dimenthyl (1S,2S)-3-methylcyclopropane-1,2-dicarboxylate

Base Information

Chemical Name:dimenthyl (1S,2S)-3-methylcyclopropane-1,2-dicarboxylate
CAS No.:130799-04-1
Molecular Formula:C₂₆H₄₄O₄
Molecular Weight:420.633
Hs Code.:

Synonyms:dimenthyl (1S,2S)-3-methylcyclopropane-1,2-dicarboxylate

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Chemical Property of dimenthyl (1S,2S)-3-methylcyclopropane-1,2-dicarboxylate

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Technology Process of dimenthyl (1S,2S)-3-methylcyclopropane-1,2-dicarboxylate

There total 1 articles about dimenthyl (1S,2S)-3-methylcyclopropane-1,2-dicarboxylate 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: 45.0%

: 593-96-4
1-bromo-1-chloroethane

: 34212-59-4,96149-05-2
bis(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl butanedioate

: 130799-04-1
dimenthyl (1S,2S)-3-methylcyclopropane-1,2-dicarboxylate

Guidance literature:: With 2,2,6,6-tetramethyl-piperidine; n-butyllithium; In tetrahydrofuran; hexane; 1.) 0 deg C, 65 min; 2.) -78 deg C, 9.5 h;
DOI:10.1016/S0040-4020(01)88025-X

Reference yield: 83.0%

: 130799-04-1
dimenthyl (1S,2S)-3-methylcyclopropane-1,2-dicarboxylate

: 153618-34-9
menthyl (1S,2S,3S)-2-carboxy-3-methylcyclopropane-1-carboxylate

Guidance literature:: With potassium hydroxide; In tetrahydrofuran; ethanol; water; for 84h; Ambient temperature;
DOI:10.1016/S0040-4020(01)88025-X

Reference yield:

: 130799-04-1
dimenthyl (1S,2S)-3-methylcyclopropane-1,2-dicarboxylate

: 58857-02-6
(+)-ambruticin S

Guidance literature:: Multi-step reaction with 14 steps

1: 83 percent / 10percent KOH / tetrahydrofuran; ethanol; H₂O / 84 h / Ambient temperature

2: 100 percent / B₂H₆*THF / Ambient temperature

3: 96 percent / Dess-Martin periodinane / CH₂Cl₂ / Ambient temperature

4: 98 percent / Ph₃P / CH₂Cl₂ / 0.5 h / 0 °C

5: 90 percent / DIBALH / toluene; hexane / 1.) -78 deg C, 10 min; 2.) 0 deg C, 30 min

6: 90 percent / Et₃N, DMAP / dimethylformamide / 72 h / Ambient temperature

7: 92 percent / nBuLi / tetrahydrofuran; hexane / 0.17 h / -78 °C

8: 49 percent / 1.) DIBALH / hexane; tetrahydrofuran / 1.) 50 deg C, 2 h; 2.) -20 deg C, 10 min; RT, 30 min

9: 92 percent / p-toluenesulfonic acid / CH₂Cl₂; methanol / 2 h / Ambient temperature

10: 90 percent / Dess-Martin's periodinane / CH₂Cl₂ / 0.5 h / Ambient temperature

11: 51 percent / nBuLi / diethyl ether; hexane / 1.) 0 deg C, 10 min; 2.) -42 deg C, 135 min

12: 6percent Na(Hg) / methanol; tetrahydrofuran / 3.5 h / -35 °C

13: LiOH / tetrahydrofuran; H₂O / 18 h / Ambient temperature

14: Li/NH₃(l) / ethanol / 0.5 h / -78 °C

With dmap; potassium hydroxide; lithium hydroxide; n-butyllithium; sodium amalgam; B₂H₆-THF; ammonia; lithium; diisobutylaluminium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1016/S0040-4020(01)88025-X