Acetic acid (1S,2S,5R,6R)-5,6-diacetoxy-2-tert-butoxycarbonylamino-cyclohex-3-enyl ester

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Chemical Name:Acetic acid (1S,2S,5R,6R)-5,6-diacetoxy-2-tert-butoxycarbonylamino-cyclohex-3-enyl ester
CAS No.:205499-18-9
Molecular Formula:C₁₇H₂₅NO₈
Molecular Weight:371.387
Hs Code.:

Synonyms:Acetic acid (1S,2S,5R,6R)-5,6-diacetoxy-2-tert-butoxycarbonylamino-cyclohex-3-enyl ester

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Chemical Property of Acetic acid (1S,2S,5R,6R)-5,6-diacetoxy-2-tert-butoxycarbonylamino-cyclohex-3-enyl ester

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Technology Process of Acetic acid (1S,2S,5R,6R)-5,6-diacetoxy-2-tert-butoxycarbonylamino-cyclohex-3-enyl ester

There total 14 articles about Acetic acid (1S,2S,5R,6R)-5,6-diacetoxy-2-tert-butoxycarbonylamino-cyclohex-3-enyl 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: 91.0%

: 205499-16-7
Acetic acid (1S,2S,3S,4S,6S)-2,3-diacetoxy-6-tert-butoxycarbonylamino-4-phenylselanyl-cyclohexyl ester

: 205499-18-9
Acetic acid (1S,2S,5R,6R)-5,6-diacetoxy-2-tert-butoxycarbonylamino-cyclohex-3-enyl ester

Guidance literature:: With dihydrogen peroxide; N-ethyl-N,N-diisopropylamine; 1.) 0 deg C, CH₂Cl₂, 15 min, 2.) THF, 50 deg C, 1.5 h;
DOI:10.1021/jo971907r

Reference yield:

: 5176-27-2
N-tert-butyloxycarbonyl-pyrrole

: 205499-18-9
Acetic acid (1S,2S,5R,6R)-5,6-diacetoxy-2-tert-butoxycarbonylamino-cyclohex-3-enyl ester

Guidance literature:: Multi-step reaction with 13 steps

1: 84 percent / 48 h / 80 - 85 °C

2: 47 percent / NaH / tetrahydrofuran / 2 h

3: 92 percent / MeMgBr / toluene; tetrahydrofuran / 0.08 h / Ambient temperature

4: 84 percent / NMO, OsO₄, NaHCO₃ / tetrahydrofuran; 2-methyl-propan-2-ol; H₂O / 6 h / Ambient temperature

5: 96 percent / p-TsOH*H₂O / acetone / 3 h / Ambient temperature

6: 88 percent / NaBH₄ / methanol / 2 h / 0 °C

7: 75 percent / Li(NTMS)2 / tetrahydrofuran / 1.) -78 deg C to room temperature, 1 h, 2.) room temperature, 1 h

8: 92 percent / p-TsOH*H₂O / methanol / 6 h / Ambient temperature

9: 70 percent / Na/Hg, Na₂HPO₄ / tetrahydrofuran; methanol / 1 h / -22 °C

10: 75 percent / MCPBA, NaHCO₃ / CH₂Cl₂ / 16 h / Ambient temperature

11: n-BuLi / tetrahydrofuran / 16 h / Ambient temperature

12: pyridine, DMAP / 16 h

13: 91 percent / aq. H₂O₂, iPr₂NEt / 1.) 0 deg C, CH₂Cl₂, 15 min, 2.) THF, 50 deg C, 1.5 h

With pyridine; dmap; sodium tetrahydroborate; disodium hydrogenphosphate; sodium amalgam; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; methylmagnesium bromide; dihydrogen peroxide; sodium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; water; acetone; toluene; tert-butyl alcohol;
DOI:10.1021/jo971907r

Reference yield:

: (1S,4R)-2-(Toluene-4-sulfonyl)-7-aza-bicyclo[2.2.1]hepta-2,5-diene-7-carboxylic acid tert-butyl ester

: 205499-18-9
Acetic acid (1S,2S,5R,6R)-5,6-diacetoxy-2-tert-butoxycarbonylamino-cyclohex-3-enyl ester

Guidance literature:: Multi-step reaction with 12 steps

1: 47 percent / NaH / tetrahydrofuran / 2 h

2: 92 percent / MeMgBr / toluene; tetrahydrofuran / 0.08 h / Ambient temperature

3: 84 percent / NMO, OsO₄, NaHCO₃ / tetrahydrofuran; 2-methyl-propan-2-ol; H₂O / 6 h / Ambient temperature

4: 96 percent / p-TsOH*H₂O / acetone / 3 h / Ambient temperature

5: 88 percent / NaBH₄ / methanol / 2 h / 0 °C

6: 75 percent / Li(NTMS)2 / tetrahydrofuran / 1.) -78 deg C to room temperature, 1 h, 2.) room temperature, 1 h

7: 92 percent / p-TsOH*H₂O / methanol / 6 h / Ambient temperature

8: 70 percent / Na/Hg, Na₂HPO₄ / tetrahydrofuran; methanol / 1 h / -22 °C

9: 75 percent / MCPBA, NaHCO₃ / CH₂Cl₂ / 16 h / Ambient temperature

10: n-BuLi / tetrahydrofuran / 16 h / Ambient temperature

11: pyridine, DMAP / 16 h

12: 91 percent / aq. H₂O₂, iPr₂NEt / 1.) 0 deg C, CH₂Cl₂, 15 min, 2.) THF, 50 deg C, 1.5 h

With pyridine; dmap; sodium tetrahydroborate; disodium hydrogenphosphate; sodium amalgam; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; methylmagnesium bromide; dihydrogen peroxide; sodium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; water; acetone; toluene; tert-butyl alcohol;
DOI:10.1021/jo971907r