(2S,3R,4S,5R)-4-(2-Benzyloxy-ethyl)-5-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-tetrahydro-furan-2,3-diol

Base Information

Chemical Name:(2S,3R,4S,5R)-4-(2-Benzyloxy-ethyl)-5-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-tetrahydro-furan-2,3-diol
CAS No.:113918-95-9
Molecular Formula:C₂₄H₃₂O₆
Molecular Weight:416.514
Hs Code.:

Synonyms:(2S,3R,4S,5R)-4-(2-Benzyloxy-ethyl)-5-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-tetrahydro-furan-2,3-diol

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Chemical Property of (2S,3R,4S,5R)-4-(2-Benzyloxy-ethyl)-5-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-tetrahydro-furan-2,3-diol

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Technology Process of (2S,3R,4S,5R)-4-(2-Benzyloxy-ethyl)-5-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-tetrahydro-furan-2,3-diol

There total 12 articles about (2S,3R,4S,5R)-4-(2-Benzyloxy-ethyl)-5-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-tetrahydro-furan-2,3-diol 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: 68.0%

: 113918-94-8
3-C-(2-benzyloxyethyl)-3,5-dideoxy-1,2-O-isopropylidene-6-O-(4-methoxybenzyl)-5-C-methyl-β-D-talofuranose

: 113918-95-9
(2S,3R,4S,5R)-4-(2-Benzyloxy-ethyl)-5-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-tetrahydro-furan-2,3-diol

Guidance literature:: With sulfuric acid; In 1,4-dioxane; at 65 ℃; for 4.5h;
DOI:10.1248/cpb.35.2209

Reference yield:

: 58399-55-6
3-deoxy-3-C-<(ethoxycarbonyl)methyl>-1,2:5,6-di-O-isopropylidene-α-D-allofuranose

: 113918-95-9
(2S,3R,4S,5R)-4-(2-Benzyloxy-ethyl)-5-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-tetrahydro-furan-2,3-diol

Guidance literature:: Multi-step reaction with 10 steps

1: LAH / tetrahydrofuran / Ambient temperature

2: NaH / tetrahydrofuran; dimethylsulfoxide / 4 h / Ambient temperature

3: 2percent H₂SO₄ / methanol / 40 h / Ambient temperature

4: imidazole / CH₂Cl₂ / 3 h / 0 °C

5: 1.) oxalyl chloride/DMSO 2.) Et₃N / 1.) CHCl₂, -70 deg C; 2.) CH₂Cl₂, -70 to 0 deg C

6: 84 percent / n-butyllithium / tetrahydrofuran / 1.) room temp., 1 h; 2.) room temp., 3 h

7: 98 percent / 2 N HCl / methanol / 0.25 h / Ambient temperature

8: 50 percent / H₂ / 5percent Pt-C / 3 h

9: 93 percent / NaH,Et₂NH / tetrahydrofuran; dimethylsulfoxide / 1.) room temp., 2 h; 2.) 50 deg C, 3 h

10: 68 percent / 4 N H₂SO₄ / dioxane / 4.5 h / 65 °C

With 1H-imidazole; hydrogenchloride; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; sulfuric acid; hydrogen; sodium hydride; dimethyl sulfoxide; diethylamine; triethylamine; platinum on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; dimethyl sulfoxide;
DOI:10.1248/cpb.35.2209

Reference yield:

: 18427-19-5
1,2;5,6-di-O-isopropylidene-3-(2-hydroxyethyl)-α-D-allofuranoside

: 113918-95-9
(2S,3R,4S,5R)-4-(2-Benzyloxy-ethyl)-5-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-tetrahydro-furan-2,3-diol

Guidance literature:: Multi-step reaction with 9 steps

1: NaH / tetrahydrofuran; dimethylsulfoxide / 4 h / Ambient temperature

2: 2percent H₂SO₄ / methanol / 40 h / Ambient temperature

3: imidazole / CH₂Cl₂ / 3 h / 0 °C

4: 1.) oxalyl chloride/DMSO 2.) Et₃N / 1.) CHCl₂, -70 deg C; 2.) CH₂Cl₂, -70 to 0 deg C

5: 84 percent / n-butyllithium / tetrahydrofuran / 1.) room temp., 1 h; 2.) room temp., 3 h

6: 98 percent / 2 N HCl / methanol / 0.25 h / Ambient temperature

7: 50 percent / H₂ / 5percent Pt-C / 3 h

8: 93 percent / NaH,Et₂NH / tetrahydrofuran; dimethylsulfoxide / 1.) room temp., 2 h; 2.) 50 deg C, 3 h

9: 68 percent / 4 N H₂SO₄ / dioxane / 4.5 h / 65 °C

With 1H-imidazole; hydrogenchloride; n-butyllithium; oxalyl dichloride; sulfuric acid; hydrogen; sodium hydride; dimethyl sulfoxide; diethylamine; triethylamine; platinum on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; dimethyl sulfoxide;
DOI:10.1248/cpb.35.2209