methyl (3R,4R,5S,6S)-6-chloro-3,4,5-trihydroxy-1-cyclohexene-1-carboxylate

Base Information

Chemical Name:methyl (3R,4R,5S,6S)-6-chloro-3,4,5-trihydroxy-1-cyclohexene-1-carboxylate
CAS No.:1054623-08-3
Molecular Formula:C₈H₁₁ClO₅
Molecular Weight:222.625
Hs Code.:

Synonyms:methyl (3R,4R,5S,6S)-6-chloro-3,4,5-trihydroxy-1-cyclohexene-1-carboxylate

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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 (3R,4R,5S,6S)-6-chloro-3,4,5-trihydroxy-1-cyclohexene-1-carboxylate

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Technology Process of methyl (3R,4R,5S,6S)-6-chloro-3,4,5-trihydroxy-1-cyclohexene-1-carboxylate

There total 6 articles about methyl (3R,4R,5S,6S)-6-chloro-3,4,5-trihydroxy-1-cyclohexene-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: 76.0%

: 1054623-14-1
methyl (3aS,4S,5S,7aR)-5-chloro-4-hydroxy-3a,4,5,7a-tetrahydrospiro[benzo[d][1,3]dioxole-2,1'-cyclohexane]-6-carboxylate

: 1054623-08-3
methyl (3R,4R,5S,6S)-6-chloro-3,4,5-trihydroxy-1-cyclohexene-1-carboxylate

Guidance literature:: With trifluoroacetic acid; In methanol; at 20 ℃; for 48h;
DOI:10.1016/j.tetasy.2008.06.008

Reference yield:

: 120200-03-5
methyl (3aS,4R,7aR)-4-hydroxy-3a,4,5,7a-tetrahydrospiro[benzo[d][1,3]dioxole-2,1'-cyclohexane]-6-carboxylate

: 1054623-08-3
methyl (3R,4R,5S,6S)-6-chloro-3,4,5-trihydroxy-1-cyclohexene-1-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1: pyridine; dmap / dichloromethane / 0 - 20 °C

2: cesium acetate / N,N-dimethyl-formamide / 0 - 20 °C

3: potassium peroxymonosulphate; sodium hydrogencarbonate / water / 5 h / -15 - 10 °C

4: hydrogenchloride / diethyl ether / 0 - 20 °C

5: methanol; acetyl chloride

With pyridine; hydrogenchloride; methanol; dmap; potassium peroxymonosulphate; cesium acetate; sodium hydrogencarbonate; acetyl chloride; In diethyl ether; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/acs.jnatprod.9b00415

Reference yield:

: 272123-64-5
methyl (3aR,4R,7aR)-4-(((trifluoromethyl)sulfonyl)oxy)-3a,4,5,7a-tetrahydrospiro[benzo[d][1,3]dioxole-2,1'-cyclohexane]-6-carboxylate

: 1054623-08-3
methyl (3R,4R,5S,6S)-6-chloro-3,4,5-trihydroxy-1-cyclohexene-1-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1: cesium acetate / N,N-dimethyl-formamide / 0 - 20 °C

2: potassium peroxymonosulphate; sodium hydrogencarbonate / water / 5 h / -15 - 10 °C

3: hydrogenchloride / diethyl ether / 0 - 20 °C

4: methanol; acetyl chloride

With hydrogenchloride; methanol; potassium peroxymonosulphate; cesium acetate; sodium hydrogencarbonate; acetyl chloride; In diethyl ether; water; N,N-dimethyl-formamide;
DOI:10.1021/acs.jnatprod.9b00415