(3S,4R,4aS,6S,7aS)-4a-(2-Hydroxy-2-methyl-propyl)-3-methoxy-4-[3-(4-methoxy-phenoxy)-propyl]-octahydro-cyclopenta[c]pyran-6-ol

Base Information

• Chemical Name: (3S,4R,4aS,6S,7aS)-4a-(2-Hydroxy-2-methyl-propyl)-3-methoxy-4-[3-(4-methoxy-phenoxy)-propyl]-octahydro-cyclopenta[c]pyran-6-ol
• CAS No.: 194734-27-5
• Molecular Formula: C₂₃H₃₆O₆
• Molecular Weight: 408.535
• Mol file: 194734-27-5.mol

Synonyms:

Chemical Property of (3S,4R,4aS,6S,7aS)-4a-(2-Hydroxy-2-methyl-propyl)-3-methoxy-4-[3-(4-methoxy-phenoxy)-propyl]-octahydro-cyclopenta[c]pyran-6-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4R,4aS,6S,7aS)-4a-(2-Hydroxy-2-methyl-propyl)-3-methoxy-4-[3-(4-methoxy-phenoxy)-propyl]-octahydro-cyclopenta[c]pyran-6-ol

There total 22 articles about (3S,4R,4aS,6S,7aS)-4a-(2-Hydroxy-2-methyl-propyl)-3-methoxy-4-[3-(4-methoxy-phenoxy)-propyl]-octahydro-cyclopenta[c]pyran-6-ol 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%

methyllithium (917-54-4) + Benzoic acid (3S,4R,4aS,6S,7aS)-3-methoxy-4a-methoxycarbonylmethyl-4-[3-(4-methoxy-phenoxy)-propyl]-octahydro-cyclopenta[c]pyran-6-yl ester (194734-26-4) → (3S,4R,4aS,6S,7aS)-4a-(2-Hydroxy-2-methyl-propyl)-3-methoxy-4-[3-(4-methoxy-phenoxy)-propyl]-octahydro-cyclopenta[c]pyran-6-ol (194734-27-5)

Guidance literature:

In diethyl ether; -78 deg C to rt;

DOI:10.1016/S0040-4039(97)01347-6

Reference yield:

4-methoxy-phenol (150-76-5) → (3S,4R,4aS,6S,7aS)-4a-(2-Hydroxy-2-methyl-propyl)-3-methoxy-4-[3-(4-methoxy-phenoxy)-propyl]-octahydro-cyclopenta[c]pyran-6-ol (194734-27-5)

Guidance literature:

Multi-step reaction with 20 steps

1: DEAD, Ph₃P / CH₂Cl₂ / Ambient temperature

2: H₂ / Pd(C) / methanol

3: 1.) MsCl, Et₃N, 2.) NaOMe / 1.) CH₂Cl₂, -10 deg C, 2.) MeOH

4: 95 percent / diethyl ether / Ambient temperature

5: Dowex-50(H+)

6: pyridine / Ambient temperature

7: 1.) NMO, OsO₄, 2.) H₅IO₆ / 1.) t-BuOH, H₂O

8: tetrahydrofuran / -78 °C

9: 76 percent / Dess-Martin periodinane / CH₂Cl₂; acetonitrile; H₂O / 1 h

10: 59 percent / LiCl, i-Pr₂NEt, 4 Angstroem molecular sieves / acetonitrile / 60 °C

11: 69 percent / BF₃*OEt₂ / tetrahydrofuran / -78 - -40 °C

12: 1.) KBHEt₃, 2.) Et₃N, DMAP, 3.) BH₃, H₂O₂, NaHCO₃ / 1.) THF, -78 deg C, 2.) CH₂Cl₂, rt, 3.) THF, rt

13: 1.) NMO, TPAP, 4 Angstroem molecular sieves, 2.) KMnO₄ / 1.) CH₃CN, 2.) t-BuOH, aq. NaH₂PO₄

15: Bu₄NF / tetrahydrofuran

16: 1.) NMO, TPAP, 4 Angstroem molecular sieves, 2.) KMnO₄ / 1.) CH₃CN, 2.) t-BuOH, aq. NaH₂PO₄

