(E)-6β-(hydroxymethyl)-12-<2-((tert-butyldimethylsilyl)oxy)ethylidene>-7-((4-methoxyphenyl)sulfonyl)-1,2,3aβ,4,5β,6,6a,7-octahydro-3,5-ethano-3H-pyrrolo<2,3-d>carbazole

Base Information

Chemical Name:(E)-6β-(hydroxymethyl)-12-<2-((tert-butyldimethylsilyl)oxy)ethylidene>-7-((4-methoxyphenyl)sulfonyl)-1,2,3aβ,4,5β,6,6a,7-octahydro-3,5-ethano-3H-pyrrolo<2,3-d>carbazole
CAS No.:141321-47-3
Molecular Formula:C₃₂H₄₄N₂O₅SSi
Molecular Weight:596.863
Hs Code.:

(E)-6β-(hydroxymethyl)-12-<2-((tert-butyldimethylsilyl)oxy)ethylidene>-7-((4-methoxyphenyl)sulfonyl)-1,2,3aβ,4,5β,6,6a,7-octahydro-3,5-ethano-3H-pyrrolo<2,3-d>carbazole

Synonyms:(E)-6β-(hydroxymethyl)-12-<2-((tert-butyldimethylsilyl)oxy)ethylidene>-7-((4-methoxyphenyl)sulfonyl)-1,2,3aβ,4,5β,6,6a,7-octahydro-3,5-ethano-3H-pyrrolo<2,3-d>carbazole

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Chemical Property of (E)-6β-(hydroxymethyl)-12-<2-((tert-butyldimethylsilyl)oxy)ethylidene>-7-((4-methoxyphenyl)sulfonyl)-1,2,3aβ,4,5β,6,6a,7-octahydro-3,5-ethano-3H-pyrrolo<2,3-d>carbazole

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Technology Process of (E)-6β-(hydroxymethyl)-12-<2-((tert-butyldimethylsilyl)oxy)ethylidene>-7-((4-methoxyphenyl)sulfonyl)-1,2,3aβ,4,5β,6,6a,7-octahydro-3,5-ethano-3H-pyrrolo<2,3-d>carbazole

There total 1 articles about (E)-6β-(hydroxymethyl)-12-<2-((tert-butyldimethylsilyl)oxy)ethylidene>-7-((4-methoxyphenyl)sulfonyl)-1,2,3aβ,4,5β,6,6a,7-octahydro-3,5-ethano-3H-pyrrolo<2,3-d>carbazole 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: 60.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 141321-46-2
(E)-6β-(hydroxymethyl)-12-(2-hydroxyethylidene)-7-((4-methoxyphenyl)sulfonyl)-1,2,3aβ,4,5β,6,6a,7-octahydro-3,5-ethano-3H-pyrrolo<2,3-d>carbazole

: 141321-47-3
(E)-6β-(hydroxymethyl)-12-<2-((tert-butyldimethylsilyl)oxy)ethylidene>-7-((4-methoxyphenyl)sulfonyl)-1,2,3aβ,4,5β,6,6a,7-octahydro-3,5-ethano-3H-pyrrolo<2,3-d>carbazole

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at -20 ℃;
DOI:10.1021/ja00071a025

Reference yield: 70.0%

: 141321-47-3
(E)-6β-(hydroxymethyl)-12-<2-((tert-butyldimethylsilyl)oxy)ethylidene>-7-((4-methoxyphenyl)sulfonyl)-1,2,3aβ,4,5β,6,6a,7-octahydro-3,5-ethano-3H-pyrrolo<2,3-d>carbazole

: 141321-48-4
(E)-6β-formyl-12-<2-((tert-butyldimethylsilyl)oxy)ethylidene>-7-((4-methoxyphenyl)sulfonyl)-1,2,3aβ,4,5β,6,6a,7-octahydro-3,5-ethano-3H-pyrrolo<2,3-d>carbazole

Guidance literature:: With pyridine-SO₃ complex; dimethyl sulfoxide; triethylamine; at 25 ℃; for 4h;
DOI:10.1021/ja00071a025

Reference yield:

: 141321-47-3
(E)-6β-(hydroxymethyl)-12-<2-((tert-butyldimethylsilyl)oxy)ethylidene>-7-((4-methoxyphenyl)sulfonyl)-1,2,3aβ,4,5β,6,6a,7-octahydro-3,5-ethano-3H-pyrrolo<2,3-d>carbazole

: 141321-46-2
(E)-6β-(hydroxymethyl)-12-(2-hydroxyethylidene)-7-((4-methoxyphenyl)sulfonyl)-1,2,3aβ,4,5β,6,6a,7-octahydro-3,5-ethano-3H-pyrrolo<2,3-d>carbazole

Guidance literature:: Multi-step reaction with 9 steps

1: 70 percent / SO₃*pyridine, triethylamine, DMSO / 4 h / 25 °C

2: 60 percent / pyridine*HF/pyridine / 2 h / 0 °C

3: 72 percent / N-methylmorpholine N-oxide, osmium tetroxide / 2-methyl-propan-2-ol; tetrahydrofuran; H₂O / 2 h / 25 °C

4: 56 percent / lithium borohydride / tetrahydrofuran / 16 h / Heating

5: trifluoroacetic acid, periodic acid / methanol; H₂O / 3 h / 25 °C

6: 69 percent / DBU / CH₂Cl₂ / 0.5 h / 25 °C

7: 1.) potassium hexamethyldisilazide / 1.) THF, 25 deg C, 20 min, 2.) THF, 25 deg C, 42 h

8: 31 percent / DIBAL / CH₂Cl₂ / 0.33 h / 25 °C

9: 81 percent / 2 N HCl / methanol / 15 h

With pyridine; hydrogenchloride; osmium(VIII) oxide; lithium borohydride; pyridine-SO₃ complex; potassium hexamethylsilazane; diisobutylaluminium hydride; pyridine hydrogenfluoride; dimethyl sulfoxide; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; periodic acid; triethylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; water; tert-butyl alcohol;
DOI:10.1021/ja00071a025