(2R^*)-2-<(1S^*,4RS^*,5S^*,6R^*,7R^*)-4-(p-methoxybenzyloxy)-1,2,6-trimethyl-8,9-dioxabicyclo<3.3.1>non-2-en-7-yl>-1-propanol

Base Information

• Chemical Name: (2R^*)-2-<(1S^*,4RS^*,5S^*,6R^*,7R^*)-4-(p-methoxybenzyloxy)-1,2,6-trimethyl-8,9-dioxabicyclo<3.3.1>non-2-en-7-yl>-1-propanol
• CAS No.: 143661-44-3
• Molecular Formula: C₂₁H₃₀O₅
• Molecular Weight: 362.466
• Mol file: 143661-44-3.mol

Synonyms:

Chemical Property of (2R^*)-2-<(1S^*,4RS^*,5S^*,6R^*,7R^*)-4-(p-methoxybenzyloxy)-1,2,6-trimethyl-8,9-dioxabicyclo<3.3.1>non-2-en-7-yl>-1-propanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R^*)-2-<(1S^*,4RS^*,5S^*,6R^*,7R^*)-4-(p-methoxybenzyloxy)-1,2,6-trimethyl-8,9-dioxabicyclo<3.3.1>non-2-en-7-yl>-1-propanol

There total 16 articles about (2R^*)-2-<(1S^*,4RS^*,5S^*,6R^*,7R^*)-4-(p-methoxybenzyloxy)-1,2,6-trimethyl-8,9-dioxabicyclo<3.3.1>non-2-en-7-yl>-1-propanol 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: 57.0%

(5RS*,6R*,7S*,8S*,9S*,3Z)-8,10-isopropylidendioxy-5-(p-methoxybenzyloxy)-3,7,9-trimethyl-6-(2-tetrahydropyranyloxy)-3-decen-2-one (143661-43-2,143729-30-0) → (2R*)-2-<(1S*,4RS*,5S*,6R*,7R*)-4-(p-methoxybenzyloxy)-1,2,6-trimethyl-8,9-dioxabicyclo<3.3.1>non-2-en-7-yl>-1-propanol (143661-44-3,143729-29-7)

Guidance literature:

With pyridinium p-toluenesulfonate; In methanol; for 20h; 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) → (2R*)-2-<(1S*,4RS*,5S*,6R*,7R*)-4-(p-methoxybenzyloxy)-1,2,6-trimethyl-8,9-dioxabicyclo<3.3.1>non-2-en-7-yl>-1-propanol (143661-44-3,143729-29-7)

Guidance literature:

Multi-step reaction with 17 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

6: 99 percent / H₂ / 10percent Pd/C / ethanol / 8 h

7: 1.) Me₂S complex of copper(I) iodide / 1.) ether, -30 deg C, 2.) ether, 5 deg C, 13 h

8: 89 percent / pyridinium p-toluenesulfonate / benzene / 12 h / Ambient temperature

9: 99 percent / 1 M aq. KOH / methanol / 20 h / Ambient temperature

10: 97 percent / dimethyl sulfoxide, oxalyl chloride / CH₂Cl₂ / 0.17 h / -60 °C

11: 1.) BuLi / 1.) THF, hexane, -20 deg C, 20 min, 2.) THF, hexane, a) -20 deg C, 2 h, b) 5 deg C, 40 h

12: 63 percent / NaH / tetrahydrofuran; dimethylformamide / 16 h / Ambient temperature

13: 55 percent / methyl iodide, calcium carbonate / acetonitrile; H₂O / 40 h / Ambient temperature

14: 1.) sodium hydride / 1.) ether, RT, 1 h, 2.) ether, -20 deg C, 12 h

15: 87 percent / 1 M aq. KOH / methanol / 48 h / Ambient temperature

16: 79 percent / diethyl ether / 1 h / Ambient temperature

17: 57 percent / pyridinium p-toluenesulfonate / methanol / 20 h / Ambient temperature

With dmap; potassium hydroxide; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; copper(I) iodide dimethyl sulfide complex; hydrogen; iodine; pyridinium p-toluenesulfonate; sodium hydride; sodium carbonate; dimethyl sulfoxide; calcium carbonate; methyl iodide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; benzene;

DOI:10.1246/bcsj.65.1841

Reference yield:

(2R*,3S*,4R*,5R*)-6-benzyloxy-4,5-epoxy-3-methyl-2-(2-tetrahydropyranyloxy)hexyl pivalate (143661-36-3) → (2R*)-2-<(1S*,4RS*,5S*,6R*,7R*)-4-(p-methoxybenzyloxy)-1,2,6-trimethyl-8,9-dioxabicyclo<3.3.1>non-2-en-7-yl>-1-propanol (143661-44-3,143729-29-7)

Guidance literature:

Multi-step reaction with 12 steps

1: 99 percent / H₂ / 10percent Pd/C / ethanol / 8 h

2: 1.) Me₂S complex of copper(I) iodide / 1.) ether, -30 deg C, 2.) ether, 5 deg C, 13 h

3: 89 percent / pyridinium p-toluenesulfonate / benzene / 12 h / Ambient temperature

4: 99 percent / 1 M aq. KOH / methanol / 20 h / Ambient temperature

5: 97 percent / dimethyl sulfoxide, oxalyl chloride / CH₂Cl₂ / 0.17 h / -60 °C

6: 1.) BuLi / 1.) THF, hexane, -20 deg C, 20 min, 2.) THF, hexane, a) -20 deg C, 2 h, b) 5 deg C, 40 h

7: 63 percent / NaH / tetrahydrofuran; dimethylformamide / 16 h / Ambient temperature

8: 55 percent / methyl iodide, calcium carbonate / acetonitrile; H₂O / 40 h / Ambient temperature

9: 1.) sodium hydride / 1.) ether, RT, 1 h, 2.) ether, -20 deg C, 12 h

10: 87 percent / 1 M aq. KOH / methanol / 48 h / Ambient temperature

11: 79 percent / diethyl ether / 1 h / Ambient temperature

12: 57 percent / pyridinium p-toluenesulfonate / methanol / 20 h / Ambient temperature

With potassium hydroxide; n-butyllithium; oxalyl dichloride; copper(I) iodide dimethyl sulfide complex; hydrogen; pyridinium p-toluenesulfonate; sodium hydride; dimethyl sulfoxide; calcium carbonate; methyl iodide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; benzene;

DOI:10.1246/bcsj.65.1841

upstream raw materials:

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

isoprpyl (2R^*,3S^*,4E)-6-benzyloxy-2-hydroxy-3-methyl-4-hexenoate

(2R^*,3S^*,4S^*,5S^*)-4,6-isopropylidenedioxy-3,5-dimethyl-2-(2-tetrahydropyranyloxy)-1-hexanol

(2R^*,3R^*,4R^*,5S^*)-6-benzyloxy-2-hydroxy-5-iodo-3-methyl-4-hexanolide