(+/-)-isocelorbicol

Base Information

• Chemical Name: (+/-)-isocelorbicol
• CAS No.: 88764-00-5
• Molecular Formula: C₁₅H₂₆O₄
• Molecular Weight: 270.369
• Mol file: 88764-00-5.mol

Synonyms:

Chemical Property of (+/-)-isocelorbicol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-isocelorbicol

There total 16 articles about (+/-)-isocelorbicol 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: 95.0%

C18H30O3 → (+/-)-isocelorbicol (59812-47-4,88764-00-5,88764-05-0)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; at 25 ℃; for 1h;

DOI:10.1016/S0040-4020(01)87737-1

Reference yield:

2,3-dehydro-4α-methyl-9β-hydroxydihydroagarofuran (117212-74-5) → (+/-)-isocelorbicol (59812-47-4,88764-00-5,88764-05-0)

Guidance literature:

Multi-step reaction with 11 steps

1: 1.) 2,2'-bipyridyl, 1.6M n-butyllithium / 1.) THF, hexane, 10 min, 2.) THF, RT, 15 min then 1h, reflux

2: 60 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 4 h / 25 °C

3: 56 percent / NaBH₄ / ethanol / 1.5 h / Heating

4: 87 percent / diisopropylamine, 85percent m-chloroperbenzoic acid / CH₂Cl₂ / 1 h / -78 °C

5: 1.) osmium tetraoxide, 2.) sodium bisulfite, H₂O, pyridine / 1.) pyridine, 20h, RT, 2.) 3h

6: 87 percent / (+)-10-camphorsulfonic acid / cyclopentane / 3 h / 50 °C

7: 1.) 60percent NaH, imidazole / 1.) THF, oil, 2h, 60 deg C, 2.) 1h, 50 deg C

8: 86 percent / 0.5 h / Ambient temperature

9: 95 percent / tri-n-butyltin hydride / toluene / 1.) 20h, reflux, 2.) 50 deg C, 15 mmHg

10: 90 percent / 0.2M Ba(OH)2 / methanol / 6 h / Heating

11: 95 percent / 1N aq. HCl / tetrahydrofuran / 1 h / 25 °C

With pyridine; 1H-imidazole; hydrogenchloride; [2,2]bipyridinyl; barium dihydroxide; sodium tetrahydroborate; osmium(VIII) oxide; n-butyllithium; water; tri-n-butyl-tin hydride; sodium hydride; sodium hydrogensulfite; (+)-10-camphorsulfonic acid; diisopropylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; ethanol; dichloromethane; Cyclopentane; toluene;

DOI:10.1016/S0040-4020(01)87737-1

Reference yield:

2,3-dehydro-4α-methyl-9-ketodihydroagarofuran (102342-22-3) → (+/-)-isocelorbicol (59812-47-4,88764-00-5,88764-05-0)

Guidance literature:

Multi-step reaction with 12 steps

1: 98 percent / LiAlH₄ / diethyl ether / 1.) -50 deg C, 5h, 2.) RT, 18h

2: 1.) 2,2'-bipyridyl, 1.6M n-butyllithium / 1.) THF, hexane, 10 min, 2.) THF, RT, 15 min then 1h, reflux

3: 60 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 4 h / 25 °C

4: 56 percent / NaBH₄ / ethanol / 1.5 h / Heating

5: 87 percent / diisopropylamine, 85percent m-chloroperbenzoic acid / CH₂Cl₂ / 1 h / -78 °C

6: 1.) osmium tetraoxide, 2.) sodium bisulfite, H₂O, pyridine / 1.) pyridine, 20h, RT, 2.) 3h

7: 87 percent / (+)-10-camphorsulfonic acid / cyclopentane / 3 h / 50 °C

8: 1.) 60percent NaH, imidazole / 1.) THF, oil, 2h, 60 deg C, 2.) 1h, 50 deg C

9: 86 percent / 0.5 h / Ambient temperature

10: 95 percent / tri-n-butyltin hydride / toluene / 1.) 20h, reflux, 2.) 50 deg C, 15 mmHg

11: 90 percent / 0.2M Ba(OH)2 / methanol / 6 h / Heating

12: 95 percent / 1N aq. HCl / tetrahydrofuran / 1 h / 25 °C

With pyridine; 1H-imidazole; hydrogenchloride; [2,2]bipyridinyl; barium dihydroxide; sodium tetrahydroborate; osmium(VIII) oxide; lithium aluminium tetrahydride; n-butyllithium; water; tri-n-butyl-tin hydride; sodium hydride; sodium hydrogensulfite; (+)-10-camphorsulfonic acid; diisopropylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; Cyclopentane; toluene;

DOI:10.1016/S0040-4020(01)87737-1

upstream raw materials:

2,3-dehydro-4α-methyl-9β-hydroxydihydroagarofuran

2,3-dehydro-4α-methyl-9-ketodihydroagarofuran

3β-hydroxy-4α-methyl-9-ketodihydroagarofuran

9-keto-α-agarofuran