Methanesulfonic acid (1S,2R,4S)-6-(tert-butyl-diphenyl-silanyloxy)-2,4-dimethyl-1-((R)-1-methyl-3-trityloxy-propyl)-hexyl ester

Base Information

• Chemical Name: Methanesulfonic acid (1S,2R,4S)-6-(tert-butyl-diphenyl-silanyloxy)-2,4-dimethyl-1-((R)-1-methyl-3-trityloxy-propyl)-hexyl ester
• CAS No.: 105676-36-6
• Molecular Formula: C₄₈H₆₀O₅SSi
• Molecular Weight: 777.153

Synonyms:Methanesulfonic acid (1S,2R,4S)-6-(tert-butyl-diphenyl-silanyloxy)-2,4-dimethyl-1-((R)-1-methyl-3-trityloxy-propyl)-hexyl ester

Chemical Property of Methanesulfonic acid (1S,2R,4S)-6-(tert-butyl-diphenyl-silanyloxy)-2,4-dimethyl-1-((R)-1-methyl-3-trityloxy-propyl)-hexyl ester

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methanesulfonic acid (1S,2R,4S)-6-(tert-butyl-diphenyl-silanyloxy)-2,4-dimethyl-1-((R)-1-methyl-3-trityloxy-propyl)-hexyl ester

There total 38 articles about Methanesulfonic acid (1S,2R,4S)-6-(tert-butyl-diphenyl-silanyloxy)-2,4-dimethyl-1-((R)-1-methyl-3-trityloxy-propyl)-hexyl ester 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:

(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran (32780-06-6) → Methanesulfonic acid (1S,2R,4S)-6-(tert-butyl-diphenyl-silanyloxy)-2,4-dimethyl-1-((R)-1-methyl-3-trityloxy-propyl)-hexyl ester (105676-36-6)

Guidance literature:

Multi-step reaction with 29 steps

1: 71.5 percent / triethylamine, 4,4-dimethylaminopyridine / CH₂Cl₂ / 3.5 h / Ambient temperature

2: 1.) lithium hexamethyldisilazide / 1.) THF, hexane, -78 deg C, 25 min; 2.) THF, hexane

3: 30percent H₂O₂ / 0 °C

4: 1.) n-butyl lithium / 1.) THF, hexane, -78 deg C, 20 min; 2.) THF, hexane, -78 deg C, 30 min.

5: 1.) n-butyl lithium, hexamethyldisilazane 3.) oxodiperoxomolybdenum-pyridine-HMPA complex / 1.) THF, 0 deg C, 10 min; 2.) THF, -78 deg C, 20 min; 3.) THF, -60 deg C, 45 min.

6: 62 percent / Raney-nickel / methanol / 18 h / Ambient temperature

7: NaBH₄ / tetrahydrofuran; H₂O / 1 h / Ambient temperature

8: dimethoxypropane, conc. HCl / 1.5 h / Ambient temperature

9: 95 percent / tetra n-butylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature

10: 92 percent / pyridine / CH₂Cl₂ / 12 h / Ambient temperature

11: sodium methoxide / methanol / 0.5 h / 0 °C

12: 1.) n-butyl lithium, hexamethyldisilazane / 1.) THF, 0 deg C, 15 min; 2.) THF, RT, 1 h, 3.) THF, RT, 15 h

13: EDAC, DMAP / CH₂Cl₂ / 0.33 h

14: m-CPBA / CH₂Cl₂ / 0.33 h / -23 °C

15: pyridine, CaCO₃ / toluene / 1 h / Heating

16: 1.) CuBr*Me₂S / 1.) ether, 0 deg C, 10 min; 2.) ether, -23 deg C, 10 min.

17: LiAlH₄ / diethyl ether / 1 h / 25 °C

18: 86 percent / imidazole / dimethylformamide / 0.33 h / Ambient temperature

19: Et₃N / CH₂Cl₂ / 0.67 h / 0 °C

20: LiAlH₄ / diethyl ether / 2 h / Ambient temperature

21: 98 percent / 80percent aq. AcOH / 15 h / Ambient temperature

22: pyridine / CH₂Cl₂ / 1 h / Ambient temperature

23: NaOMe / methanol; CH₂Cl₂ / 0.33 h / Ambient temperature

24: 1.) hexamethyldisilazane, n-butyl lithium / 1.) THF, 0 deg C, 20 min; 2.) THF RT, 1 h, 3.) THF, RT, 15 h

25: EDAC / DMAP / CH₂Cl₂ / 0.5 h / Ambient temperature

26: 1.) CuBr*Me₂S / 1.) ether, 0 deg C, 5 min; 2.) ether, -23 deg C, 20 min.

27: 88 percent / LiAlH₄ / diethyl ether / 1 h / Ambient temperature

28: acetonitrile / 1 h / Ambient temperature

29: Et₃N / CH₂Cl₂ / 1 h / 0 °C

With pyridine; 1H-imidazole; hydrogenchloride; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; n-butyllithium; copper(I) bromide dimethylsulfide complex; MoO₅*pyridine*HMPA; dimethoxypropane; tetrabutyl ammonium fluoride; dihydrogen peroxide; sodium methylate; nickel; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; 1,1,1,3,3,3-hexamethyl-disilazane; calcium carbonate; lithium hexamethyldisilazane; dmap; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1016/S0040-4020(01)87683-3

Reference yield:

