(2R^*,3S^*,4R^*,5R^*)-6-benzyloxy-4,5-epoxy-3-methyl-2-(2-tetrahydropyranyloxy)hexyl pivalate

Base Information

• Chemical Name: (2R^*,3S^*,4R^*,5R^*)-6-benzyloxy-4,5-epoxy-3-methyl-2-(2-tetrahydropyranyloxy)hexyl pivalate
• CAS No.: 143661-36-3
• Molecular Formula: C₂₄H₃₆O₆
• Molecular Weight: 420.546

Synonyms:(2R^*,3S^*,4R^*,5R^*)-6-benzyloxy-4,5-epoxy-3-methyl-2-(2-tetrahydropyranyloxy)hexyl pivalate

Chemical Property of (2R^*,3S^*,4R^*,5R^*)-6-benzyloxy-4,5-epoxy-3-methyl-2-(2-tetrahydropyranyloxy)hexyl pivalate

Chemical Property:

Purity/Quality:

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Technology Process of (2R^*,3S^*,4R^*,5R^*)-6-benzyloxy-4,5-epoxy-3-methyl-2-(2-tetrahydropyranyloxy)hexyl pivalate

There total 12 articles about (2R^*,3S^*,4R^*,5R^*)-6-benzyloxy-4,5-epoxy-3-methyl-2-(2-tetrahydropyranyloxy)hexyl pivalate 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: 99.0%

pivaloyl chloride (3282-30-2) + (2R*,3S*,4R*,5R*)-6-benzyloxy-4,5-epoxy-3-methyl-2-(2-tetrahydropyranyloxy)-1-hexanol (137532-04-8,143729-25-3) → (2R*,3S*,4R*,5R*)-6-benzyloxy-4,5-epoxy-3-methyl-2-(2-tetrahydropyranyloxy)hexyl pivalate (143661-36-3)

Guidance literature:

With dmap; In dichloromethane; for 12h; Ambient temperature;

DOI:10.1246/bcsj.65.1841

Reference yield:

3,4-dihydro-2H-pyran (110-87-2) → (2R*,3S*,4R*,5R*)-6-benzyloxy-4,5-epoxy-3-methyl-2-(2-tetrahydropyranyloxy)hexyl pivalate (143661-36-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 99 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 6 h / Ambient temperature

2: 85 percent / lithium aluminum hydride / tetrahydrofuran / 1 h / -78 °C

3: 99 percent / 4-dimethylaminopyridine / CH₂Cl₂ / 12 h / Ambient temperature

With dmap; lithium aluminium tetrahydride; pyridinium p-toluenesulfonate; In tetrahydrofuran; dichloromethane;

DOI:10.1246/bcsj.65.1841

Reference yield:

isoprpyl (2R*,3S*,4E)-6-benzyloxy-2-hydroxy-3-methyl-4-hexenoate (120506-06-1,120575-89-5,120575-90-8,120575-91-9,120575-92-0,121570-18-1,143729-26-4,143729-27-5,143729-28-6) → (2R*,3S*,4R*,5R*)-6-benzyloxy-4,5-epoxy-3-methyl-2-(2-tetrahydropyranyloxy)hexyl pivalate (143661-36-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) 1 M aq. KOH, 2.) iodine / 1.) methanol, RT, 1 d, 2.) acetonitrile, 0 deg C, 18 h

2: 90 percent / Na₂CO₃ / 48 h / Ambient temperature

3: 99 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 6 h / Ambient temperature

4: 85 percent / lithium aluminum hydride / tetrahydrofuran / 1 h / -78 °C

5: 99 percent / 4-dimethylaminopyridine / CH₂Cl₂ / 12 h / Ambient temperature

With dmap; potassium hydroxide; lithium aluminium tetrahydride; iodine; pyridinium p-toluenesulfonate; sodium carbonate; In tetrahydrofuran; dichloromethane;

DOI:10.1246/bcsj.65.1841

upstream raw materials:

pivaloyl chloride

(2S,3S)-3-((2S,3R)-3-Benzyloxymethyl-oxiranyl)-2-(tetrahydro-pyran-2-yloxy)-butan-1-ol

3,4-dihydro-2H-pyran

isopropyl (2S,3R,4E)-6-benzyloxy-2-hydroxy-3-methyl-4-hexenoate

Downstream raw materials:

ethyl (4RS^*,5R^*,6S^*,7S^*,2E)-7,9-isopropylidenedioxy-4-(p-methoxybenzyloxy)-2,6,8-trimethyl-5-(2-tetrahydropyranyloxy)-2-nonenoate

ethyl (4RS^*,5R^*,6S^*,7S^*,2Z)-7,9-isopropylidenedioxy-4-(p-methoxybenzyloxy)-2,6,8-trimethyl-5-(2-tetrahydropyranyloxy)-2-nonenoate

(Z)-(5S,6R)-4-(4-Methoxy-benzyloxy)-2-methyl-5-(tetrahydro-pyran-2-yloxy)-6-((4R,5R)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-hept-2-enoic acid

(5RS^*,6R^*,7S^*,8S^*,9S^*,3Z)-8,10-isopropylidendioxy-5-(p-methoxybenzyloxy)-3,7,9-trimethyl-6-(2-tetrahydropyranyloxy)-3-decen-2-one

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