(2R,3aS,4S,9bR)-5-(tert-butoxycarbonyl)-8-methoxycarbonyl-4-(tert-butyldimethylsilyloxy)-2-[(tert-butyldiphenylsilyloxy)methyl]-2,3,3a,4-tetrahydro-9bH-pyrrolo[3,2-c]quinoline

Base Information

Chemical Name:(2R,3aS,4S,9bR)-5-(tert-butoxycarbonyl)-8-methoxycarbonyl-4-(tert-butyldimethylsilyloxy)-2-[(tert-butyldiphenylsilyloxy)methyl]-2,3,3a,4-tetrahydro-9bH-pyrrolo[3,2-c]quinoline
CAS No.:929897-59-6
Molecular Formula:C₄₁H₅₈N₂O₆Si₂
Molecular Weight:731.092
Hs Code.:

(2R,3aS,4S,9bR)-5-(tert-butoxycarbonyl)-8-methoxycarbonyl-4-(tert-butyldimethylsilyloxy)-2-[(tert-butyldiphenylsilyloxy)methyl]-2,3,3a,4-tetrahydro-9bH-pyrrolo[3,2-c]quinoline

Synonyms:(2R,3aS,4S,9bR)-5-(tert-butoxycarbonyl)-8-methoxycarbonyl-4-(tert-butyldimethylsilyloxy)-2-[(tert-butyldiphenylsilyloxy)methyl]-2,3,3a,4-tetrahydro-9bH-pyrrolo[3,2-c]quinoline

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Chemical Property of (2R,3aS,4S,9bR)-5-(tert-butoxycarbonyl)-8-methoxycarbonyl-4-(tert-butyldimethylsilyloxy)-2-[(tert-butyldiphenylsilyloxy)methyl]-2,3,3a,4-tetrahydro-9bH-pyrrolo[3,2-c]quinoline

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Technology Process of (2R,3aS,4S,9bR)-5-(tert-butoxycarbonyl)-8-methoxycarbonyl-4-(tert-butyldimethylsilyloxy)-2-[(tert-butyldiphenylsilyloxy)methyl]-2,3,3a,4-tetrahydro-9bH-pyrrolo[3,2-c]quinoline

There total 11 articles about (2R,3aS,4S,9bR)-5-(tert-butoxycarbonyl)-8-methoxycarbonyl-4-(tert-butyldimethylsilyloxy)-2-[(tert-butyldiphenylsilyloxy)methyl]-2,3,3a,4-tetrahydro-9bH-pyrrolo[3,2-c]quinoline 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: 77.0%

: methyl-4-(tert-butylcarbonylamino)-3-{[(6R)-2,2,11,11,12,12-hexamethyl-3,3-diphenyl-4,10-dioxa-3,11-disilatridec-8-en-6-ylimino]methyl}benzoate

: 929897-59-6
(2R,3aS,4S,9bR)-5-(tert-butoxycarbonyl)-8-methoxycarbonyl-4-(tert-butyldimethylsilyloxy)-2-[(tert-butyldiphenylsilyloxy)methyl]-2,3,3a,4-tetrahydro-9bH-pyrrolo[3,2-c]quinoline

: 929897-22-3
C₄₁H₅₈N₂O₆Si₂

Guidance literature:: With perhydrodibenzo-18-crown-6; potassium hydride; In tetrahydrofuran; at 0 - 20 ℃; diastereoselective reaction;
DOI:10.1246/cl.2008.962

Reference yield: 38.0%

: methyl-4-(tert-butylcarbonylamino)-3-{[(6R)-2,2,11,11,12,12-hexamethyl-3,3-diphenyl-4,10-dioxa-3,11-disilatridec-8-en-6-ylimino]methyl}benzoate

: 929897-59-6
(2R,3aS,4S,9bR)-5-(tert-butoxycarbonyl)-8-methoxycarbonyl-4-(tert-butyldimethylsilyloxy)-2-[(tert-butyldiphenylsilyloxy)methyl]-2,3,3a,4-tetrahydro-9bH-pyrrolo[3,2-c]quinoline

: (2R,3aR,9bS)-5-(tert-butoxycarbonyl)-8-methoxycarbonyl-4-(tert-butyldimethylsilyloxy)-2-[(tert-butyldiphenylsilyloxy)methyl]-2,3,3a,4-tetrahydro-9bH-pyrrolo[3,2-c]quinoline

Guidance literature:: With 4 A molecular sieve; boron trifluoride diethyl etherate; In dichloromethane; at -40 - 0 ℃;
DOI:10.1039/b611121a

Reference yield:

: 4-amino-3-[1,3]dioxolan-2-yl-benzoic acid methyl ester

: 929897-59-6
(2R,3aS,4S,9bR)-5-(tert-butoxycarbonyl)-8-methoxycarbonyl-4-(tert-butyldimethylsilyloxy)-2-[(tert-butyldiphenylsilyloxy)methyl]-2,3,3a,4-tetrahydro-9bH-pyrrolo[3,2-c]quinoline

Guidance literature:: Multi-step reaction with 5 steps

1.1: 14.8 g / pyridine / DMAP / CH₂Cl₂ / 15 h

2.1: DMAP / acetonitrile / 2 h / 20 °C

2.2: 99 percent / DEAEA / acetonitrile / 1.5 h

3.1: 99 percent / HCl / tetrahydrofuran / 2.5 h / 20 °C

4.1: 88 percent / molecular sieves 4 Angstroem; LiBF₄ / benzene / 8 h / Heating

5.1: 9 percent / BF₃*OEt₂; molecular sieves 4 Angstroem / CH₂Cl₂ / -40 - 0 °C

With pyridine; hydrogenchloride; lithium tetrafluoroborate; 4 A molecular sieve; boron trifluoride diethyl etherate; dmap; In tetrahydrofuran; dichloromethane; acetonitrile; benzene;
DOI:10.1039/b611121a