1-[(2R,3R,4S,5S,6R)-4-Benzyloxy-6-(2-hydroxy-ethyl)-3,5-dimethyl-tetrahydro-pyran-2-yl]-ethanone

Base Information

• Chemical Name: 1-[(2R,3R,4S,5S,6R)-4-Benzyloxy-6-(2-hydroxy-ethyl)-3,5-dimethyl-tetrahydro-pyran-2-yl]-ethanone
• CAS No.: 308350-54-1
• Molecular Formula: C₁₈H₂₆O₄
• Molecular Weight: 306.402

Synonyms:1-[(2R,3R,4S,5S,6R)-4-Benzyloxy-6-(2-hydroxy-ethyl)-3,5-dimethyl-tetrahydro-pyran-2-yl]-ethanone

Chemical Property of 1-[(2R,3R,4S,5S,6R)-4-Benzyloxy-6-(2-hydroxy-ethyl)-3,5-dimethyl-tetrahydro-pyran-2-yl]-ethanone

Chemical Property:

Purity/Quality:

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Technology Process of 1-[(2R,3R,4S,5S,6R)-4-Benzyloxy-6-(2-hydroxy-ethyl)-3,5-dimethyl-tetrahydro-pyran-2-yl]-ethanone

There total 13 articles about 1-[(2R,3R,4S,5S,6R)-4-Benzyloxy-6-(2-hydroxy-ethyl)-3,5-dimethyl-tetrahydro-pyran-2-yl]-ethanone 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: 89.0%

1-[(2S,3R,4S,5S,6R)-4-Benzyloxy-6-(2-hydroxy-ethyl)-3,5-dimethyl-tetrahydro-pyran-2-yl]-ethanone (308350-53-0) → 1-[(2R,3R,4S,5S,6R)-4-Benzyloxy-6-(2-hydroxy-ethyl)-3,5-dimethyl-tetrahydro-pyran-2-yl]-ethanone (308350-54-1)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; for 48h; Heating;

DOI:10.1002/(SICI)1521-3765(20000915)6:18<3313::AID-CHEM3313>3.0.CO;2-0

Reference yield:

C16H20O2 → 1-[(2R,3R,4S,5S,6R)-4-Benzyloxy-6-(2-hydroxy-ethyl)-3,5-dimethyl-tetrahydro-pyran-2-yl]-ethanone (308350-54-1)

Guidance literature:

Multi-step reaction with 9 steps

1.1: (-)-(Ipc)2BH / tetrahydrofuran / 336 h / -15 °C

1.2: 98 percent / H₂O₂; NaOH / tetrahydrofuran / 3 h

2.1: 96 percent / PCC; SiO₂ / CH₂Cl₂ / 15 h / 20 °C

3.1: m-CPBA; NaHCO₃ / CH₂Cl₂ / 15 h / 20 °C

4.1: 100 percent / TMSOTf / acetonitrile / -40 - -20 °C

5.1: 94 percent / BH₃*THF / CH₂Cl₂ / 3 h / 0 °C

6.1: 100 percent / imidazole; DMAP / CH₂Cl₂ / 15 h / 20 °C

7.1: toluene / 15 h / 20 °C / ultrasound

7.2: 76 percent / aq. HCl / toluene / 0.5 h

8.1: 97 percent / TBAF / tetrahydrofuran / 1 h / 20 °C

9.1: 89 percent / DBU / CH₂Cl₂ / 48 h / Heating

With 1H-imidazole; dmap; borane-THF; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; silica gel; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; diisopinocampheylborane; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; toluene; acetonitrile; 1.1: Addition / 1.2: Oxidation / 2.1: Oxidation / 3.1: Rearrangement / 4.1: Substitution / 5.1: Reduction / 6.1: Substitution / 7.1: Addition / 7.2: Hydrolysis / 8.1: Substitution / 9.1: Epimerization;

DOI:10.1002/(SICI)1521-3765(20000915)6:18<3313::AID-CHEM3313>3.0.CO;2-0

Reference yield:

trans-2,4-dimethyl-8-oxabicyclo<3.2.1>oct-6-en-3-one (37081-60-0) → 1-[(2R,3R,4S,5S,6R)-4-Benzyloxy-6-(2-hydroxy-ethyl)-3,5-dimethyl-tetrahydro-pyran-2-yl]-ethanone (308350-54-1)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 89 percent / DIBAH / tetrahydrofuran / 11 h / -78 °C

2.1: NaH / tetrahydrofuran

2.2: 99 percent / tetrahydrofuran / 16 h / Heating

3.1: (-)-(Ipc)2BH / tetrahydrofuran / 336 h / -15 °C

3.2: 98 percent / H₂O₂; NaOH / tetrahydrofuran / 3 h

4.1: 96 percent / PCC; SiO₂ / CH₂Cl₂ / 15 h / 20 °C

5.1: m-CPBA; NaHCO₃ / CH₂Cl₂ / 15 h / 20 °C

6.1: 100 percent / TMSOTf / acetonitrile / -40 - -20 °C

7.1: 94 percent / BH₃*THF / CH₂Cl₂ / 3 h / 0 °C

8.1: 100 percent / imidazole; DMAP / CH₂Cl₂ / 15 h / 20 °C

9.1: toluene / 15 h / 20 °C / ultrasound

9.2: 76 percent / aq. HCl / toluene / 0.5 h

10.1: 97 percent / TBAF / tetrahydrofuran / 1 h / 20 °C

11.1: 89 percent / DBU / CH₂Cl₂ / 48 h / Heating

With 1H-imidazole; dmap; borane-THF; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; silica gel; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; diisopinocampheylborane; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; toluene; acetonitrile; 1.1: Reduction / 2.1: Metallation / 2.2: Etherification / 3.1: Addition / 3.2: Oxidation / 4.1: Oxidation / 5.1: Rearrangement / 6.1: Substitution / 7.1: Reduction / 8.1: Substitution / 9.1: Addition / 9.2: Hydrolysis / 10.1: Substitution / 11.1: Epimerization;

DOI:10.1002/(SICI)1521-3765(20000915)6:18<3313::AID-CHEM3313>3.0.CO;2-0

upstream raw materials:

1-[(2S,3R,4S,5S,6R)-4-Benzyloxy-6-(2-hydroxy-ethyl)-3,5-dimethyl-tetrahydro-pyran-2-yl]-ethanone

trans-2,4-dimethyl-8-oxabicyclo<3.2.1>oct-6-en-3-one

(1S,5R,6R,7R,8S)-7-benzyloxy-6,8-dimethyl-2,9-dioxabicyclo<3.3.1>nonan-3-one

(2S,3R,4S,5S,6R)-4-Benzyloxy-6-(2-hydroxy-ethyl)-3,5-dimethyl-tetrahydro-pyran-2-carbonitrile

Downstream raw materials:

((2R,3S,4S,5R,6R)-6-Acetyl-4-benzyloxy-3,5-dimethyl-tetrahydro-pyran-2-yl)-acetaldehyde

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