methyl (1R^*,3aR^*,4S^*,6aR^*)-2,2-dimethyl-2,3,3a,4,6,6a-hexahydro-5-oxo-4-phenylthiomethyl-1-(2-tetrahydropyranyloxy)ethyl-3a(1H)pentaleneacetate

Base Information

• Chemical Name: methyl (1R^*,3aR^*,4S^*,6aR^*)-2,2-dimethyl-2,3,3a,4,6,6a-hexahydro-5-oxo-4-phenylthiomethyl-1-(2-tetrahydropyranyloxy)ethyl-3a(1H)pentaleneacetate
• CAS No.: 97330-28-4
• Molecular Formula: C₂₇H₃₈O₅S
• Molecular Weight: 474.662

Synonyms:methyl (1R^*,3aR^*,4S^*,6aR^*)-2,2-dimethyl-2,3,3a,4,6,6a-hexahydro-5-oxo-4-phenylthiomethyl-1-(2-tetrahydropyranyloxy)ethyl-3a(1H)pentaleneacetate

Chemical Property of methyl (1R^*,3aR^*,4S^*,6aR^*)-2,2-dimethyl-2,3,3a,4,6,6a-hexahydro-5-oxo-4-phenylthiomethyl-1-(2-tetrahydropyranyloxy)ethyl-3a(1H)pentaleneacetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (1R^*,3aR^*,4S^*,6aR^*)-2,2-dimethyl-2,3,3a,4,6,6a-hexahydro-5-oxo-4-phenylthiomethyl-1-(2-tetrahydropyranyloxy)ethyl-3a(1H)pentaleneacetate

There total 18 articles about methyl (1R^*,3aR^*,4S^*,6aR^*)-2,2-dimethyl-2,3,3a,4,6,6a-hexahydro-5-oxo-4-phenylthiomethyl-1-(2-tetrahydropyranyloxy)ethyl-3a(1H)pentaleneacetate 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:

3,4-dihydro-2H-pyran (110-87-2) → methyl (1R*,3aR*,4S*,6aR*)-2,2-dimethyl-2,3,3a,4,6,6a-hexahydro-5-oxo-4-phenylthiomethyl-1-(2-tetrahydropyranyloxy)ethyl-3a(1H)pentaleneacetate (97330-28-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 88 percent / p-TsOH / CH₂Cl₂ / 0.67 h / 0 °C

2: 68 percent / sodium hydride / benzene; 2-methyl-butan-2-ol / 2.5 h / Heating

3: 63 percent / benzene / 12 h / 45 °C

4: 42 mg / KOH / H₂O; ethane-1,2-diol / 1.5 h / Heating

5: 1.) lithium / 1.) liq. NH₃, THF, tert-BuOH, 2 min; 2.) THF, up to r.t.

With potassium hydroxide; lithium; sodium hydride; toluene-4-sulfonic acid; In tert-Amyl alcohol; dichloromethane; water; ethylene glycol; benzene;

Reference yield:

(2R*,3R*)-2-acetonyl-4,4-dimethyl-3-(2-hydroxyethyl)cyclopentan-1-one (97330-23-9) → methyl (1R*,3aR*,4S*,6aR*)-2,2-dimethyl-2,3,3a,4,6,6a-hexahydro-5-oxo-4-phenylthiomethyl-1-(2-tetrahydropyranyloxy)ethyl-3a(1H)pentaleneacetate (97330-28-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 88 percent / p-TsOH / CH₂Cl₂ / 0.67 h / 0 °C

2: 68 percent / sodium hydride / benzene; 2-methyl-butan-2-ol / 2.5 h / Heating

3: 63 percent / benzene / 12 h / 45 °C

4: 42 mg / KOH / H₂O; ethane-1,2-diol / 1.5 h / Heating

5: 1.) lithium / 1.) liq. NH₃, THF, tert-BuOH, 2 min; 2.) THF, up to r.t.

With potassium hydroxide; lithium; sodium hydride; toluene-4-sulfonic acid; In tert-Amyl alcohol; dichloromethane; water; ethylene glycol; benzene;

Reference yield:

2-allyl-4,4-dimehtylcyclopent-2-en-1-one (97330-15-9) → methyl (1R*,3aR*,4S*,6aR*)-2,2-dimethyl-2,3,3a,4,6,6a-hexahydro-5-oxo-4-phenylthiomethyl-1-(2-tetrahydropyranyloxy)ethyl-3a(1H)pentaleneacetate (97330-28-4)

Guidance literature:

Multi-step reaction with 11 steps

1: 65 percent / oxygen, PdCl₂, CuCl / dimethylformamide; H₂O / 12 h

2: 80 percent / p-TsOH / benzene / 2.5 h / Heating

3: 1.) Mg, I₂; 2.) CuI*(n-Bu)3P / 1.) THF, reflux, 1 h; 2.) THF, 2 h, - 78 deg C

4: 75 percent / p-TsOH / benzene / 2.5 h / Heating

5: 70 percent / diborane, 3 N NaOH, 30percent H₂O₂ / tetrahydrofuran / 1 h / 40 °C

6: 60 percent / 1 N hydrochloric acid / tetrahydrofuran / 2 h / Ambient temperature

7: 88 percent / p-TsOH / CH₂Cl₂ / 0.67 h / 0 °C

8: 68 percent / sodium hydride / benzene; 2-methyl-butan-2-ol / 2.5 h / Heating

9: 63 percent / benzene / 12 h / 45 °C

10: 42 mg / KOH / H₂O; ethane-1,2-diol / 1.5 h / Heating

11: 1.) lithium / 1.) liq. NH₃, THF, tert-BuOH, 2 min; 2.) THF, up to r.t.

With hydrogenchloride; potassium hydroxide; sodium hydroxide; CuI*P(n-Bu)3; dihydrogen peroxide; iodine; oxygen; lithium; sodium hydride; toluene-4-sulfonic acid; magnesium; copper(l) chloride; palladium dichloride; diborane; In tetrahydrofuran; tert-Amyl alcohol; dichloromethane; water; ethylene glycol; N,N-dimethyl-formamide; benzene;

upstream raw materials:

diazomethane

iodomethyl phenyl sulfide

3,4-dihydro-2H-pyran

2,2-dimethyl-4-oxopentenal

Downstream raw materials:

[(1R,3aR,4R,6aR)-1-(2-Hydroxy-ethyl)-2,2-dimethyl-5-oxo-4-phenylsulfanylmethyl-hexahydro-pentalen-3a-yl]-acetic acid methyl ester

methyl (1R^*,3aR^*,4S^*,6aR^*)-2,2-dimethyl-2,3,3a,4,6,6a-hexahydro-1-(2-hydroxyethyl)-5-oxo-4-phenylthiomethyl-3a(1H)-pentaleneacetate

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