methyl (3S,4R,5R,6S)-3,4,5,6-tetra(acetyloxy)-1-cyclohexene-1-carboxylate

Base Information

Chemical Name:methyl (3S,4R,5R,6S)-3,4,5,6-tetra(acetyloxy)-1-cyclohexene-1-carboxylate
CAS No.:856890-19-2
Molecular Formula:C₁₆H₂₀O₁₀
Molecular Weight:372.329
Hs Code.:

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

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Chemical Property of methyl (3S,4R,5R,6S)-3,4,5,6-tetra(acetyloxy)-1-cyclohexene-1-carboxylate

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

There total 5 articles about methyl (3S,4R,5R,6S)-3,4,5,6-tetra(acetyloxy)-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: 73.0%

: 856890-18-1
(1R,2S,5R,6S)-2,5,6-tri(acetyloxy)-4-iodo-3-cyclohexenyl acetate

: 67-56-1
methanol

: 201230-82-2
carbon monoxide

: 856890-19-2
methyl (3S,4R,5R,6S)-3,4,5,6-tetra(acetyloxy)-1-cyclohexene-1-carboxylate

Guidance literature:: With sodium acetate; palladium diacetate; at 20 ℃; for 6h;
DOI:10.1039/b502009c

Reference yield:

: 138769-92-3
cis-(1S,2S)-1,2-dihydroxy-3-iodocyclohexa-3,5-diene

: 856890-19-2
methyl (3S,4R,5R,6S)-3,4,5,6-tetra(acetyloxy)-1-cyclohexene-1-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

1: 98 percent / p-toluenesulfonic acid / acetone / 4 h / 0 - 20 °C

2: 87 percent / N-methylmorpholine N-oxide; aq. OsO₄ / acetone / 12 h / 20 °C

3: 85 percent / aq. HCl / methanol / 50 °C

4: 87 percent / acetonitrile / 2.25 h / 0 - 20 °C

5: 77 percent / Ac₂O / acetic acid / 1 h / Heating

6: 73 percent / NaOAc*3H₂O / Pd(OAc)2 / 6 h / 20 °C

With hydrogenchloride; osmium(VIII) oxide; sodium acetate; acetic anhydride; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; palladium diacetate; In methanol; acetic acid; acetone; acetonitrile; 5: Woodward-Winstein reaction;
DOI:10.1039/b502009c

Reference yield:

: 165611-18-7
(3aS,4R,5R,7aS)-7-iodo-2,2-dimethyl-3a,4,5,7a-tetrahydro-1,3-benzodioxole-4,5-diol

: 856890-19-2
methyl (3S,4R,5R,6S)-3,4,5,6-tetra(acetyloxy)-1-cyclohexene-1-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1: 85 percent / aq. HCl / methanol / 50 °C

2: 87 percent / acetonitrile / 2.25 h / 0 - 20 °C

3: 77 percent / Ac₂O / acetic acid / 1 h / Heating

4: 73 percent / NaOAc*3H₂O / Pd(OAc)2 / 6 h / 20 °C

With hydrogenchloride; sodium acetate; acetic anhydride; palladium diacetate; In methanol; acetic acid; acetonitrile; 3: Woodward-Winstein reaction;
DOI:10.1039/b502009c