methyl 3α,4α-hydroxy-5β-<2-methoxycarbonylprop-1-en-3-yl>-cyclohex-1-ene-1-carboxylate

Base Information

Chemical Name:methyl 3α,4α-hydroxy-5β-<2-methoxycarbonylprop-1-en-3-yl>-cyclohex-1-ene-1-carboxylate
CAS No.:142945-29-7
Molecular Formula:C₁₃H₁₈O₆
Molecular Weight:270.282
Hs Code.:

Synonyms:methyl 3α,4α-hydroxy-5β-<2-methoxycarbonylprop-1-en-3-yl>-cyclohex-1-ene-1-carboxylate

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Chemical Property of methyl 3α,4α-hydroxy-5β-<2-methoxycarbonylprop-1-en-3-yl>-cyclohex-1-ene-1-carboxylate

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Technology Process of methyl 3α,4α-hydroxy-5β-<2-methoxycarbonylprop-1-en-3-yl>-cyclohex-1-ene-1-carboxylate

There total 7 articles about methyl 3α,4α-hydroxy-5β-<2-methoxycarbonylprop-1-en-3-yl>-cyclohex-1-ene-1-carboxylate 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: 47.0%

: 142945-27-5,145433-85-8
methyl 3α,4α-isopropylidenedioxy-5β-<2-methoxycarbonylprop-1-en-3-yl>-cyclohex-1-ene-1-carboxylate

: 142945-28-6
(4aR,8R,8aS)-8-Hydroxy-3-methylene-2-oxo-3,4,4a,5,8,8a-hexahydro-2H-chromene-6-carboxylic acid methyl ester

: 142945-29-7
methyl 3α,4α-hydroxy-5β-<2-methoxycarbonylprop-1-en-3-yl>-cyclohex-1-ene-1-carboxylate

Guidance literature:: With acetic acid; In tetrahydrofuran; at 50 - 60 ℃; for 36h;
DOI:10.1016/S0040-4020(01)85625-8

Reference yield:

: 134039-38-6
methyl 3α,4α-isopropylidenedioxy-5β-(iodomethyl)cyclohex-1-ene-1-carboxylate

: 142945-29-7
methyl 3α,4α-hydroxy-5β-<2-methoxycarbonylprop-1-en-3-yl>-cyclohex-1-ene-1-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) LDA, DMPU / 1.) THF, hexane, -78 deg C, 1 h, 2a.) THF, -78 deg C, 5 h, 2b.) 0 deg C, 8 h

2: 86 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene / tetrahydrofuran / 4 h / 20 °C

3: 47 percent / 50 percent aq. AcOH / tetrahydrofuran / 36 h / 50 - 60 °C

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium diisopropyl amide; In tetrahydrofuran;
DOI:10.1016/S0040-4020(01)85625-8

Reference yield:

: 142954-45-8
methyl 3α,4α-isopropylidenedioxy-5β-<2-methoxycarbonyl-1-nitroprop-3-yl>-cyclohex-1-ene-1-carboxylate

: 142945-29-7
methyl 3α,4α-hydroxy-5β-<2-methoxycarbonylprop-1-en-3-yl>-cyclohex-1-ene-1-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: 86 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene / tetrahydrofuran / 4 h / 20 °C

2: 47 percent / 50 percent aq. AcOH / tetrahydrofuran / 36 h / 50 - 60 °C

With acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran;
DOI:10.1016/S0040-4020(01)85625-8