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

Base Information

• Chemical Name: methyl (2R^*,3S^*,4R^*,5R^*)-6-benzyloxy-4,5-epoxy-3-methyl-2-(2-tetrahydropyranyloxy)hexanoate
• CAS No.: 143661-35-2
• Molecular Formula: C₂₀H₂₈O₆
• Molecular Weight: 364.439
• Mol file: 143661-35-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 5 articles about methyl (2R^*,3S^*,4R^*,5R^*)-6-benzyloxy-4,5-epoxy-3-methyl-2-(2-tetrahydropyranyloxy)hexanoate 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%

3,4-dihydro-2H-pyran (110-87-2) + methyl(2R*,3R*,4R*,5R*)-6-benzyloxy-4,5-epoxy-2-hydroxy-3-methylhexanoate (121485-05-0) → methyl (2R*,3S*,4R*,5R*)-6-benzyloxy-4,5-epoxy-3-methyl-2-(2-tetrahydropyranyloxy)hexanoate (143661-35-2)

Guidance literature:

With pyridinium p-toluenesulfonate; In dichloromethane; for 6h; Ambient temperature;

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) → methyl (2R*,3S*,4R*,5R*)-6-benzyloxy-4,5-epoxy-3-methyl-2-(2-tetrahydropyranyloxy)hexanoate (143661-35-2)

Guidance literature:

Multi-step reaction with 3 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

With potassium hydroxide; iodine; pyridinium p-toluenesulfonate; sodium carbonate; In dichloromethane;

DOI:10.1246/bcsj.65.1841

Reference yield:

(2R*,3R*,4R*,5S*)-6-benzyloxy-2-hydroxy-5-iodo-3-methyl-4-hexanolide (137532-03-7,143729-24-2) → methyl (2R*,3S*,4R*,5R*)-6-benzyloxy-4,5-epoxy-3-methyl-2-(2-tetrahydropyranyloxy)hexanoate (143661-35-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / Na₂CO₃ / 48 h / Ambient temperature

2: 99 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 6 h / Ambient temperature

With pyridinium p-toluenesulfonate; sodium carbonate; In dichloromethane;

DOI:10.1246/bcsj.65.1841

upstream raw materials:

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

3,4-dihydro-2H-pyran

methyl(2R^*,3R^*,4R^*,5R^*)-6-benzyloxy-4,5-epoxy-2-hydroxy-3-methylhexanoate

isoprpyl (2R^*,3S^*,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