((3aR,4R,6S,7S,7aS)-7-Hydroxy-2,2-dimethyl-6-phenylselanyl-hexahydro-benzo[1,3]dioxol-4-yl)-carbamic acid tert-butyl ester

Base Information

• Chemical Name: ((3aR,4R,6S,7S,7aS)-7-Hydroxy-2,2-dimethyl-6-phenylselanyl-hexahydro-benzo[1,3]dioxol-4-yl)-carbamic acid tert-butyl ester
• CAS No.: 205499-10-1
• Molecular Formula: C₂₀H₂₉NO₅Se
• Molecular Weight: 442.414
• Mol file: 205499-10-1.mol

Synonyms:((3aR,4R,6S,7S,7aS)-7-Hydroxy-2,2-dimethyl-6-phenylselanyl-hexahydro-benzo[1,3]dioxol-4-yl)-carbamic acid tert-butyl ester

Chemical Property of ((3aR,4R,6S,7S,7aS)-7-Hydroxy-2,2-dimethyl-6-phenylselanyl-hexahydro-benzo[1,3]dioxol-4-yl)-carbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((3aR,4R,6S,7S,7aS)-7-Hydroxy-2,2-dimethyl-6-phenylselanyl-hexahydro-benzo[1,3]dioxol-4-yl)-carbamic acid tert-butyl ester

There total 14 articles about ((3aR,4R,6S,7S,7aS)-7-Hydroxy-2,2-dimethyl-6-phenylselanyl-hexahydro-benzo[1,3]dioxol-4-yl)-carbamic acid tert-butyl 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: 85.0%

diphenyl diselenide (1666-13-3) + ((1aR,3R,3aR,6aR,6bR)-5,5-Dimethyl-hexahydro-1,4,6-trioxa-cyclopropa[e]inden-3-yl)-carbamic acid tert-butyl ester (205813-85-0) → ((3aR,4R,6S,7S,7aS)-7-Hydroxy-2,2-dimethyl-6-phenylselanyl-hexahydro-benzo[1,3]dioxol-4-yl)-carbamic acid tert-butyl ester (205499-10-1)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; for 16h; Ambient temperature;

DOI:10.1021/jo971907r

Reference yield:

N-tert-butyloxycarbonyl-pyrrole (5176-27-2) → ((3aR,4R,6S,7S,7aS)-7-Hydroxy-2,2-dimethyl-6-phenylselanyl-hexahydro-benzo[1,3]dioxol-4-yl)-carbamic acid tert-butyl ester (205499-10-1)

Guidance literature:

Multi-step reaction with 13 steps

1: 84 percent / 48 h / 80 - 85 °C

2: 48 percent / NaH / tetrahydrofuran / 2 h

3: 95 percent / NaBH₄ / tetrahydrofuran; methanol / 2 h / 70 °C

4: 95 percent / MeMgBr / toluene; tetrahydrofuran / 0.08 h / Ambient temperature

5: 89 percent / NMO, OsO₄, NaHCO₃ / tetrahydrofuran; 2-methyl-propan-2-ol; H₂O / 2.5 h / Ambient temperature

6: 97 percent / p-TsOH*H₂O / acetone / 0.5 h / Ambient temperature

7: 85 percent / NaBH₄ / methanol / 2 h / 0 °C

8: 80 percent / Li(NTMS)2 / tetrahydrofuran / 1.) -78 deg C to room temperature, 1 h, 2.) room temperature, 1 h

9: 95 percent / p-TsOH*H₂O / methanol / 6 h / Ambient temperature

10: 84 percent / Na/Hg, Na₂HPO₄ / tetrahydrofuran; methanol / 1 h / -22 °C

11: 94 percent / p-TsOH*H₂O / acetone / 0.5 h / Ambient temperature

12: 97 percent / MCPBA, NaHCO₃ / CH₂Cl₂ / 16 h / Ambient temperature

13: 85 percent / n-BuLi / tetrahydrofuran / 16 h / Ambient temperature

With 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 → ((3aR,4R,6S,7S,7aS)-7-Hydroxy-2,2-dimethyl-6-phenylselanyl-hexahydro-benzo[1,3]dioxol-4-yl)-carbamic acid tert-butyl ester (205499-10-1)

Guidance literature:

Multi-step reaction with 12 steps

1: 48 percent / NaH / tetrahydrofuran / 2 h

2: 95 percent / NaBH₄ / tetrahydrofuran; methanol / 2 h / 70 °C

3: 95 percent / MeMgBr / toluene; tetrahydrofuran / 0.08 h / Ambient temperature

4: 89 percent / NMO, OsO₄, NaHCO₃ / tetrahydrofuran; 2-methyl-propan-2-ol; H₂O / 2.5 h / Ambient temperature

5: 97 percent / p-TsOH*H₂O / acetone / 0.5 h / Ambient temperature

6: 85 percent / NaBH₄ / methanol / 2 h / 0 °C

7: 80 percent / Li(NTMS)2 / tetrahydrofuran / 1.) -78 deg C to room temperature, 1 h, 2.) room temperature, 1 h

8: 95 percent / p-TsOH*H₂O / methanol / 6 h / Ambient temperature

9: 84 percent / Na/Hg, Na₂HPO₄ / tetrahydrofuran; methanol / 1 h / -22 °C

10: 94 percent / p-TsOH*H₂O / acetone / 0.5 h / Ambient temperature

11: 97 percent / MCPBA, NaHCO₃ / CH₂Cl₂ / 16 h / Ambient temperature

12: 85 percent / n-BuLi / tetrahydrofuran / 16 h / Ambient temperature

With 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

upstream raw materials:

diphenyl diselenide

((1aR,3R,3aR,6aR,6bR)-5,5-Dimethyl-hexahydro-1,4,6-trioxa-cyclopropa[e]inden-3-yl)-carbamic acid tert-butyl ester

N-tert-butyloxycarbonyl-pyrrole

((1R,5S,6R)-5,6-Dihydroxy-cyclohex-3-enyl)-carbamic acid tert-butyl ester

Downstream raw materials:

(-)-conduramine C₁