2-{(4S,6R)-6-[(S)-4-(tert-Butyl-diphenyl-silanyloxy)-2-methoxymethoxy-butyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-2-methyl-propan-1-ol

Base Information

• Chemical Name: 2-{(4S,6R)-6-[(S)-4-(tert-Butyl-diphenyl-silanyloxy)-2-methoxymethoxy-butyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-2-methyl-propan-1-ol
• CAS No.: 111043-56-2
• Molecular Formula: C₃₂H₅₀O₆Si
• Molecular Weight: 558.831
• Mol file: 111043-56-2.mol

Synonyms:2-{(4S,6R)-6-[(S)-4-(tert-Butyl-diphenyl-silanyloxy)-2-methoxymethoxy-butyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-2-methyl-propan-1-ol

Chemical Property of 2-{(4S,6R)-6-[(S)-4-(tert-Butyl-diphenyl-silanyloxy)-2-methoxymethoxy-butyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-2-methyl-propan-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-{(4S,6R)-6-[(S)-4-(tert-Butyl-diphenyl-silanyloxy)-2-methoxymethoxy-butyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-2-methyl-propan-1-ol

There total 30 articles about 2-{(4S,6R)-6-[(S)-4-(tert-Butyl-diphenyl-silanyloxy)-2-methoxymethoxy-butyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-2-methyl-propan-1-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: 88.0%

{(S)-4-[(4R,6S)-6-(2-Benzyloxy-1,1-dimethyl-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-3-methoxymethoxy-butoxy}-tert-butyl-diphenyl-silane (121372-79-0) → 2-{(4S,6R)-6-[(S)-4-(tert-Butyl-diphenyl-silanyloxy)-2-methoxymethoxy-butyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-2-methyl-propan-1-ol (111043-56-2)

Guidance literature:

With W-2 Raney nickel; In ethanol; at 50 ℃; for 4h;

DOI:10.1021/jo00273a009

Reference yield:

5,5-dimethyl-2-phenyl-[1,3]dioxane (776-88-5) → 2-{(4S,6R)-6-[(S)-4-(tert-Butyl-diphenyl-silanyloxy)-2-methoxymethoxy-butyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-2-methyl-propan-1-ol (111043-56-2)

Guidance literature:

Multi-step reaction with 21 steps

1: 94 percent / BH₃*THF / tetrahydrofuran / 72 h / Heating

2: 82 percent / PCC / CH₂Cl₂ / 11 h / 25 °C

3: 1.) NaH / 1.) toluene, 0 deg C, 1 h, 2.) THF, RT, 6 h

4: 79 percent / DIBAL / diethyl ether; toluene / 25 °C

5: 1.) titanium(IV) isopropoxide, (-)-diethyl D-tartrate, 2.) tert-butyl hydroperoxide / 1.) CH₂Cl₂, -40 deg C, 30 min, 2.) toluene, 0 deg C, 8 h

6: oxalyl chloride / dimethylsulfoxide; CH₂Cl₂ / 1.5 h / -78 °C

7: tetrahydrofuran; benzene / 12 h / 0 °C

8: 93 percent / NaBH₄ / methanol / 6 h / -20 °C

9: 1.) (+)-DET, Ti(iPrO)4, 2.) TBHP / 1.) CH₂Cl₂, 4-Angstroem molecular sieves, -40 deg C, 30 min, 2.) from -40 deg C to 0 deg C, 12 h

10: Red-Al / tetrahydrofuran; toluene / 48 h / Ambient temperature

11: pyridine / CH₂Cl₂ / 4 h / 0 °C

12: 94 percent / p-TsOH / CH₂Cl₂ / 2 h / 24 °C

13: 95 percent / DIBAL / diethyl ether; hexane / 1 h / -78 °C

14: oxalyl chloride / dimethylsulfoxide; CH₂Cl₂ / 1 h / -78 °C

15: 1.) NaH / 1.) toluene, 0 deg C, 1 h, 2.) THF, 0 deg C, 10 h

16: 87 percent / DIBAL / diethyl ether; hexane / 2 h / -78 °C

17: 1.) (-)-DET, Ti(iPrO)4, 2.) TBHP / 1.) CH₂Cl₂, 4-Angstroem molecular sieves, -40 deg C, 30 min, 2.) toluene, from -40 deg C to 0 deg C, 7 h

