-methyl-2-oxo-5-(trimethylsiloxy)hexyl>phosphonate

Base Information

Chemical Name:(3R,5S)-dimethyl-<6-<(tert-butyldiphenylsilyl)oxy>-3-methyl-2-oxo-5-(trimethylsiloxy)hexyl>phosphonate
CAS No.:109000-29-5
Molecular Formula:C₂₈H₄₅O₆PSi₂
Molecular Weight:564.806
Hs Code.:

Synonyms:

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Chemical Property of (3R,5S)-dimethyl-<6-<(tert-butyldiphenylsilyl)oxy>-3-methyl-2-oxo-5-(trimethylsiloxy)hexyl>phosphonate

Chemical Property:

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Technology Process of (3R,5S)-dimethyl-<6-<(tert-butyldiphenylsilyl)oxy>-3-methyl-2-oxo-5-(trimethylsiloxy)hexyl>phosphonate

There total 2 articles about (3R,5S)-dimethyl-<6-<(tert-butyldiphenylsilyl)oxy>-3-methyl-2-oxo-5-(trimethylsiloxy)hexyl>phosphonate 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:

: 102717-29-3
(5S)-5-({[tert-butyl(diphenyl)silyl]oxy}methyl)dihydrofuran-2(3H)-one

: 109000-29-5
(3R,5S)-dimethyl-<6-<(tert-butyldiphenylsilyl)oxy>-3-methyl-2-oxo-5-(trimethylsiloxy)hexyl>phosphonate

Guidance literature:: Multi-step reaction with 2 steps

1: 1.) diisopropylamine, BuLi / 1.) THF, -78 deg C, 30 min 2.) -78 deg C to rt, 20 min

With n-butyllithium; diisopropylamine;
DOI:10.1021/jo00309a022

Reference yield:

: 75-77-4
chloro-trimethyl-silane

: 103233-24-5
(2R,4S)-4-<<(tert-butyldiphenylsilyl)oxy>methyl>-2-methyl-4-butanolide

: 756-79-6
dimethyl methane phosphonate

: 109000-29-5
(3R,5S)-dimethyl-<6-<(tert-butyldiphenylsilyl)oxy>-3-methyl-2-oxo-5-(trimethylsiloxy)hexyl>phosphonate

Guidance literature:: Yield given. Multistep reaction;
DOI:10.1021/jo00309a022

Reference yield:

: 109000-29-5
(3R,5S)-dimethyl-<6-<(tert-butyldiphenylsilyl)oxy>-3-methyl-2-oxo-5-(trimethylsiloxy)hexyl>phosphonate

: 129264-90-0
(1S,2S,4aR,6S,8S,8aS)-1-<2-<2(R)-<1(R)-hydroxy-4(R)-(benzyloxy)cyclopentyl>>ethyl>-2,6-dimethyl-8-<<(S)-2-methyl-1-oxobutyl>oxy>-1,2,4a,5,6,7,8,8a-octahydronaphthalene

Guidance literature:: Multi-step reaction with 27 steps

2: 62 percent / L-Selectride / tetrahydrofuran / 0.42 h / -78 °C

3: 85 percent / diisopropylethylamine, dimethylaminopyridine / CH₂Cl₂ / 3 h / Ambient temperature

4: 98 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature

5: 75 percent / pyridine / CH₂Cl₂ / -5 °C

6: 87 percent / sodium methoxide / CH₂Cl₂; methanol / 0.67 h / 0 °C

8: 65 percent / 2,6-di-tert-butyl-4-methylphenol / o-xylene / 144 h / Heating

9: 95 percent / 6 M HCl / tetrahydrofuran / 19 h / 40 °C

11: 68 percent / n-Bu₃SnH, AIBN / toluene / 0.58 h / Heating

12: 94 percent / LAH / tetrahydrofuran / 0.5 h / 0 °C

13: 91 percent / pyridine / Ambient temperature

14: 85 percent / triethylamine / CH₂Cl₂ / 0.5 h / Ambient temperature

15: 90 percent / LAH / tetrahydrofuran / 0.67 h / 0 °C

16: 1.) oxalyl chloride, dimethylsulfoxide 2.) triethylamine / 1.) CH₂Cl₂, -10 deg C, 20 min 2.) -10 deg C, 5 min

17: 53 percent / K₂CO₃ / methanol / 19 h / 100 °C

18: 73 percent / sodium methoxide / methanol / 2 h / Ambient temperature

19: 85 percent / methanesulfonyl chloride, triethylamine / CH₂Cl₂ / 1 h / 0 °C

20: 90 percent / NaBH₄ / propan-2-ol; CHCl₃ / 0.67 h / Ambient temperature

21: 93 percent / aq.HF / acetonitrile / 24 h / Ambient temperature

22: 70 percent / DMAP / 0.33 h / 40 °C

23: 70 percent / Amberlyst A-21 / diethyl ether / 2 h / Ambient temperature

24: 55 percent / n-Bu₃SnH, AIBN / toluene / 0.5 h / Heating

25: 0.034 g / sodium borohydride / propan-2-ol; tetrahydrofuran / -78 deg C to rt, overnight

26: 80 percent / n-tetrabutylammonium iodide, NaH / tetrahydrofuran / 18 h / Ambient temperature

27: 85 percent / 48percent aq. HF / acetonitrile / 1.5 h / Ambient temperature

With pyridine; hydrogenchloride; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; oxalyl dichloride; Amberlyst A-21; 2,2'-azobis(isobutyronitrile); 2,6-di-tert-butyl-4-methyl-phenol; hydrogen fluoride; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; sodium methylate; tetra-(n-butyl)ammonium iodide; L-Selectride; sodium hydride; potassium carbonate; dimethyl sulfoxide; methanesulfonyl chloride; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; chloroform; o-xylene; isopropyl alcohol; toluene; acetonitrile;
DOI:10.1021/jo00309a022