(2S,6R)-2,6-dimethyl-8-<(2'-methoxyethoxy)methoxy>-1-(phenylthio)octane

Base Information

• Chemical Name: (2S,6R)-2,6-dimethyl-8-<(2'-methoxyethoxy)methoxy>-1-(phenylthio)octane
• CAS No.: 99474-39-2
• Molecular Formula: C₂₀H₃₄O₃S
• Molecular Weight: 354.554
• Mol file: 99474-39-2.mol

Synonyms:(2S,6R)-2,6-dimethyl-8-<(2'-methoxyethoxy)methoxy>-1-(phenylthio)octane

Chemical Property of (2S,6R)-2,6-dimethyl-8-<(2'-methoxyethoxy)methoxy>-1-(phenylthio)octane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,6R)-2,6-dimethyl-8-<(2'-methoxyethoxy)methoxy>-1-(phenylthio)octane

There total 15 articles about (2S,6R)-2,6-dimethyl-8-<(2'-methoxyethoxy)methoxy>-1-(phenylthio)octane 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:

(2'R,3'S,4R,5S)-3-(3'-hydroxy-2'-methyl-1'-oxo-5'-pentenyl)-4-methyl-5-phenyl-2-oxazolidone (113489-84-2) → (2S,6R)-2,6-dimethyl-8-<(2'-methoxyethoxy)methoxy>-1-(phenylthio)octane (99474-39-2)

Guidance literature:

Multi-step reaction with 15 steps

1: 77 percent / aq. KOH / methanol / 0.75 h / 0 °C

2: 95 percent / LiAlH₄ / tetrahydrofuran / 2.5 h / Heating

3: 4-(dimethylamino)pyridine, triethylamine / CH₂Cl₂ / 5 h

4: pyridine / CH₂Cl₂ / 2 h / Ambient temperature

6: 99 percent / H₂ / PtO₂ / ethyl acetate / 3 h

7: 98 percent / LiAlH₄ / diethyl ether / 3 h / Ambient temperature

8: 96 percent / pyridine / CH₂Cl₂ / 48 h / Ambient temperature

9: 90 percent / 18-crown-6 / various solvent(s) / 36 h / Heating

10: 82 percent / diisobutylaluminum hydride / hexane; pentane / 1.) -78 deg C, 2 h, 2.) 0 deg C, 30 min

11: 96 percent / LiAlH₄ / diethyl ether / 4 h / Ambient temperature

12: 88 percent / 4-(dimethylamino)pyridine, diisopropylethylamine / CH₂Cl₂ / 16 h / Ambient temperature

13: 96 percent / 40percent aq. HF / acetonitrile / 1 h / 0 °C

14: 100 percent / pyridine / CH₂Cl₂ / 12 h / Ambient temperature

15: 1.) n-butyllithium / 1.) THF, hexane, -20 deg C, 2.) RT, 12 h

With pyridine; dmap; potassium hydroxide; lithium aluminium tetrahydride; n-butyllithium; 18-crown-6 ether; hydrogen fluoride; hydrogen; diisobutylaluminium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; platinum(IV) oxide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; ethyl acetate; acetonitrile; pentane;

DOI:10.1021/jo00244a017

Reference yield:

syn-2,3-3-hydroxy-2-methyl-pent-4-enoic acid (113564-12-8) → (2S,6R)-2,6-dimethyl-8-<(2'-methoxyethoxy)methoxy>-1-(phenylthio)octane (99474-39-2)

Guidance literature:

Multi-step reaction with 14 steps

1: 95 percent / LiAlH₄ / tetrahydrofuran / 2.5 h / Heating

2: 4-(dimethylamino)pyridine, triethylamine / CH₂Cl₂ / 5 h

3: pyridine / CH₂Cl₂ / 2 h / Ambient temperature

5: 99 percent / H₂ / PtO₂ / ethyl acetate / 3 h

6: 98 percent / LiAlH₄ / diethyl ether / 3 h / Ambient temperature

7: 96 percent / pyridine / CH₂Cl₂ / 48 h / Ambient temperature

8: 90 percent / 18-crown-6 / various solvent(s) / 36 h / Heating

9: 82 percent / diisobutylaluminum hydride / hexane; pentane / 1.) -78 deg C, 2 h, 2.) 0 deg C, 30 min

