(5S,6S)-6-tert-Butoxycarbonylamino-5-(1-methoxycarbonyl-vinyloxy)-cyclohexa-1,3-dienecarboxylic acid methyl ester

Base Information

Chemical Name:(5S,6S)-6-tert-Butoxycarbonylamino-5-(1-methoxycarbonyl-vinyloxy)-cyclohexa-1,3-dienecarboxylic acid methyl ester
CAS No.:89616-69-3
Molecular Formula:C₁₇H₂₃NO₇
Molecular Weight:353.372
Hs Code.:

Synonyms:(5S,6S)-6-tert-Butoxycarbonylamino-5-(1-methoxycarbonyl-vinyloxy)-cyclohexa-1,3-dienecarboxylic acid methyl ester

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Chemical Property of (5S,6S)-6-tert-Butoxycarbonylamino-5-(1-methoxycarbonyl-vinyloxy)-cyclohexa-1,3-dienecarboxylic acid methyl ester

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Technology Process of (5S,6S)-6-tert-Butoxycarbonylamino-5-(1-methoxycarbonyl-vinyloxy)-cyclohexa-1,3-dienecarboxylic acid methyl ester

There total 7 articles about (5S,6S)-6-tert-Butoxycarbonylamino-5-(1-methoxycarbonyl-vinyloxy)-cyclohexa-1,3-dienecarboxylic acid methyl ester 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: 67.0%

: [2-((1S,6S)-6-tert-Butoxycarbonylamino-5-methoxycarbonyl-cyclohexa-2,4-dienyloxy)-2,2-bis-methoxycarbonyl-ethyl]-trimethyl-ammonium; iodide

: 89616-69-3
(5S,6S)-6-tert-Butoxycarbonylamino-5-(1-methoxycarbonyl-vinyloxy)-cyclohexa-1,3-dienecarboxylic acid methyl ester

Guidance literature:: With sodium hydroxide; In methanol; water; at 0 ℃; for 2h;
DOI:10.1021/ja00320a056

Reference yield:

: 58632-95-4
2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile

: 89616-69-3
(5S,6S)-6-tert-Butoxycarbonylamino-5-(1-methoxycarbonyl-vinyloxy)-cyclohexa-1,3-dienecarboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: Et₃N / dioxane; H₂O

2: diethyl ether; methanol / 0 °C

3: 56 percent / Rh₂OAc₄ / benzene / 1 h / 80 °C

4: 93 percent / Et₃N / CH₂Cl₂

5: 97 percent / CH₂Cl₂

6: 67 percent / NaOH / methanol; H₂O / 2 h / 0 °C

With sodium hydroxide; triethylamine; dirhodium tetraacetate; In 1,4-dioxane; methanol; diethyl ether; dichloromethane; water; benzene;
DOI:10.1021/ja00320a056

Reference yield:

: (5S,6S)-6-amino-5-hydroxy-cyclohexa-1,3-diene carboxylic acid

: 89616-69-3
(5S,6S)-6-tert-Butoxycarbonylamino-5-(1-methoxycarbonyl-vinyloxy)-cyclohexa-1,3-dienecarboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: Et₃N / dioxane; H₂O

2: diethyl ether; methanol / 0 °C

3: 56 percent / Rh₂OAc₄ / benzene / 1 h / 80 °C

4: 93 percent / Et₃N / CH₂Cl₂

5: 97 percent / CH₂Cl₂

6: 67 percent / NaOH / methanol; H₂O / 2 h / 0 °C

With sodium hydroxide; triethylamine; dirhodium tetraacetate; In 1,4-dioxane; methanol; diethyl ether; dichloromethane; water; benzene;
DOI:10.1021/ja00320a056