2H-Pyran-2-ol, 5,6-dihydro-6-[2-[(4-methoxyphenyl)methoxy]-1-methylethyl]-3-methyl-5-[ 2-(phenylmethoxy)ethyl]-

Base Information

• Chemical Name: 2H-Pyran-2-ol, 5,6-dihydro-6-[2-[(4-methoxyphenyl)methoxy]-1-methylethyl]-3-methyl-5-[ 2-(phenylmethoxy)ethyl]-
• CAS No.: 113918-98-2
• Molecular Formula: C₂₆H₃₄O₅
• Molecular Weight: 426.553

Synonyms:

Chemical Property of 2H-Pyran-2-ol, 5,6-dihydro-6-[2-[(4-methoxyphenyl)methoxy]-1-methylethyl]-3-methyl-5-[ 2-(phenylmethoxy)ethyl]-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2H-Pyran-2-ol, 5,6-dihydro-6-[2-[(4-methoxyphenyl)methoxy]-1-methylethyl]-3-methyl-5-[ 2-(phenylmethoxy)ethyl]-

There total 16 articles about 2H-Pyran-2-ol, 5,6-dihydro-6-[2-[(4-methoxyphenyl)methoxy]-1-methylethyl]-3-methyl-5-[ 2-(phenylmethoxy)ethyl]- 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:

3-deoxy-3-C-<(ethoxycarbonyl)methyl>-1,2:5,6-di-O-isopropylidene-α-D-allofuranose (58399-55-6) → (2S,5S,6S)-5-(2-Benzyloxy-ethyl)-6-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-3-methyl-5,6-dihydro-2H-pyran-2-ol (113918-98-2)

Guidance literature:

Multi-step reaction with 14 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

With 1H-imidazole; hydrogenchloride; sodium periodate; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; sulfuric acid; hydrogen; sodium hydride; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; diethylamine; triethylamine; platinum on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; water; dimethyl sulfoxide; toluene;

DOI:10.1248/cpb.35.2209

Reference yield:

1,2;5,6-di-O-isopropylidene-3-(2-hydroxyethyl)-α-D-allofuranoside (18427-19-5) → (2S,5S,6S)-5-(2-Benzyloxy-ethyl)-6-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-3-methyl-5,6-dihydro-2H-pyran-2-ol (113918-98-2)

Guidance literature:

Multi-step reaction with 13 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

With 1H-imidazole; hydrogenchloride; sodium periodate; n-butyllithium; oxalyl dichloride; sulfuric acid; hydrogen; sodium hydride; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; diethylamine; triethylamine; platinum on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; water; dimethyl sulfoxide; toluene;

DOI:10.1248/cpb.35.2209

Reference yield:

(3aR,5S,6R,6aR)-6-[2-(benzyloxy)ethyl]-2,2-dimethyl-5-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]tetrahydrofuro[2,3-d][1,3]dioxole (113918-87-9) → (2S,5S,6S)-5-(2-Benzyloxy-ethyl)-6-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-3-methyl-5,6-dihydro-2H-pyran-2-ol (113918-98-2)

Guidance literature:

Multi-step reaction with 12 steps

1: 2percent H₂SO₄ / methanol / 40 h / Ambient temperature

2: imidazole / CH₂Cl₂ / 3 h / 0 °C

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

4: 84 percent / n-butyllithium / tetrahydrofuran / 1.) room temp., 1 h; 2.) room temp., 3 h

5: 98 percent / 2 N HCl / methanol / 0.25 h / Ambient temperature

6: 50 percent / H₂ / 5percent Pt-C / 3 h

7: 93 percent / NaH,Et₂NH / tetrahydrofuran; dimethylsulfoxide / 1.) room temp., 2 h; 2.) 50 deg C, 3 h

8: 68 percent / 4 N H₂SO₄ / dioxane / 4.5 h / 65 °C

9: 81 percent / NaIO₄ / H₂O; methanol / 2 h

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

11: K₂CO₃ / methanol / 10 h / Ambient temperature

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

With 1H-imidazole; hydrogenchloride; sodium periodate; n-butyllithium; oxalyl dichloride; sulfuric acid; hydrogen; sodium hydride; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; diethylamine; triethylamine; platinum on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; water; dimethyl sulfoxide; toluene;

DOI:10.1248/cpb.35.2209

upstream raw materials:

(2Z,4S,5S,6S)-4-(2-benzyloxyethyl)-5-hydroxy-2,6-dimethyl-7-(4-methoxybenzyloxy)hept-2-enoic acid δ-lactone

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

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

3-C-(2-benzyloxyethyl)-3,5-dideoxy-1,2-O-isopropylidene-5-C-methyl-β-L-talofuranose

Downstream raw materials:

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

5(R)-(2-hydroxyethyl)-2(S)-isopropyloxy-6(S)-<2-(4-methoxybenzyloxy)-1(S)-methyl-1(S)-ethyl>-3-(R)-methyl-tetrahydropyran

5(R)-(2-hydroxyethyl)-2(S)-isopropyloxy-6(S)-<2-(4-methoxybenzyloxy)-1(S)-methyl-1(S)-ethyl>-3-(S)-methyl-tetrahydropyran

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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