(1S,2R,3S,4R,4aS,11bR)-4-benzylamino-1,2,3-trihydroxy-2,3,4,4a,6,11b-hexahydro-1H-5,8,10-trioxa-cyclopenta[b]phenanthrene-6-one

Base Information

Chemical Name:(1S,2R,3S,4R,4aS,11bR)-4-benzylamino-1,2,3-trihydroxy-2,3,4,4a,6,11b-hexahydro-1H-5,8,10-trioxa-cyclopenta[b]phenanthrene-6-one
CAS No.:410527-41-2
Molecular Formula:C₂₁H₂₁NO₇
Molecular Weight:399.4
Hs Code.:

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Chemical Property of (1S,2R,3S,4R,4aS,11bR)-4-benzylamino-1,2,3-trihydroxy-2,3,4,4a,6,11b-hexahydro-1H-5,8,10-trioxa-cyclopenta[b]phenanthrene-6-one

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Technology Process of (1S,2R,3S,4R,4aS,11bR)-4-benzylamino-1,2,3-trihydroxy-2,3,4,4a,6,11b-hexahydro-1H-5,8,10-trioxa-cyclopenta[b]phenanthrene-6-one

There total 14 articles about (1S,2R,3S,4R,4aS,11bR)-4-benzylamino-1,2,3-trihydroxy-2,3,4,4a,6,11b-hexahydro-1H-5,8,10-trioxa-cyclopenta[b]phenanthrene-6-one 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:

: C₂₄H₂₅NO₇

: 410527-41-2
(1S,2R,3S,4R,4aS,11bR)-4-benzylamino-1,2,3-trihydroxy-2,3,4,4a,6,11b-hexahydro-1H-5,8,10-trioxa-cyclopenta[b]phenanthrene-6-one

Guidance literature:: With toluene-4-sulfonic acid; In methanol; at 20 ℃; for 38h;
DOI:10.1139/v01-139

Reference yield:

: 130669-75-9
(3aS,7aS)-4-bromo-2,2-dimethyl-3a,7a-dihydro-1,3-benzodioxole

: 410527-41-2
(1S,2R,3S,4R,4aS,11bR)-4-benzylamino-1,2,3-trihydroxy-2,3,4,4a,6,11b-hexahydro-1H-5,8,10-trioxa-cyclopenta[b]phenanthrene-6-one

Guidance literature:: Multi-step reaction with 13 steps

1: Cu(acac)2 / acetonitrile / 20 °C

2: 78 percent / Bu₃SnH; AIBN / tetrahydrofuran / Heating

3: 80 percent / mCPBA; 3-tert-butyl-4-hydroxy-5-methylphenyl sulfide / 1,2-dichloro-ethane / 12 h / Heating

4: KH; 18-crown-6 / 1,2-dimethoxy-ethane / 20 h / 20 °C

5: 71 percent / NaH; Bu₄NI / tetrahydrofuran / 44 h / 20 °C

6: 77 percent / Me₂AlCl / CH₂Cl₂; hexane / 2 h / -25 °C

7: 78 percent / DDQ / CH₂Cl₂ / 23 h / 20 °C

8: NaH / ethanol / 5 h / Heating

9: 163 mg / Na-naphthalene / 1,2-dimethoxy-ethane / 0.5 h / -50 °C

10: CSA / tetrahydrofuran; H₂O / 21 h / 20 °C

11: 131 mg / 3 Angstroem MS; PCC / CH₂Cl₂ / 3 h / 20 °C

12: C₆H₅COONa / methanol; H₂O / 17 h / Heating

13: 9.9 mg / p-toluenesulfonic acid / methanol / 38 h / 20 °C

With sodium benzoate; copper acetylacetonate; 18-crown-6 ether; 2,2'-azobis(isobutyronitrile); 3 Angstroem MS; Na-naphthalene; 6,6'-di-tert-butyl-4,4'-thiodi-o-cresol; camphor-10-sulfonic acid; tri-n-butyl-tin hydride; dimethylaluminum chloride; tetra-(n-butyl)ammonium iodide; potassium hydride; sodium hydride; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; ethanol; hexane; dichloromethane; water; 1,2-dichloro-ethane; acetonitrile;
DOI:10.1139/v01-139

Reference yield:

: 67451-62-1,82683-92-9,132958-32-8,130792-45-9
cis-(1S,2S)-1,2-dihydroxy-3-bromocyclohexa-3,5-diene

: 410527-41-2
(1S,2R,3S,4R,4aS,11bR)-4-benzylamino-1,2,3-trihydroxy-2,3,4,4a,6,11b-hexahydro-1H-5,8,10-trioxa-cyclopenta[b]phenanthrene-6-one

Guidance literature:: Multi-step reaction with 14 steps

1: p-TSA / acetone / 20 °C

2: Cu(acac)2 / acetonitrile / 20 °C

3: 78 percent / Bu₃SnH; AIBN / tetrahydrofuran / Heating

4: 80 percent / mCPBA; 3-tert-butyl-4-hydroxy-5-methylphenyl sulfide / 1,2-dichloro-ethane / 12 h / Heating

5: KH; 18-crown-6 / 1,2-dimethoxy-ethane / 20 h / 20 °C

6: 71 percent / NaH; Bu₄NI / tetrahydrofuran / 44 h / 20 °C

7: 77 percent / Me₂AlCl / CH₂Cl₂; hexane / 2 h / -25 °C

8: 78 percent / DDQ / CH₂Cl₂ / 23 h / 20 °C

9: NaH / ethanol / 5 h / Heating

10: 163 mg / Na-naphthalene / 1,2-dimethoxy-ethane / 0.5 h / -50 °C

11: CSA / tetrahydrofuran; H₂O / 21 h / 20 °C

12: 131 mg / 3 Angstroem MS; PCC / CH₂Cl₂ / 3 h / 20 °C

13: C₆H₅COONa / methanol; H₂O / 17 h / Heating

14: 9.9 mg / p-toluenesulfonic acid / methanol / 38 h / 20 °C

With sodium benzoate; copper acetylacetonate; 18-crown-6 ether; 2,2'-azobis(isobutyronitrile); 3 Angstroem MS; Na-naphthalene; 6,6'-di-tert-butyl-4,4'-thiodi-o-cresol; camphor-10-sulfonic acid; tri-n-butyl-tin hydride; dimethylaluminum chloride; tetra-(n-butyl)ammonium iodide; potassium hydride; sodium hydride; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; ethanol; hexane; dichloromethane; water; 1,2-dichloro-ethane; acetone; acetonitrile;
DOI:10.1139/v01-139