Thiocarbonic acid O-[(2R,3S,4R,5R,6R)-2-methoxy-3,5-dimethyl-6-((S)-1-methyl-butyl)-tetrahydro-pyran-4-yl] ester O-phenyl ester

Base Information

• Chemical Name: Thiocarbonic acid O-[(2R,3S,4R,5R,6R)-2-methoxy-3,5-dimethyl-6-((S)-1-methyl-butyl)-tetrahydro-pyran-4-yl] ester O-phenyl ester
• CAS No.: 115047-21-7
• Molecular Formula: C₂₀H₃₀O₄S
• Molecular Weight: 366.522

Synonyms:Thiocarbonic acid O-[(2R,3S,4R,5R,6R)-2-methoxy-3,5-dimethyl-6-((S)-1-methyl-butyl)-tetrahydro-pyran-4-yl] ester O-phenyl ester

Chemical Property of Thiocarbonic acid O-[(2R,3S,4R,5R,6R)-2-methoxy-3,5-dimethyl-6-((S)-1-methyl-butyl)-tetrahydro-pyran-4-yl] ester O-phenyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of Thiocarbonic acid O-[(2R,3S,4R,5R,6R)-2-methoxy-3,5-dimethyl-6-((S)-1-methyl-butyl)-tetrahydro-pyran-4-yl] ester O-phenyl ester

There total 16 articles about Thiocarbonic acid O-[(2R,3S,4R,5R,6R)-2-methoxy-3,5-dimethyl-6-((S)-1-methyl-butyl)-tetrahydro-pyran-4-yl] ester O-phenyl ester 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:

4(R)-(1(S)-methyl-2(E)-heptenyl)-2,2,5(S)-trimethyl-1,3-dioxane (104784-08-9) → Thiocarbonic acid O-[(2R,3S,4R,5R,6R)-2-methoxy-3,5-dimethyl-6-((S)-1-methyl-butyl)-tetrahydro-pyran-4-yl] ester O-phenyl ester (115047-21-7)

Guidance literature:

Multi-step reaction with 15 steps

1: 1.) ozone, 2.) dimethyl sulfide / 1.) methanol, -78 deg C, 2.) methanol, 25 deg C, 18 h

2: 1.35 g / diethyl ether / 20 h / 25 °C

3: 83 percent / hydrogen / Raney nickel W-2 / diethyl ether / 48 h / 25 °C

4: 100 percent / HCl / tetrahydrofuran; H₂O / Heating

5: 93 percent / pyridine / 18 h / -6 °C

6: 180 mg / dimethylsulfoxide / 24 h / 80 °C

7: 78 percent / HCl / methanol; H₂O / 24 h / Heating

8: 1.) LDA / 1.) THF, hexane, -78 deg C

9: 1.) NaH, 2.) (Ph₃P)4Pd, Ph₃P / 1.) THF, 25 deg C, 2.) THF, 25 deg C, 3 h

10: 69 percent / LiCl / dimethylsulfoxide; H₂O / 19 h / 150 °C

11: diethyl ether / 15 h / -18 °C

12: H₂O₂, HOAc / tetrahydrofuran / 0 deg C, 30 min, 25 deg C, 16 h

13: 1.)triethylamine, 4-(dimethylamino)pyridine, acetic anhydride, 2.) LiAlH₄ / 1.) CH₂Cl₂, 0 deg C, 30 min, 25 deg C, 1 h, reflux, 6 h, 2.) ether, 0 deg C, 1 h, 25 deg C, 16 h

15: 1.) n-BuLi / 1.) THF, -18 deg C, 1 h, 2.) THF, from -18 deg C up to 25 deg C

With pyridine; hydrogenchloride; dmap; lithium aluminium tetrahydride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; dimethylsulfide; hydrogen; dihydrogen peroxide; acetic anhydride; sodium hydride; ozone; acetic acid; triethylamine; triphenylphosphine; lithium chloride; lithium diisopropyl amide; Raney nickel W-2; In tetrahydrofuran; methanol; diethyl ether; water; dimethyl sulfoxide;

DOI:10.1021/ja00224a032

Reference yield:

(4R,5S)-2,2,5-Trimethyl-4-((E)-(S)-1-methyl-but-2-enyl)-[1,3]dioxane (104784-10-3,104871-10-5) → Thiocarbonic acid O-[(2R,3S,4R,5R,6R)-2-methoxy-3,5-dimethyl-6-((S)-1-methyl-butyl)-tetrahydro-pyran-4-yl] ester O-phenyl ester (115047-21-7)

