(4S,5S,6R,1'R,1''S,2''S,3''S)-2,2-dimethyl-5-p-methoxybenzyloxy-4-(3'-p-methoxybenzyloxy-1'-methylpropyl)-6-(1'',2''-dimethyl-3'',4''-epoxybutyl)-1,3-dioxane

Base Information

• Chemical Name: (4S,5S,6R,1'R,1''S,2''S,3''S)-2,2-dimethyl-5-p-methoxybenzyloxy-4-(3'-p-methoxybenzyloxy-1'-methylpropyl)-6-(1'',2''-dimethyl-3'',4''-epoxybutyl)-1,3-dioxane
• CAS No.: 158817-33-5
• Molecular Formula: C₃₂H₄₆O₇
• Molecular Weight: 542.713
• Mol file: 158817-33-5.mol

Synonyms:(4S,5S,6R,1'R,1''S,2''S,3''S)-2,2-dimethyl-5-p-methoxybenzyloxy-4-(3'-p-methoxybenzyloxy-1'-methylpropyl)-6-(1'',2''-dimethyl-3'',4''-epoxybutyl)-1,3-dioxane

Chemical Property of (4S,5S,6R,1'R,1''S,2''S,3''S)-2,2-dimethyl-5-p-methoxybenzyloxy-4-(3'-p-methoxybenzyloxy-1'-methylpropyl)-6-(1'',2''-dimethyl-3'',4''-epoxybutyl)-1,3-dioxane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5S,6R,1'R,1''S,2''S,3''S)-2,2-dimethyl-5-p-methoxybenzyloxy-4-(3'-p-methoxybenzyloxy-1'-methylpropyl)-6-(1'',2''-dimethyl-3'',4''-epoxybutyl)-1,3-dioxane

There total 31 articles about (4S,5S,6R,1'R,1''S,2''S,3''S)-2,2-dimethyl-5-p-methoxybenzyloxy-4-(3'-p-methoxybenzyloxy-1'-methylpropyl)-6-(1'',2''-dimethyl-3'',4''-epoxybutyl)-1,3-dioxane 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: 100.0%

(4S,5S,6R,1'R,1''S,2''S,3''S)-2,2-dimethyl-5-p-methoxybenzyloxy-4-(3'-p-methoxybenzyloxy-1'-methylpropyl)-6-[1'',2''-dimethyl-3''-hydroxy-4''-(2,4,6-triisopropylbenzenesulfonyloxy)butyl]-1,3-dioxane (201667-83-6) → (4S,5S,6R,1'R,1''S,2''S,3''S)-2,2-dimethyl-5-p-methoxybenzyloxy-4-(3'-p-methoxybenzyloxy-1'-methylpropyl)-6-(1'',2''-dimethyl-3'',4''-epoxybutyl)-1,3-dioxane (158817-33-5)

Guidance literature:

With potassium carbonate; In methanol; at 20 ℃; for 2.5h;

DOI:10.1246/cl.1994.1611

Reference yield:

(2S,3S)-3-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2-methyl-butan-1-ol (201667-73-4) → (4S,5S,6R,1'R,1''S,2''S,3''S)-2,2-dimethyl-5-p-methoxybenzyloxy-4-(3'-p-methoxybenzyloxy-1'-methylpropyl)-6-(1'',2''-dimethyl-3'',4''-epoxybutyl)-1,3-dioxane (158817-33-5)

Guidance literature:

Multi-step reaction with 15 steps

1: 1) (COCl)2, DMSO, 2) NEt₃ / 1) CH₂Cl₂, -78 deg C, 15 min, 2) CH₂Cl₂, 0 deg C, 20 min

2: 88 percent / BuLi / tetrahydrofuran; CH₂Cl₂ / 1 h / -78 °C

3: 98 percent / H₂ / Lindlar catalyst / methanol / 48 h / 760 Torr / Ambient temperature

4: 100 percent / DMAP, NEt₃ / CH₂Cl₂ / 15 h / Ambient temperature

5: 63 percent / DDQ / CH₂Cl₂; H₂O / 0.5 h / 0 °C

6: 90 percent / pyridinium dichromate, 4 Angstroem molecular sieves / CH₂Cl₂ / 2 h / Ambient temperature

7: NaClO₂, NaH₂PO₄*2H₂O, 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O / 1.5 h / 0 °C

8: 34.0 mg / KOH / methanol; H₂O / 24 h / Ambient temperature

9: 1) 2,4,6-trichlorobenzoyl chloride, NEt₃, 2) DMAP / 1) toluene, room temperature, 18 h, 2) toluene, room temperature, 1 h