18: Red-Al / tetrahydrofuran; toluene / 72 h / -23 - -20 °C

19: imidazole / dimethylformamide / 5 h / Ambient temperature

20: 85 percent / diisopropylamine / 15 h / Ambient temperature

21: 88 percent / W-2 Raney nickel / ethanol / 4 h / 50 °C

With pyridine; 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium tetrahydroborate; borane-THF; oxalyl dichloride; diethyl (2S,3S)-tartrate; diethyl (2R,3R)-tartrate; W-2 Raney nickel; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; (-)-diethyl tartrate; diisopropylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; pyridinium chlorochromate; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; benzene;

DOI:10.1021/jo00273a009

Reference yield:

3-benzyloxypivalic aldehyde (38216-93-2) → 2-{(4S,6R)-6-[(S)-4-(tert-Butyl-diphenyl-silanyloxy)-2-methoxymethoxy-butyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-2-methyl-propan-1-ol (111043-56-2)

Guidance literature:

Multi-step reaction with 19 steps

1: 1.) NaH / 1.) toluene, 0 deg C, 1 h, 2.) THF, RT, 6 h

2: 79 percent / DIBAL / diethyl ether; toluene / 25 °C

3: 1.) titanium(IV) isopropoxide, (-)-diethyl D-tartrate, 2.) tert-butyl hydroperoxide / 1.) CH₂Cl₂, -40 deg C, 30 min, 2.) toluene, 0 deg C, 8 h

4: oxalyl chloride / dimethylsulfoxide; CH₂Cl₂ / 1.5 h / -78 °C

5: tetrahydrofuran; benzene / 12 h / 0 °C

6: 93 percent / NaBH₄ / methanol / 6 h / -20 °C

7: 1.) (+)-DET, Ti(iPrO)4, 2.) TBHP / 1.) CH₂Cl₂, 4-Angstroem molecular sieves, -40 deg C, 30 min, 2.) from -40 deg C to 0 deg C, 12 h

8: Red-Al / tetrahydrofuran; toluene / 48 h / Ambient temperature

9: pyridine / CH₂Cl₂ / 4 h / 0 °C

10: 94 percent / p-TsOH / CH₂Cl₂ / 2 h / 24 °C

11: 95 percent / DIBAL / diethyl ether; hexane / 1 h / -78 °C

12: oxalyl chloride / dimethylsulfoxide; CH₂Cl₂ / 1 h / -78 °C

13: 1.) NaH / 1.) toluene, 0 deg C, 1 h, 2.) THF, 0 deg C, 10 h

14: 87 percent / DIBAL / diethyl ether; hexane / 2 h / -78 °C

15: 1.) (-)-DET, Ti(iPrO)4, 2.) TBHP / 1.) CH₂Cl₂, 4-Angstroem molecular sieves, -40 deg C, 30 min, 2.) toluene, from -40 deg C to 0 deg C, 7 h

16: Red-Al / tetrahydrofuran; toluene / 72 h / -23 - -20 °C

17: imidazole / dimethylformamide / 5 h / Ambient temperature

18: 85 percent / diisopropylamine / 15 h / Ambient temperature

19: 88 percent / W-2 Raney nickel / ethanol / 4 h / 50 °C

With pyridine; 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium tetrahydroborate; oxalyl dichloride; diethyl (2S,3S)-tartrate; diethyl (2R,3R)-tartrate; W-2 Raney nickel; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; (-)-diethyl tartrate; diisopropylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; benzene;

DOI:10.1021/jo00273a009

upstream raw materials:

{(S)-4-[(4R,6S)-6-(2-Benzyloxy-1,1-dimethyl-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-3-methoxymethoxy-butoxy}-tert-butyl-diphenyl-silane

5,5-dimethyl-2-phenyl-[1,3]dioxane

3-(benzyloxy)-2,2-dimethylpropan-1-ol

3-benzyloxypivalic aldehyde

Downstream raw materials:

2-{(4S,6R)-6-[(S)-4-(tert-Butyl-diphenyl-silanyloxy)-2-methoxymethoxy-butyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-2-methyl-propionaldehyde

3-{(4S,6R)-6-[(S)-4-(tert-Butyl-diphenyl-silanyloxy)-2-methoxymethoxy-butyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-3-methyl-butan-2-ol

3-{(4S,6R)-6-[(S)-4-(tert-Butyl-diphenyl-silanyloxy)-2-methoxymethoxy-butyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-3-methyl-butan-2-one

(R)-7-[2-(tert-Butyl-diphenyl-silanyloxy)-eth-(E)-ylidene]-2-{(4S,6R)-6-[(S)-4-(tert-butyl-diphenyl-silanyloxy)-2-methoxymethoxy-butyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-5-hydroxy-2-methyl-dec-9-en-3-one