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

Base Information

Chemical Name:Acetic acid (1S,2S,3S,4S,6S)-2,3-diacetoxy-6-tert-butoxycarbonylamino-4-phenylselanyl-cyclohexyl ester
CAS No.:205499-16-7
Molecular Formula:C₂₃H₃₁NO₈Se
Molecular Weight:528.461
Hs Code.:

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

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Chemical Property of Acetic acid (1S,2S,3S,4S,6S)-2,3-diacetoxy-6-tert-butoxycarbonylamino-4-phenylselanyl-cyclohexyl ester

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Technology Process of Acetic acid (1S,2S,3S,4S,6S)-2,3-diacetoxy-6-tert-butoxycarbonylamino-4-phenylselanyl-cyclohexyl ester

There total 13 articles about Acetic acid (1S,2S,3S,4S,6S)-2,3-diacetoxy-6-tert-butoxycarbonylamino-4-phenylselanyl-cyclohexyl 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:

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

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

Guidance literature:: Multi-step reaction with 12 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

With pyridine; dmap; sodium tetrahydroborate; disodium hydrogenphosphate; sodium amalgam; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; methylmagnesium bromide; sodium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; 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

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

Guidance literature:: Multi-step reaction with 11 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

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

Reference yield:

: 205498-95-9
(1S,4R,5R,6R)-5-((S)-1-Methoxycarbonyl-ethoxy)-6-(toluene-4-sulfonyl)-7-aza-bicyclo[2.2.1]hept-2-ene-7-carboxylic acid tert-butyl ester

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

Guidance literature:: Multi-step reaction with 10 steps

1: 92 percent / MeMgBr / toluene; tetrahydrofuran / 0.08 h / Ambient temperature

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

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

4: 88 percent / NaBH₄ / methanol / 2 h / 0 °C

5: 75 percent / Li(NTMS)2 / tetrahydrofuran / 1.) -78 deg C to room temperature, 1 h, 2.) room temperature, 1 h

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

7: 70 percent / Na/Hg, Na₂HPO₄ / tetrahydrofuran; methanol / 1 h / -22 °C

8: 75 percent / MCPBA, NaHCO₃ / CH₂Cl₂ / 16 h / Ambient temperature

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

10: pyridine, DMAP / 16 h

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