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

Base Information

• Chemical Name: 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
• CAS No.: 97330-29-5
• Molecular Formula: C₂₂H₃₀O₄S
• Molecular Weight: 390.544
• Mol file: 97330-29-5.mol

Synonyms: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

Chemical Property of 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

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-1-(2-hydroxyethyl)-5-oxo-4-phenylthiomethyl-3a(1H)-pentaleneacetate

There total 31 articles about 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 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: 89.0%

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) → 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 (97330-29-5)

Guidance literature:

With toluene-4-sulfonic acid; In methanol; for 5h; Ambient temperature;

Reference yield:

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) → [(1R,3aR,4R,6aR)-1-(2-Hydroxy-ethyl)-2,2-dimethyl-5-oxo-4-phenylsulfanylmethyl-hexahydro-pentalen-3a-yl]-acetic acid methyl ester (97330-29-5)

Guidance literature:

With toluene-4-sulfonic acid; In methanol; Ambient temperature;

DOI:10.1248/cpb.33.436

Reference yield:

2,2-dimethyl-4-oxopentenal (61031-76-3) → [(1R,3aR,4R,6aR)-1-(2-Hydroxy-ethyl)-2,2-dimethyl-5-oxo-4-phenylsulfanylmethyl-hexahydro-pentalen-3a-yl]-acetic acid methyl ester (97330-29-5)

Guidance literature:

Multi-step reaction with 18 steps

1: pTsOH / benzene / Heating

2: NaH / toluene / Heating

3: 1.)DBU; 2.) NaOH ( 2N ); 3.) H₂SO₄ ( 50 percent ) / 1.) 50 deg.C, benzene; 2.) 60 deg.C; 3.) 50 deg.C

4: KOH (10percent) / tetrahydrofuran / Heating

5: PdCl₂, CuCl, O₂ / dimethylformamide; H₂O / Ambient temperature

6: p-TsOH / benzene / Heating

7: 84 percent / CuI-n-Bu₃P / tetrahydrofuran / -78 °C

8: 75 percent / pTsOH / benzene / Heating

9: BH₃ / tetrahydrofuran / 0 °C

10: H₂O₂, NaOH (6N) / 40 °C

11: HCl (1N) / tetrahydrofuran / Ambient temperature

12: p-TsOH / CH₂Cl₂ / 0 °C

13: 68 percent / NaH, t-C₅H₁₁OH / benzene / Heating

14: 72 percent / benzene / 45 °C

15: KOH / ethane-1,2-diol; H₂O / Heating

16: Li, t-BuOH / liquid ammonia; tetrahydrofuran / -78 °C

17: 1.) -78 deg.C; 2.) 0 deg.C, diethyl ether

18: p-TsOH / methanol / Ambient temperature

With hydrogenchloride; potassium hydroxide; sodium hydroxide; tert-Amyl alcohol; CuI*P(n-Bu)3; sulfuric acid; borane; dihydrogen peroxide; oxygen; lithium; sodium hydride; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; copper(l) chloride; palladium dichloride; tert-butyl alcohol; In tetrahydrofuran; methanol; dichloromethane; ammonia; water; ethylene glycol; N,N-dimethyl-formamide; toluene; benzene;

DOI:10.1248/cpb.33.436

upstream raw materials:

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

2-allyl-4,4-dimehtylcyclopent-2-en-1-one

2-acetonyl-4,4-dimethylcyclopent-2-en-1-one

(2R^*,3R^*)-2-acetonyl-4,4-dimethyl-3-(2-hydroxyethyl)cyclopentan-1-one