(S)-3-((2S,6R)-6-tert-Butoxy-5-methyl-3,6-dihydro-2H-pyran-2-yl)-1-(tert-butyl-diphenyl-silanyloxy)-3-methyl-butan-2-ol

Base Information

• Chemical Name: (S)-3-((2S,6R)-6-tert-Butoxy-5-methyl-3,6-dihydro-2H-pyran-2-yl)-1-(tert-butyl-diphenyl-silanyloxy)-3-methyl-butan-2-ol
• CAS No.: 111080-18-3
• Molecular Formula: C₃₁H₄₆O₄Si
• Molecular Weight: 510.789

Synonyms:

Chemical Property of (S)-3-((2S,6R)-6-tert-Butoxy-5-methyl-3,6-dihydro-2H-pyran-2-yl)-1-(tert-butyl-diphenyl-silanyloxy)-3-methyl-butan-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-3-((2S,6R)-6-tert-Butoxy-5-methyl-3,6-dihydro-2H-pyran-2-yl)-1-(tert-butyl-diphenyl-silanyloxy)-3-methyl-butan-2-ol

There total 18 articles about (S)-3-((2S,6R)-6-tert-Butoxy-5-methyl-3,6-dihydro-2H-pyran-2-yl)-1-(tert-butyl-diphenyl-silanyloxy)-3-methyl-butan-2-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:

2-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2-methyl-propionaldehyde (105447-17-4) → (S)-3-((2S,6R)-6-tert-Butoxy-5-methyl-3,6-dihydro-2H-pyran-2-yl)-1-(tert-butyl-diphenyl-silanyloxy)-3-methyl-butan-2-ol (111080-18-3)

Guidance literature:

Multi-step reaction with 15 steps

1: LDA / tetrahydrofuran / -78 °C

2: c. HCl / methanol; H₂O

3: imidazole / dimethylformamide

4: PPTS / CH₂Cl₂

5: LDA / tetrahydrofuran / -78 °C

6: CSA / CH₂Cl₂

7: PCC / CH₂Cl₂ / in presence of 3A-MS

8: 87 percent / L-Selectride / tetrahydrofuran / -78 °C

9: 1N HCl / tetrahydrofuran

10: NaBH₄ / methanol

11: CSA / benzene / 30 °C

12: DMAP, pyridine

13: DBU / benzene

14: DIBAH / toluene / -78 °C

15: PPTS / CH₂Cl₂

With pyridine; 1H-imidazole; hydrogenchloride; dmap; sodium tetrahydroborate; camphor-10-sulfonic acid; pyridinium p-toluenesulfonate; L-Selectride; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; pyridinium chlorochromate; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; benzene;

DOI:10.1016/S0040-4039(00)87805-3

Reference yield:

(S)-4-Hydroxy-6-hydroxymethyl-5,5-dimethyl-tetrahydro-pyran-2-one (105447-19-6) → (S)-3-((2S,6R)-6-tert-Butoxy-5-methyl-3,6-dihydro-2H-pyran-2-yl)-1-(tert-butyl-diphenyl-silanyloxy)-3-methyl-butan-2-ol (111080-18-3)

Guidance literature:

Multi-step reaction with 13 steps

1: imidazole / dimethylformamide

2: PPTS / CH₂Cl₂

3: LDA / tetrahydrofuran / -78 °C

4: CSA / CH₂Cl₂

5: PCC / CH₂Cl₂ / in presence of 3A-MS

6: 87 percent / L-Selectride / tetrahydrofuran / -78 °C

7: 1N HCl / tetrahydrofuran

8: NaBH₄ / methanol

9: CSA / benzene / 30 °C

10: DMAP, pyridine

11: DBU / benzene

12: DIBAH / toluene / -78 °C

13: PPTS / CH₂Cl₂

With pyridine; 1H-imidazole; hydrogenchloride; dmap; sodium tetrahydroborate; camphor-10-sulfonic acid; pyridinium p-toluenesulfonate; L-Selectride; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; pyridinium chlorochromate; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; benzene;

DOI:10.1016/S0040-4039(00)87805-3

Reference yield:

4-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-4-methyl-pentanoic acid tert-butyl ester (105447-18-5,111139-42-5,111139-44-7) → (S)-3-((2S,6R)-6-tert-Butoxy-5-methyl-3,6-dihydro-2H-pyran-2-yl)-1-(tert-butyl-diphenyl-silanyloxy)-3-methyl-butan-2-ol (111080-18-3)

Guidance literature:

Multi-step reaction with 14 steps

1: c. HCl / methanol; H₂O

2: imidazole / dimethylformamide

3: PPTS / CH₂Cl₂

4: LDA / tetrahydrofuran / -78 °C

5: CSA / CH₂Cl₂

6: PCC / CH₂Cl₂ / in presence of 3A-MS

7: 87 percent / L-Selectride / tetrahydrofuran / -78 °C

8: 1N HCl / tetrahydrofuran

9: NaBH₄ / methanol

10: CSA / benzene / 30 °C

11: DMAP, pyridine

12: DBU / benzene

13: DIBAH / toluene / -78 °C

14: PPTS / CH₂Cl₂

With pyridine; 1H-imidazole; hydrogenchloride; dmap; sodium tetrahydroborate; camphor-10-sulfonic acid; pyridinium p-toluenesulfonate; L-Selectride; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; pyridinium chlorochromate; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; benzene;

DOI:10.1016/S0040-4039(00)87805-3

upstream raw materials:

tert-butyl alcohol

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

(S)-4-Hydroxy-6-hydroxymethyl-5,5-dimethyl-tetrahydro-pyran-2-one

4-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-4-methyl-pentanoic acid tert-butyl ester

Downstream raw materials:

(3R,5S,8R)-1-Benzenesulfonyl-8-[1,3]dithian-2-yl-4,4-dimethyl-nonane-3,5-diol

2-<(1R,4S,6R)-4,6-bis(tert-butyl-dimethylsilyloxy)-1,5,5-trimethyl-8-(phenylsulfonyl)octyl>-1,3-dithiane

(R)-1-Benzenesulfonyl-4-((2S,5R,6R)-6-tert-butoxy-5-methyl-tetrahydro-pyran-2-yl)-4-methyl-pentan-3-ol

(4R,6S,9R)-2-Benzenesulfonyl-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-9-[1,3]dithian-2-yl-5,5-dimethyl-1-((2S,4S,5R)-5-methyl-4-triisopropylsilanyloxy-tetrahydro-furan-2-yl)-decan-1-ol

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