Guidance literature:

Multi-step reaction with 13 steps

1: 83 percent / hydrogen / Raney nickel W-2 / diethyl ether / 48 h / 25 °C

2: 100 percent / HCl / tetrahydrofuran; H₂O / Heating

3: 93 percent / pyridine / 18 h / -6 °C

4: 180 mg / dimethylsulfoxide / 24 h / 80 °C

5: 78 percent / HCl / methanol; H₂O / 24 h / Heating

6: 1.) LDA / 1.) THF, hexane, -78 deg C

7: 1.) NaH, 2.) (Ph₃P)4Pd, Ph₃P / 1.) THF, 25 deg C, 2.) THF, 25 deg C, 3 h

8: 69 percent / LiCl / dimethylsulfoxide; H₂O / 19 h / 150 °C

9: diethyl ether / 15 h / -18 °C

10: H₂O₂, HOAc / tetrahydrofuran / 0 deg C, 30 min, 25 deg C, 16 h

11: 1.)triethylamine, 4-(dimethylamino)pyridine, acetic anhydride, 2.) LiAlH₄ / 1.) CH₂Cl₂, 0 deg C, 30 min, 25 deg C, 1 h, reflux, 6 h, 2.) ether, 0 deg C, 1 h, 25 deg C, 16 h

13: 1.) n-BuLi / 1.) THF, -18 deg C, 1 h, 2.) THF, from -18 deg C up to 25 deg C

With pyridine; hydrogenchloride; dmap; lithium aluminium tetrahydride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; hydrogen; dihydrogen peroxide; acetic anhydride; sodium hydride; acetic acid; triethylamine; triphenylphosphine; lithium chloride; lithium diisopropyl amide; Raney nickel W-2; In tetrahydrofuran; methanol; diethyl ether; water; dimethyl sulfoxide;

DOI:10.1021/ja00224a032

Reference yield:

(2R,3S,4S)-3,5-isopropylidenedioxy-2,4-dimethylpentanal (110715-70-3) → Thiocarbonic acid O-[(2R,3S,4R,5R,6R)-2-methoxy-3,5-dimethyl-6-((S)-1-methyl-butyl)-tetrahydro-pyran-4-yl] ester O-phenyl ester (115047-21-7)

Guidance literature:

Multi-step reaction with 14 steps

1: 1.35 g / diethyl ether / 20 h / 25 °C

2: 83 percent / hydrogen / Raney nickel W-2 / diethyl ether / 48 h / 25 °C

3: 100 percent / HCl / tetrahydrofuran; H₂O / Heating

4: 93 percent / pyridine / 18 h / -6 °C

5: 180 mg / dimethylsulfoxide / 24 h / 80 °C

6: 78 percent / HCl / methanol; H₂O / 24 h / Heating

7: 1.) LDA / 1.) THF, hexane, -78 deg C

8: 1.) NaH, 2.) (Ph₃P)4Pd, Ph₃P / 1.) THF, 25 deg C, 2.) THF, 25 deg C, 3 h

9: 69 percent / LiCl / dimethylsulfoxide; H₂O / 19 h / 150 °C

10: diethyl ether / 15 h / -18 °C

11: H₂O₂, HOAc / tetrahydrofuran / 0 deg C, 30 min, 25 deg C, 16 h

12: 1.)triethylamine, 4-(dimethylamino)pyridine, acetic anhydride, 2.) LiAlH₄ / 1.) CH₂Cl₂, 0 deg C, 30 min, 25 deg C, 1 h, reflux, 6 h, 2.) ether, 0 deg C, 1 h, 25 deg C, 16 h

14: 1.) n-BuLi / 1.) THF, -18 deg C, 1 h, 2.) THF, from -18 deg C up to 25 deg C

With pyridine; hydrogenchloride; dmap; lithium aluminium tetrahydride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; hydrogen; dihydrogen peroxide; acetic anhydride; sodium hydride; acetic acid; triethylamine; triphenylphosphine; lithium chloride; lithium diisopropyl amide; Raney nickel W-2; In tetrahydrofuran; methanol; diethyl ether; water; dimethyl sulfoxide;

DOI:10.1021/ja00224a032

upstream raw materials:

3(S),5(S)-dimethyl-3(S)-hydroxy-6(R)-(1(S)-methylbutyl)-2(R)-methoxytetrahydro-2H-pyran

phenylcarbonochloridothioate

2(S),4(S)-dimethylheptane-1,3(R)-diol

4(R)-(1(S)-methylbutyl)-2,2,5(S)-trimethyl-1,3-dioxane

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