11: 92 percent / LiAlH₄ / diethyl ether / 1.5 h / 0 - 20 °C

12: 95 percent / KH, TBAI / tetrahydrofuran / 2 h / Heating

13: 75 percent / 1 M aq. HCl / methanol / 3 h / Ambient temperature

14: 71 percent / NEt₃, DMAP / CH₂Cl₂ / 26 h / Ambient temperature

15: 100 percent / K₂CO₃ / methanol / 2.5 h / Ambient temperature

With hydrogenchloride; dmap; potassium hydroxide; sodium chlorite; sodium dihydrogenphosphate; lithium aluminium tetrahydride; dipyridinium dichromate; n-butyllithium; 2-methyl-but-2-ene; oxalyl dichloride; 4 A molecular sieve; 2,4,6-trichlorobenzoyl chloride; hydrogen; tetra-(n-butyl)ammonium iodide; potassium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; Lindlar's catalyst; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; tert-butyl alcohol;

DOI:10.1016/S0040-4020(97)10253-8

Reference yield:

(2S,3S)-3-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2-methyl-butyraldehyde (201667-71-2) → (4S,5S,6R,1'R,1''S,2''S,3''S)-2,2-dimethyl-5-p-methoxybenzyloxy-4-(3'-p-methoxybenzyloxy-1'-methylpropyl)-6-(1'',2''-dimethyl-3'',4''-epoxybutyl)-1,3-dioxane (158817-33-5)

Guidance literature:

Multi-step reaction with 14 steps

1: 88 percent / BuLi / tetrahydrofuran; CH₂Cl₂ / 1 h / -78 °C

2: 98 percent / H₂ / Lindlar catalyst / methanol / 48 h / 760 Torr / Ambient temperature

3: 100 percent / DMAP, NEt₃ / CH₂Cl₂ / 15 h / Ambient temperature

4: 63 percent / DDQ / CH₂Cl₂; H₂O / 0.5 h / 0 °C

5: 90 percent / pyridinium dichromate, 4 Angstroem molecular sieves / CH₂Cl₂ / 2 h / Ambient temperature

6: NaClO₂, NaH₂PO₄*2H₂O, 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O / 1.5 h / 0 °C

7: 34.0 mg / KOH / methanol; H₂O / 24 h / Ambient temperature

8: 1) 2,4,6-trichlorobenzoyl chloride, NEt₃, 2) DMAP / 1) toluene, room temperature, 18 h, 2) toluene, room temperature, 1 h

10: 92 percent / LiAlH₄ / diethyl ether / 1.5 h / 0 - 20 °C

11: 95 percent / KH, TBAI / tetrahydrofuran / 2 h / Heating

12: 75 percent / 1 M aq. HCl / methanol / 3 h / Ambient temperature

13: 71 percent / NEt₃, DMAP / CH₂Cl₂ / 26 h / Ambient temperature

14: 100 percent / K₂CO₃ / methanol / 2.5 h / Ambient temperature

With hydrogenchloride; dmap; potassium hydroxide; sodium chlorite; sodium dihydrogenphosphate; lithium aluminium tetrahydride; dipyridinium dichromate; n-butyllithium; 2-methyl-but-2-ene; 4 A molecular sieve; 2,4,6-trichlorobenzoyl chloride; hydrogen; tetra-(n-butyl)ammonium iodide; potassium hydride; potassium carbonate; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; Lindlar's catalyst; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; tert-butyl alcohol;

DOI:10.1016/S0040-4020(97)10253-8

upstream raw materials:

(4S,5S,6R,1'R,1''S,2''S,3''S)-2,2-dimethyl-5-p-methoxybenzyloxy-4-(3'-p-methoxybenzyloxy-1'-methylpropyl)-6-[1'',2''-dimethyl-3''-hydroxy-4''-(2,4,6-triisopropylbenzenesulfonyloxy)butyl]-1,3-dioxane

(2S,3S)-3-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2-methyl-butan-1-ol

(2S,3S)-3-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2-methyl-butyraldehyde

(R)-1-methoxy-4-((3-methylpent-4-ynyloxy)methyl)benzene

Downstream raw materials:

(4S,5S,6R,1'R,1''S,2''S,3''S)-2,2-dimethyl-5-p-methoxybenzyloxy-4-(3'-p-methoxybenzyloxy-1'-methylpropyl)-6-(1'',2''-dimethyl-3''-hydroxy-5''-hexenyl)-1,3-dioxane

(5S,6S)-6-{(4R,5S,6S)-5-(4-Methoxy-benzyloxy)-6-[(R)-3-(4-methoxy-benzyloxy)-1-methyl-propyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-5-methyl-hept-1-en-4-one

(4S,5S,6R,1'R,1''S,2''S,3''S)-2,2-dimethyl-5-p-methoxybenzyloxy-4-(3'-p-methoxybenzyloxy-1'-methylpropyl)-6-(1'',2''-dimethyl-3''-hydroxy-5''-hexynyl)-1,3-dioxane