(2R,3R,4R)-4-hydroxy-2-[(S)-hydroxy(1-pyrenyl)methyl]-3-(p-methoxybenzyloxy)-4-(p-methoxybenzyloxymethyl)tetrahydrofuran

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Chemical Name:(2R,3R,4R)-4-hydroxy-2-[(S)-hydroxy(1-pyrenyl)methyl]-3-(p-methoxybenzyloxy)-4-(p-methoxybenzyloxymethyl)tetrahydrofuran
CAS No.:676126-66-2
Molecular Formula:C₃₈H₃₆O₇
Molecular Weight:604.7
Hs Code.:

Synonyms:(2R,3R,4R)-4-hydroxy-2-[(S)-hydroxy(1-pyrenyl)methyl]-3-(p-methoxybenzyloxy)-4-(p-methoxybenzyloxymethyl)tetrahydrofuran

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Chemical Property of (2R,3R,4R)-4-hydroxy-2-[(S)-hydroxy(1-pyrenyl)methyl]-3-(p-methoxybenzyloxy)-4-(p-methoxybenzyloxymethyl)tetrahydrofuran

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Technology Process of (2R,3R,4R)-4-hydroxy-2-[(S)-hydroxy(1-pyrenyl)methyl]-3-(p-methoxybenzyloxy)-4-(p-methoxybenzyloxymethyl)tetrahydrofuran

There total 14 articles about (2R,3R,4R)-4-hydroxy-2-[(S)-hydroxy(1-pyrenyl)methyl]-3-(p-methoxybenzyloxy)-4-(p-methoxybenzyloxymethyl)tetrahydrofuran 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: 71.0%

: 1714-29-0
1-bromopyrene

: 676126-64-0
(2S,3R,4R)-4-hydroxy-3-(p-methoxybenzyloxy)-4-(p-methoxybenzyloxymethyl)tetrahydrofuran-2-carbaldehyde

: 676126-66-2
(2R,3R,4R)-4-hydroxy-2-[(S)-hydroxy(1-pyrenyl)methyl]-3-(p-methoxybenzyloxy)-4-(p-methoxybenzyloxymethyl)tetrahydrofuran

Guidance literature:: 1-bromopyrene; With iodine; magnesium; In tetrahydrofuran; at 40 ℃; for 1h;

(2S,3R,4R)-4-hydroxy-3-(p-methoxybenzyloxy)-4-(p-methoxybenzyloxymethyl)tetrahydrofuran-2-carbaldehyde; In tetrahydrofuran; at 20 ℃; for 12h; Further stages.;
DOI:10.1039/b310719a

Reference yield:

: 676126-68-4
(2S,3R,4R)-4-hydroxy-2-(1-pyrenylcarbonyl)-3-(p-methoxybenzyloxy)-4-(p-methoxybenzyloxymethyl)tetrahydrofuran

: 676126-66-2
(2R,3R,4R)-4-hydroxy-2-[(S)-hydroxy(1-pyrenyl)methyl]-3-(p-methoxybenzyloxy)-4-(p-methoxybenzyloxymethyl)tetrahydrofuran

: 676126-70-8
(2R,3R,4R)-4-hydroxy-2-[(R)-hydroxy(1-pyrenyl)methyl]-3-(p-methoxybenzyloxy)-4-(p-methoxybenzyloxymethyl)tetrahydrofuran

Guidance literature:: With sodium tetrahydroborate; In tetrahydrofuran; at 20 ℃; for 0.5h;
DOI:10.1039/b310719a

Reference yield:

: 109536-51-8,142226-16-2,69940-04-1
1,2-O-isopropylidene-3-O-(4-methoxybenzyl)-α-D-glucofuranose

: 676126-66-2
(2R,3R,4R)-4-hydroxy-2-[(S)-hydroxy(1-pyrenyl)methyl]-3-(p-methoxybenzyloxy)-4-(p-methoxybenzyloxymethyl)tetrahydrofuran

Guidance literature:: Multi-step reaction with 11 steps

1.1: aq. NaIO₄ / tetrahydrofuran / 12 h / 20 °C

1.2: 87 percent / aq. NaOH / dioxane / 24 h / 20 °C

2.1: 93 percent / pyridine / CH₂Cl₂ / 12 h / 20 °C

3.1: 83 percent / aq. HCl / 36 h / 20 °C

4.1: pyridine / CH₂Cl₂ / 12 h / 20 °C

5.1: 18-crown-6-ether / CH₂Cl₂; toluene / 12 h / 50 °C

6.1: ammonia / methanol / 24 h / 20 °C

6.2: NaH / dimethylformamide / 12 h / 20 °C

7.1: 18-crown-6 / dioxane / 12 h / Heating

8.1: ammonia / methanol / 12 h / 20 °C

9.1: NaH / tetrahydrofuran / 0.25 h / 20 °C

9.2: tetrabutylammonium iodide / tetrahydrofuran / 36 h / 20 °C

10.1: aq. AcOH / 12 h / 20 °C

11.1: magnesium; iodine / tetrahydrofuran / 1 h / 40 °C

11.2: 71 percent / tetrahydrofuran / 12 h / 20 °C

With pyridine; hydrogenchloride; sodium periodate; 18-crown-6 ether; ammonia; iodine; sodium hydride; magnesium; acetic acid; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; toluene; 1.2: Cannizzaro reaction / 11.2: Grignard addition;
DOI:10.1039/b310719a