methyl (3S,5S)-3,5-dihydroxycyclohex-1-enecarboxylate

Base Information

Chemical Name:methyl (3S,5S)-3,5-dihydroxycyclohex-1-enecarboxylate
CAS No.:120056-36-2
Molecular Formula:C₈H₁₂O₄
Molecular Weight:172.181
Hs Code.:

Synonyms:methyl (3S,5S)-3,5-dihydroxycyclohex-1-enecarboxylate

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of methyl (3S,5S)-3,5-dihydroxycyclohex-1-enecarboxylate

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Technology Process of methyl (3S,5S)-3,5-dihydroxycyclohex-1-enecarboxylate

There total 12 articles about methyl (3S,5S)-3,5-dihydroxycyclohex-1-enecarboxylate 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: 70.0%

: 301153-84-4
methyl (3S,5S)-3,5-di[(p-nitrophenylcarbonyl)oxy]-cyclohex-1-enecarboxylate

: 120056-36-2
methyl (3S,5S)-3,5-dihydroxycyclohex-1-enecarboxylate

Guidance literature:: With sodium methylate; In methanol; at 20 ℃;
DOI:10.1021/jo000443l

Reference yield:

: 76985-84-7
(-)-methyl (1β,2α,6β)-2-hydroxy-7-oxabicyclo<4,1,0>hept-3-ene-4-carboxylate

: 120056-36-2
methyl (3S,5S)-3,5-dihydroxycyclohex-1-enecarboxylate

Guidance literature:: With n-butyllithium; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; Benzeneselenol; Yield given. Multistep reaction; 1.) THF, hexane, -20 deg C, 2 h; 2.) benzene, reflux, 12 h;
DOI:10.1021/ja00191a040

Reference yield:

: 77-95-2
D-(-)-quinic acid

: 120056-36-2
methyl (3S,5S)-3,5-dihydroxycyclohex-1-enecarboxylate

Guidance literature:: Multi-step reaction with 10 steps

1: 100 percent / HCl / 6 h / 60 °C

2: 74 percent / Et₃N / dimethylformamide / 16 h / 20 °C

3: 83 percent / CH₂Cl₂ / 120 h / 20 °C

4: 93 percent / Bu₃SnH; AIBN / toluene / 2 h / 85 °C

5: 80 percent / pyridine; POCl₃ / 10 h / 20 °C

6: 84 percent / TBAF / tetrahydrofuran / 15 h / 0 °C

7: 98 percent / pyridine / 1 h / 20 °C

8: 88 percent / aq. HCl / methanol / 2 h / 20 °C

9: 85 percent / diisopropyl azodicarboxylate; PPh₃ / tetrahydrofuran / 2 h / 20 °C

10: 70 percent / NaOMe / methanol / 20 °C

With pyridine; hydrogenchloride; 2,2'-azobis(isobutyronitrile); di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; sodium methylate; triethylamine; triphenylphosphine; trichlorophosphate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; 1: Methylation / 2: silylation / 3: thioacylation / 4: dethiocarboxylation / 5: Dehydration / 6: Dehydration / 7: Condensation / 8: Hydrolysis / 9: Esterification / 10: ester cleavage;
DOI:10.1021/jo000443l