10: 96 percent / LiAlH₄ / diethyl ether / 4 h / Ambient temperature

11: 88 percent / 4-(dimethylamino)pyridine, diisopropylethylamine / CH₂Cl₂ / 16 h / Ambient temperature

12: 96 percent / 40percent aq. HF / acetonitrile / 1 h / 0 °C

13: 100 percent / pyridine / CH₂Cl₂ / 12 h / Ambient temperature

14: 1.) n-butyllithium / 1.) THF, hexane, -20 deg C, 2.) RT, 12 h

With pyridine; dmap; lithium aluminium tetrahydride; n-butyllithium; 18-crown-6 ether; hydrogen fluoride; hydrogen; diisobutylaluminium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; platinum(IV) oxide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; ethyl acetate; acetonitrile; pentane;

DOI:10.1021/jo00244a017

Reference yield:

(2S,3S)-2-methyl-4-pentene-1,3-diol (113564-18-4) → (2S,6R)-2,6-dimethyl-8-<(2'-methoxyethoxy)methoxy>-1-(phenylthio)octane (99474-39-2)

Guidance literature:

Multi-step reaction with 13 steps

1: 4-(dimethylamino)pyridine, triethylamine / CH₂Cl₂ / 5 h

2: pyridine / CH₂Cl₂ / 2 h / Ambient temperature

4: 99 percent / H₂ / PtO₂ / ethyl acetate / 3 h

5: 98 percent / LiAlH₄ / diethyl ether / 3 h / Ambient temperature

6: 96 percent / pyridine / CH₂Cl₂ / 48 h / Ambient temperature

7: 90 percent / 18-crown-6 / various solvent(s) / 36 h / Heating

8: 82 percent / diisobutylaluminum hydride / hexane; pentane / 1.) -78 deg C, 2 h, 2.) 0 deg C, 30 min

9: 96 percent / LiAlH₄ / diethyl ether / 4 h / Ambient temperature

10: 88 percent / 4-(dimethylamino)pyridine, diisopropylethylamine / CH₂Cl₂ / 16 h / Ambient temperature

11: 96 percent / 40percent aq. HF / acetonitrile / 1 h / 0 °C

12: 100 percent / pyridine / CH₂Cl₂ / 12 h / Ambient temperature

13: 1.) n-butyllithium / 1.) THF, hexane, -20 deg C, 2.) RT, 12 h

With pyridine; dmap; lithium aluminium tetrahydride; n-butyllithium; 18-crown-6 ether; hydrogen fluoride; hydrogen; diisobutylaluminium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; platinum(IV) oxide; In diethyl ether; hexane; dichloromethane; ethyl acetate; acetonitrile; pentane;

DOI:10.1021/jo00244a017

upstream raw materials:

(2S,6R)-2,6-dimethyl-8-<(2'-methoxyethoxy)methoxy>-1-octyl methanesulfonate

thiophenol

(2S,6R)-2,6-dimethyl-8-<(2'-methoxyethoxy)methoxy>-1-octanol

(3R,7S)-8-<(tert-butyldimethylsilyl)oxy>-3,7-dimethyl-1-octanol

Downstream raw materials:

(2S,6R,10S,14R)-1-<(tert-butyldimethylsilyl)oxy>-16-<(2'-methoxyethoxy)methoxy>-9-(phenylsulfonyl)-2,6,10,14-tetramethylhexadecane

(2S,6R)-2,6-dimethyl-8-<(2'-methoxyethoxy)methoxy>-1-(phenylsulfonyl)octane