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

Base Information

Chemical Name:(2S,3S,4S)-4-hydroxy-2-[(R)-hydroxy(1-naphthyl)methyl]-4-(p-methoxybenzyloxy)-3-(p-methoxybenzyloxymethyl)tetrahydrofuran
CAS No.:501012-29-9
Molecular Formula:C₃₂H₃₄O₇
Molecular Weight:530.618
Hs Code.:

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

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

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

There total 12 articles about (2S,3S,4S)-4-hydroxy-2-[(R)-hydroxy(1-naphthyl)methyl]-4-(p-methoxybenzyloxy)-3-(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: 95.0%

: 90-11-9
1-Bromonaphthalene

: 501012-25-5
(2R,3S,4S)-4-hydroxy-3-(p-methoxybenzyloxy)-4-(p-methoxybenzyloxymethyl)tetrahydrofuran-2-carbaldehyde

: 501012-29-9
(2S,3S,4S)-4-hydroxy-2-[(R)-hydroxy(1-naphthyl)methyl]-4-(p-methoxybenzyloxy)-3-(p-methoxybenzyloxymethyl)tetrahydrofuran

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

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

Reference yield:

: 225233-48-7
4-C-hydroxymethyl-1,2-O-isopropylidene-3,5-di-O-p-methoxybenzyl-α-D-ribo-pentofuranose

: 501012-29-9
(2S,3S,4S)-4-hydroxy-2-[(R)-hydroxy(1-naphthyl)methyl]-4-(p-methoxybenzyloxy)-3-(p-methoxybenzyloxymethyl)tetrahydrofuran

Guidance literature:: Multi-step reaction with 5 steps

1.1: 89 percent / pyridine / 20 °C

2.1: aq. HCl / 72 h / 20 °C

3.1: NaH / dimethylformamide; various solvent(s) / 12 h / 20 °C

4.1: 82 percent / aq. AcOH / 4 h / 50 °C

5.1: Mg; I₂ / tetrahydrofuran / 1 h / 40 °C

5.2: 95 percent / tetrahydrofuran / 12 h / 20 °C

With pyridine; hydrogenchloride; iodine; sodium hydride; magnesium; acetic acid; In tetrahydrofuran; N,N-dimethyl-formamide; 5.2: Grignard reaction;

Reference yield:

: 501012-23-3
4-C-methanesulfonyloxymethyl-3,5-di-O-(p-methoxybenzyl)-1,2-O-isopropylidene-α-D-ribofuranose

: 501012-29-9
(2S,3S,4S)-4-hydroxy-2-[(R)-hydroxy(1-naphthyl)methyl]-4-(p-methoxybenzyloxy)-3-(p-methoxybenzyloxymethyl)tetrahydrofuran

Guidance literature:: Multi-step reaction with 4 steps

1.1: aq. HCl / 72 h / 20 °C

2.1: NaH / dimethylformamide; various solvent(s) / 12 h / 20 °C

3.1: 82 percent / aq. AcOH / 4 h / 50 °C

4.1: Mg; I₂ / tetrahydrofuran / 1 h / 40 °C

4.2: 95 percent / tetrahydrofuran / 12 h / 20 °C

With hydrogenchloride; iodine; sodium hydride; magnesium; acetic acid; In tetrahydrofuran; N,N-dimethyl-formamide; 4.2: Grignard reaction;