(9H-fluoren-9-yl)methyl (1S,3S,4R)-1-allyl-4-(benzyloxy)-7-chloro-3-(hydroxymethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

Base Information

Chemical Name:(9H-fluoren-9-yl)methyl (1S,3S,4R)-1-allyl-4-(benzyloxy)-7-chloro-3-(hydroxymethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate
CAS No.:1307772-11-7
Molecular Formula:C₃₅H₃₂ClNO₄
Molecular Weight:566.096
Hs Code.:

Synonyms:(9H-fluoren-9-yl)methyl (1S,3S,4R)-1-allyl-4-(benzyloxy)-7-chloro-3-(hydroxymethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

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Chemical Property of (9H-fluoren-9-yl)methyl (1S,3S,4R)-1-allyl-4-(benzyloxy)-7-chloro-3-(hydroxymethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

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Technology Process of (9H-fluoren-9-yl)methyl (1S,3S,4R)-1-allyl-4-(benzyloxy)-7-chloro-3-(hydroxymethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

There total 6 articles about (9H-fluoren-9-yl)methyl (1S,3S,4R)-1-allyl-4-(benzyloxy)-7-chloro-3-(hydroxymethyl)-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: 91.0%

: 1307771-78-3
(1R,4R,5S)-8-(9H-fluoren-9-yl)methyloxycarbonyl-4-(benzyloxy)-2,3-(3'-chlorobenzo)-7-oxa-8-azabicyclo[3.2.1]octane

: 762-72-1
allyl-trimethyl-silane

: 1307772-11-7
(9H-fluoren-9-yl)methyl (1S,3S,4R)-1-allyl-4-(benzyloxy)-7-chloro-3-(hydroxymethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

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

Reference yield:

: 174265-12-4
2-bromo-5-chlorobenzaldehyde

: 1307772-11-7
(9H-fluoren-9-yl)methyl (1S,3S,4R)-1-allyl-4-(benzyloxy)-7-chloro-3-(hydroxymethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

1.1: toluene-4-sulfonic acid / toluene / Reflux

2.1: iodine; magnesium / tetrahydrofuran / Reflux

2.2: 2 h / -78 °C

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

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

5.1: dichloromethane / 20 °C

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

With hydrogenchloride; iodine; sodium hydride; toluene-4-sulfonic acid; magnesium; ytterbium(III) triflate; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; toluene; mineral oil;
DOI:10.1002/chem.201002938

Reference yield:

: 2-(2-bromo-5-chlorophenyl)-1,3-dioxane

: 1307772-11-7
(9H-fluoren-9-yl)methyl (1S,3S,4R)-1-allyl-4-(benzyloxy)-7-chloro-3-(hydroxymethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1.1: iodine; magnesium / tetrahydrofuran / Reflux

1.2: 2 h / -78 °C

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

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

4.1: dichloromethane / 20 °C

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

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