5,6-dihydro-5(S)-(2-hydroxyethyl)-2(S)-isopropyloxy-6(R)-<2-(4-methoxybenzyloxy)-1(S)-methyl-1(S)-ethyl>-3-methyl-2H-pyran

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Chemical Name:5,6-dihydro-5(S)-(2-hydroxyethyl)-2(S)-isopropyloxy-6(R)-<2-(4-methoxybenzyloxy)-1(S)-methyl-1(S)-ethyl>-3-methyl-2H-pyran
CAS No.:96181-78-1
Molecular Formula:C₂₂H₃₄O₅
Molecular Weight:378.509
Hs Code.:

Synonyms:5,6-dihydro-5(S)-(2-hydroxyethyl)-2(S)-isopropyloxy-6(R)-<2-(4-methoxybenzyloxy)-1(S)-methyl-1(S)-ethyl>-3-methyl-2H-pyran

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Chemical Property of 5,6-dihydro-5(S)-(2-hydroxyethyl)-2(S)-isopropyloxy-6(R)-<2-(4-methoxybenzyloxy)-1(S)-methyl-1(S)-ethyl>-3-methyl-2H-pyran

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Technology Process of 5,6-dihydro-5(S)-(2-hydroxyethyl)-2(S)-isopropyloxy-6(R)-<2-(4-methoxybenzyloxy)-1(S)-methyl-1(S)-ethyl>-3-methyl-2H-pyran

There total 19 articles about 5,6-dihydro-5(S)-(2-hydroxyethyl)-2(S)-isopropyloxy-6(R)-<2-(4-methoxybenzyloxy)-1(S)-methyl-1(S)-ethyl>-3-methyl-2H-pyran 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: 93.0%

: 96181-86-1
(2S,5S,6S)-2-benzyloxyethyl-5,6-dihydro-2-isopropyloxy-6-<2-(4-methoxybenzyloxy)-1(S)-methylethyl>-3-methyl-2H-pyran

: 96181-78-1
5,6-dihydro-5(S)-(2-hydroxyethyl)-2(S)-isopropyloxy-6(R)-<2-(4-methoxybenzyloxy)-1(S)-methyl-1(S)-ethyl>-3-methyl-2H-pyran

Guidance literature:: With hydrogen; W-2 Raney Ni; In ethanol; for 24h; Ambient temperature;
DOI:10.1016/S0040-4020(01)90593-9

Reference yield:

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

: 96181-78-1
5,6-dihydro-5(S)-(2-hydroxyethyl)-2(S)-isopropyloxy-6(R)-<2-(4-methoxybenzyloxy)-1(S)-methyl-1(S)-ethyl>-3-methyl-2H-pyran

Guidance literature:: Multi-step reaction with 16 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

11: 81 percent / NaIO₄ / H₂O; methanol / 2 h

12: NaH / tetrahydrofuran / 1.) 0 deg C; 2.) -90 to -10 deg C, 5 h

13: K₂CO₃ / methanol / 10 h / Ambient temperature

14: DIBAH / hexane; toluene / 1 h / -80 °C

15: CSA / 1 h / Ambient temperature

16: 79 percent / H₂ / Raney Ni W-2 / 48 h

With 1H-imidazole; hydrogenchloride; sodium periodate; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; sulfuric acid; camphor-10-sulfonic acid; hydrogen; sodium hydride; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; diethylamine; triethylamine; platinum on activated charcoal; Raney Ni W-2; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; water; dimethyl sulfoxide; toluene;
DOI:10.1248/cpb.35.2209

Reference yield:

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

: 96181-78-1
5,6-dihydro-5(S)-(2-hydroxyethyl)-2(S)-isopropyloxy-6(R)-<2-(4-methoxybenzyloxy)-1(S)-methyl-1(S)-ethyl>-3-methyl-2H-pyran

Guidance literature:: Multi-step reaction with 15 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

10: 81 percent / NaIO₄ / H₂O; methanol / 2 h

11: NaH / tetrahydrofuran / 1.) 0 deg C; 2.) -90 to -10 deg C, 5 h

12: K₂CO₃ / methanol / 10 h / Ambient temperature

13: DIBAH / hexane; toluene / 1 h / -80 °C

14: CSA / 1 h / Ambient temperature

15: 79 percent / H₂ / Raney Ni W-2 / 48 h

With 1H-imidazole; hydrogenchloride; sodium periodate; n-butyllithium; oxalyl dichloride; sulfuric acid; camphor-10-sulfonic acid; hydrogen; sodium hydride; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; diethylamine; triethylamine; platinum on activated charcoal; Raney Ni W-2; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; water; dimethyl sulfoxide; toluene;
DOI:10.1248/cpb.35.2209