17: (COCl)2, DMF / benzene

18: DMAP

19: Bu₃SnH, AIBN / Heating

20: 95 percent / diethyl ether / -78 deg C to rt

With dmap; potassium permanganate; osmium(VIII) oxide; N-methyl-2-indolinone; tetrapropylammonium perruthennate; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); 4 A molecular sieve; DOWEX-50(H+); boron trifluoride diethyl etherate; borane; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; tri-n-butyl-tin hydride; sodium methylate; potassium triethylborohydride; sodium hydrogencarbonate; Dess-Martin periodane; methanesulfonyl chloride; periodic acid; triethylamine; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; triphenylphosphine; lithium chloride; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; diethyl ether; dichloromethane; water; acetonitrile; benzene;

DOI:10.1016/S0040-4039(97)01347-6

Reference yield:

Acetic acid (1R,2S,3R,4R,5R)-4-allyl-2-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-3-yl ester (157116-97-7) → (3S,4R,4aS,6S,7aS)-4a-(2-Hydroxy-2-methyl-propyl)-3-methoxy-4-[3-(4-methoxy-phenoxy)-propyl]-octahydro-cyclopenta[c]pyran-6-ol (194734-27-5)

Guidance literature:

Multi-step reaction with 21 steps

1: 1.) Cy₂BH, 2.) H₂O₂, NaHCO₃ / 1.) THF

2: DEAD, Ph₃P / CH₂Cl₂ / Ambient temperature

3: H₂ / Pd(C) / methanol

4: 1.) MsCl, Et₃N, 2.) NaOMe / 1.) CH₂Cl₂, -10 deg C, 2.) MeOH

5: 95 percent / diethyl ether / Ambient temperature

6: Dowex-50(H+)

7: pyridine / Ambient temperature

8: 1.) NMO, OsO₄, 2.) H₅IO₆ / 1.) t-BuOH, H₂O

9: tetrahydrofuran / -78 °C

10: 76 percent / Dess-Martin periodinane / CH₂Cl₂; acetonitrile; H₂O / 1 h

11: 59 percent / LiCl, i-Pr₂NEt, 4 Angstroem molecular sieves / acetonitrile / 60 °C

12: 69 percent / BF₃*OEt₂ / tetrahydrofuran / -78 - -40 °C

13: 1.) KBHEt₃, 2.) Et₃N, DMAP, 3.) BH₃, H₂O₂, NaHCO₃ / 1.) THF, -78 deg C, 2.) CH₂Cl₂, rt, 3.) THF, rt

14: 1.) NMO, TPAP, 4 Angstroem molecular sieves, 2.) KMnO₄ / 1.) CH₃CN, 2.) t-BuOH, aq. NaH₂PO₄

16: Bu₄NF / tetrahydrofuran

17: 1.) NMO, TPAP, 4 Angstroem molecular sieves, 2.) KMnO₄ / 1.) CH₃CN, 2.) t-BuOH, aq. NaH₂PO₄

18: (COCl)2, DMF / benzene

19: DMAP

20: Bu₃SnH, AIBN / Heating

21: 95 percent / diethyl ether / -78 deg C to rt

With dmap; potassium permanganate; osmium(VIII) oxide; N-methyl-2-indolinone; tetrapropylammonium perruthennate; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); 4 A molecular sieve; DOWEX-50(H+); boron trifluoride diethyl etherate; bis(cyclohexanyl)borane; borane; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; tri-n-butyl-tin hydride; sodium methylate; potassium triethylborohydride; sodium hydrogencarbonate; Dess-Martin periodane; methanesulfonyl chloride; periodic acid; triethylamine; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; triphenylphosphine; lithium chloride; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; diethyl ether; dichloromethane; water; acetonitrile; benzene;

DOI:10.1016/S0040-4039(97)01347-6

upstream raw materials:

methyllithium

Benzoic acid (3S,4R,4aS,6S,7aS)-3-methoxy-4a-methoxycarbonylmethyl-4-[3-(4-methoxy-phenoxy)-propyl]-octahydro-cyclopenta[c]pyran-6-yl ester

4-methoxy-phenol

Acetic acid (1R,2S,3R,4R,5R)-4-allyl-2-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-3-yl ester