(9H-fluoren-9-yl)methyl (1S,3S,4R)-4-(benzyloxy)-3-(hydroxymethyl)-1-(1H-indol-3-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

Base Information

Chemical Name:(9H-fluoren-9-yl)methyl (1S,3S,4R)-4-(benzyloxy)-3-(hydroxymethyl)-1-(1H-indol-3-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate
CAS No.:1307772-27-5
Molecular Formula:C₄₀H₃₄N₂O₄
Molecular Weight:606.721
Hs Code.:

Synonyms:(9H-fluoren-9-yl)methyl (1S,3S,4R)-4-(benzyloxy)-3-(hydroxymethyl)-1-(1H-indol-3-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

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Chemical Property of (9H-fluoren-9-yl)methyl (1S,3S,4R)-4-(benzyloxy)-3-(hydroxymethyl)-1-(1H-indol-3-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

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Technology Process of (9H-fluoren-9-yl)methyl (1S,3S,4R)-4-(benzyloxy)-3-(hydroxymethyl)-1-(1H-indol-3-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

There total 8 articles about (9H-fluoren-9-yl)methyl (1S,3S,4R)-4-(benzyloxy)-3-(hydroxymethyl)-1-(1H-indol-3-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate 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: 89.0%

: 120-72-9
indole

: 1307771-59-0
(1R,4R,5S)-8-((9H-fluoren-9-yl)methyloxycarbonyl)-4-(benzyloxy)-2,3-benzo-7-oxa-8-azabicyclo[3.2.1]octane

: 1307772-27-5
(9H-fluoren-9-yl)methyl (1S,3S,4R)-4-(benzyloxy)-3-(hydroxymethyl)-1-(1H-indol-3-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

: 1307772-03-7
(9H-fluoren-9-yl)methyl (1R,3S,4R)-4-(benzyloxy)-3-(hydroxymethyl)-1-(1H-indol-3-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

Guidance literature:: With ytterbium(III) triflate; In dichloromethane; at -20 - 20 ℃; optical yield given as %de; diastereoselective reaction;
DOI:10.1002/chem.201002938

Reference yield:

: 1307770-68-8
tert-butyl (4S)-4-((R)-(2-(1,3-dioxan-2-yl)phenyl)(benzyloxy)methyl)-2,2-dimethyloxazolidine-3-carboxylate

: 1307772-27-5
(9H-fluoren-9-yl)methyl (1S,3S,4R)-4-(benzyloxy)-3-(hydroxymethyl)-1-(1H-indol-3-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

: 1307772-03-7
(9H-fluoren-9-yl)methyl (1R,3S,4R)-4-(benzyloxy)-3-(hydroxymethyl)-1-(1H-indol-3-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: hydrogenchloride / tetrahydrofuran; water / 2 h / 20 °C

2: dichloromethane / 20 °C

3: ytterbium(III) triflate / dichloromethane / -20 - 20 °C

With hydrogenchloride; ytterbium(III) triflate; In tetrahydrofuran; dichloromethane; water;
DOI:10.1002/chem.201002938

Reference yield:

: C₂₁H₃₁NO₆

: 1307772-27-5
(9H-fluoren-9-yl)methyl (1S,3S,4R)-4-(benzyloxy)-3-(hydroxymethyl)-1-(1H-indol-3-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

: 1307772-03-7
(9H-fluoren-9-yl)methyl (1R,3S,4R)-4-(benzyloxy)-3-(hydroxymethyl)-1-(1H-indol-3-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 3 h / 0 °C

2: hydrogenchloride / tetrahydrofuran; water / 2 h / 20 °C

3: dichloromethane / 20 °C

4: ytterbium(III) triflate / dichloromethane / -20 - 20 °C

With hydrogenchloride; sodium hydride; ytterbium(III) triflate; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; mineral oil;
DOI:10.1002/chem.201002938