(3R,11R)-29-benzyloxy-3,11-dimethylnonacos-14-yn-2-one

Base Information

Chemical Name:(3R,11R)-29-benzyloxy-3,11-dimethylnonacos-14-yn-2-one
CAS No.:79016-00-5
Molecular Formula:C₃₈H₆₄O₂
Molecular Weight:552.925
Hs Code.:

Synonyms:

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Chemical Property of (3R,11R)-29-benzyloxy-3,11-dimethylnonacos-14-yn-2-one

Chemical Property:

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Technology Process of (3R,11R)-29-benzyloxy-3,11-dimethylnonacos-14-yn-2-one

There total 23 articles about (3R,11R)-29-benzyloxy-3,11-dimethylnonacos-14-yn-2-one 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:

: 79015-98-8
(3R,11R)-29-benzyloxy-3,11-dimethylnonacos-14-yn-2-ol

: 79016-00-5
(3R,11R)-29-benzyloxy-3,11-dimethylnonacos-14-yn-2-one

Guidance literature:: With chromium(VI) oxide; In acetone;
DOI:10.1016/S0040-4020(01)92448-2

Reference yield:

: 1117-61-9
(3R)-citronellol

: 79016-00-5
(3R,11R)-29-benzyloxy-3,11-dimethylnonacos-14-yn-2-one

Guidance literature:: Multi-step reaction with 15 steps

1: pyridine / 2 h / 0 - 5 °C

2: 85 percent / sodium iodide / acetone / 1.) reflux, 4 h; 2.) room temp., 14 h

3: 62.3 percent / NaNH₂ / liquid ammonia; dimethylsulfoxide / 4 h / Ambient temperature

4: 22.8 g / n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / 1 h / -10 - 25 °C

5: 22.7 g / m-chloroperbenzoic acid / CHCl₃ / 2 h / Ambient temperature

6: 20.2 g / HIO₄*2H₂O / diethyl ether; tetrahydrofuran / 1.5 h / Ambient temperature

7: 9.65 g / LAH / diethyl ether / 4 h / Ambient temperature

8: 10.4 g / pyridine / 1.5 h / 0 - 5 °C

9: 7.74 g / NaCN / dimethylsulfoxide / 16 h / 60 - 65 °C

10: 6.4 percent / NaOH / ethanol; H₂O / 17 h / Heating

11: 4.51 g / LAH / diethyl ether / 5 h / Ambient temperature

12: 2.96 g / pyridine / 2 h / 0 - 5 °C

13: 1.) Mg; 2.) 0.1 M Li₂CuCl₄ / 1.) ether; 2.) THF, -60 deg C,

14: 1.) Hg(OAc)2, 2.) NaBH₄, NaOH / 1.) 3h, room temp., THF-H₂O; 2.) H₂O, 30 min, room temp

15: 640 mg / Jones CrO₃ / acetone

With chromium(VI) oxide; sodium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; n-butyllithium; dilithium tetrachlorocuprate; sodium cyanide; mercury(II) diacetate; sodium amide; magnesium; periodic acid; 3-chloro-benzenecarboperoxoic acid; sodium iodide; In tetrahydrofuran; pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; ethanol; chloroform; ammonia; water; dimethyl sulfoxide; acetone;
DOI:10.1016/S0040-4020(01)92448-2

Reference yield:

: 18951-85-4,57030-77-0
(R)-citronellic acid

: 79016-00-5
(3R,11R)-29-benzyloxy-3,11-dimethylnonacos-14-yn-2-one

Guidance literature:: Multi-step reaction with 16 steps

1: 92 percent / LAH / diethyl ether / 3 h / Ambient temperature

2: pyridine / 2 h / 0 - 5 °C

3: 85 percent / sodium iodide / acetone / 1.) reflux, 4 h; 2.) room temp., 14 h

4: 62.3 percent / NaNH₂ / liquid ammonia; dimethylsulfoxide / 4 h / Ambient temperature

5: 22.8 g / n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / 1 h / -10 - 25 °C

6: 22.7 g / m-chloroperbenzoic acid / CHCl₃ / 2 h / Ambient temperature

7: 20.2 g / HIO₄*2H₂O / diethyl ether; tetrahydrofuran / 1.5 h / Ambient temperature

8: 9.65 g / LAH / diethyl ether / 4 h / Ambient temperature

9: 10.4 g / pyridine / 1.5 h / 0 - 5 °C

10: 7.74 g / NaCN / dimethylsulfoxide / 16 h / 60 - 65 °C

11: 6.4 percent / NaOH / ethanol; H₂O / 17 h / Heating

12: 4.51 g / LAH / diethyl ether / 5 h / Ambient temperature

13: 2.96 g / pyridine / 2 h / 0 - 5 °C

14: 1.) Mg; 2.) 0.1 M Li₂CuCl₄ / 1.) ether; 2.) THF, -60 deg C,

15: 1.) Hg(OAc)2, 2.) NaBH₄, NaOH / 1.) 3h, room temp., THF-H₂O; 2.) H₂O, 30 min, room temp

16: 640 mg / Jones CrO₃ / acetone

With chromium(VI) oxide; sodium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; n-butyllithium; dilithium tetrachlorocuprate; sodium cyanide; mercury(II) diacetate; sodium amide; magnesium; periodic acid; 3-chloro-benzenecarboperoxoic acid; sodium iodide; In tetrahydrofuran; pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; ethanol; chloroform; ammonia; water; dimethyl sulfoxide; acetone;
DOI:10.1016/S0040-4020(01)92448-2