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

Base Information

• Chemical Name: 2-<(1R,4S,6R)-4,6-bis(tert-butyl-dimethylsilyloxy)-1,5,5-trimethyl-8-(phenylsulfonyl)octyl>-1,3-dithiane
• CAS No.: 111080-13-8
• Molecular Formula: C₃₃H₆₂O₄S₃Si₂
• Molecular Weight: 675.222
• Mol file: 111080-13-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 50 articles about 2-<(1R,4S,6R)-4,6-bis(tert-butyl-dimethylsilyloxy)-1,5,5-trimethyl-8-(phenylsulfonyl)octyl>-1,3-dithiane 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: 86.0%

t-butyldimethylsiyl triflate (69739-34-0) + (3R,5S,8R)-1-Benzenesulfonyl-8-[1,3]dithian-2-yl-4,4-dimethyl-nonane-3,5-diol (116903-81-2) → 2-<(1R,4S,6R)-4,6-bis(tert-butyl-dimethylsilyloxy)-1,5,5-trimethyl-8-(phenylsulfonyl)octyl>-1,3-dithiane (111080-13-8)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; for 3h; Ambient temperature;

DOI:10.1016/S0040-4020(01)81517-9

Reference yield:

2-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2-methyl-propionaldehyde (105447-17-4) → 2-<(1R,4S,6R)-4,6-bis(tert-butyl-dimethylsilyloxy)-1,5,5-trimethyl-8-(phenylsulfonyl)octyl>-1,3-dithiane (111080-13-8)

Guidance literature:

Multi-step reaction with 23 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

16: 94 percent / n-Bu₄NF / tetrahydrofuran

17: H₂ / 5percent Rh-Al₂O₃ / tetrahydrofuran / 760 Torr

18: imidazol / dimethylformamide

19: 97 percent / n-bu4NF / tetrahydrofuran

20: 91 percent / KH, TsCl / dimethylformamide; tetrahydrofuran

21: n-BuLi, BF_3.Et₂O / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 °C

22: BF_3.Et₂O / CH₂Cl₂ / 0 °C

23: 2,6-lutidine / CH₂Cl₂

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; hydrogenchloride; dmap; sodium tetrahydroborate; n-butyllithium; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; potassium hydride; L-Selectride; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; p-toluenesulfonyl chloride; pyridinium chlorochromate; lithium diisopropyl amide; rhodium on alumina; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; 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) → 2-<(1R,4S,6R)-4,6-bis(tert-butyl-dimethylsilyloxy)-1,5,5-trimethyl-8-(phenylsulfonyl)octyl>-1,3-dithiane (111080-13-8)

Guidance literature:

Multi-step reaction with 21 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

14: 94 percent / n-Bu₄NF / tetrahydrofuran

15: H₂ / 5percent Rh-Al₂O₃ / tetrahydrofuran / 760 Torr

16: imidazol / dimethylformamide

17: 97 percent / n-bu4NF / tetrahydrofuran

18: 91 percent / KH, TsCl / dimethylformamide; tetrahydrofuran

19: n-BuLi, BF_3.Et₂O / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 °C

20: BF_3.Et₂O / CH₂Cl₂ / 0 °C

21: 2,6-lutidine / CH₂Cl₂

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; hydrogenchloride; dmap; sodium tetrahydroborate; n-butyllithium; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; potassium hydride; L-Selectride; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; p-toluenesulfonyl chloride; pyridinium chlorochromate; lithium diisopropyl amide; rhodium on alumina; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; N,N-dimethyl-formamide; toluene; benzene;

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

upstream raw materials:

t-butyldimethylsiyl triflate

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

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

Downstream raw materials:

Benzoic acid (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)-decyl ester

(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

Refernces

• 1、 Matsuda, Fuyuhiko,Tomiyosi, Nobuya,Yanagiya, Mitsutoshi,Matsumoto, Takeshi. "A Formal Synthesis of Aplasmomycin. Assembly of the C3-C17 Segment Based on Remote Controlled Asymmetric Reductions". . p. 2097 - 2100. Retrieved 2007/10/02.