(5S)-5-(tert-butyldiphenylsiloxymethyl)-2(5H)-furanone (99315-76-1) → Methanesulfonic acid (1S,2R,4S)-6-(tert-butyl-diphenyl-silanyloxy)-2,4-dimethyl-1-((R)-1-methyl-3-trityloxy-propyl)-hexyl ester (105676-36-6)

Guidance literature:

Multi-step reaction with 25 steps

1: 86 percent / tetrahydrofuran / -78 °C

2: 85 percent / oxodiperoxymolybdenum(pyridine)hexamethylphosphoramide / tetrahydrofuran / -78 °C

3: 65 percent / Raney nickel / tetrahydrofuran

4: NaBH₄ / tetrahydrofuran; H₂O

5: H⁽¹⁺⁾ / acetone

6: 62 percent / Bu₄N⁽¹⁺⁾*F^(1-) / tetrahydrofuran

7: 92 percent / pyridine / 0 °C

8: 85 percent / NaOMe / methanol

9: tetrahydrofuran / 0 - 25 °C

10: EDAC*HCl, DMAP / CH₂Cl₂

11: 1) m-CPBA, 2) CaCO₃ / 1) CH₂Cl₂, - 23 deg C, 2) toluene, reflux

12: 91 percent / diethyl ether / -23 °C

13: 90 percent / LiAlH₄ / diethyl ether

14: 96 percent / DMAP, pyridine / CH₂Cl₂

15: Et₃N / CH₂Cl₂

16: LiAlH₄ / diethyl ether

17: aq. AcOH

18: pyridime

19: NaOMe / methanol

20: tetrahydrofuran / 0 - 25 °C

21: EDAC*HCl, DMPA / CH₂Cl₂

22: 1)H₂O₂, 2) CaCO₃ / 1) 0 deg C, CH₂Cl₂, 2) toluene, reflux

23: 88 percent / LiAlH₄ / diethyl ether

24: acetonitrile

25: Et₃N / CH₂Cl₂

With pyridine; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; MoO₅*pyridine*HMPA; 0,2,4-dichlorophenyl-0-methylisopropylamidothiophosphate; tetrabutyl ammonium fluoride; dihydrogen peroxide; sodium methylate; hydrogen cation; nickel; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; calcium carbonate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetone; acetonitrile;

Reference yield:

(3R,4S,5R)-5-((tert-butyldiphenylsilyloxy)methyl)-3,4-dihydroxydihydrofuran-2(3H)-one (92512-33-9) → Methanesulfonic acid (1S,2R,4S)-6-(tert-butyl-diphenyl-silanyloxy)-2,4-dimethyl-1-((R)-1-methyl-3-trityloxy-propyl)-hexyl ester (105676-36-6)

Guidance literature:

Multi-step reaction with 31 steps

1: tetrahydrofuran / 0.25 h / Ambient temperature

2: Raney nickel / tetrahydrofuran / 4 h / Heating

3: 71.5 percent / triethylamine, 4,4-dimethylaminopyridine / CH₂Cl₂ / 3.5 h / Ambient temperature

4: 1.) lithium hexamethyldisilazide / 1.) THF, hexane, -78 deg C, 25 min; 2.) THF, hexane

5: 30percent H₂O₂ / 0 °C

6: 1.) n-butyl lithium / 1.) THF, hexane, -78 deg C, 20 min; 2.) THF, hexane, -78 deg C, 30 min.

7: 1.) n-butyl lithium, hexamethyldisilazane 3.) oxodiperoxomolybdenum-pyridine-HMPA complex / 1.) THF, 0 deg C, 10 min; 2.) THF, -78 deg C, 20 min; 3.) THF, -60 deg C, 45 min.

8: 62 percent / Raney-nickel / methanol / 18 h / Ambient temperature

9: NaBH₄ / tetrahydrofuran; H₂O / 1 h / Ambient temperature

10: dimethoxypropane, conc. HCl / 1.5 h / Ambient temperature

11: 95 percent / tetra n-butylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature

12: 92 percent / pyridine / CH₂Cl₂ / 12 h / Ambient temperature

13: sodium methoxide / methanol / 0.5 h / 0 °C

14: 1.) n-butyl lithium, hexamethyldisilazane / 1.) THF, 0 deg C, 15 min; 2.) THF, RT, 1 h, 3.) THF, RT, 15 h

15: EDAC, DMAP / CH₂Cl₂ / 0.33 h

16: m-CPBA / CH₂Cl₂ / 0.33 h / -23 °C

17: pyridine, CaCO₃ / toluene / 1 h / Heating

18: 1.) CuBr*Me₂S / 1.) ether, 0 deg C, 10 min; 2.) ether, -23 deg C, 10 min.

19: LiAlH₄ / diethyl ether / 1 h / 25 °C

20: 86 percent / imidazole / dimethylformamide / 0.33 h / Ambient temperature

21: Et₃N / CH₂Cl₂ / 0.67 h / 0 °C

22: LiAlH₄ / diethyl ether / 2 h / Ambient temperature

23: 98 percent / 80percent aq. AcOH / 15 h / Ambient temperature

24: pyridine / CH₂Cl₂ / 1 h / Ambient temperature

25: NaOMe / methanol; CH₂Cl₂ / 0.33 h / Ambient temperature

26: 1.) hexamethyldisilazane, n-butyl lithium / 1.) THF, 0 deg C, 20 min; 2.) THF RT, 1 h, 3.) THF, RT, 15 h

27: EDAC / DMAP / CH₂Cl₂ / 0.5 h / Ambient temperature

28: 1.) CuBr*Me₂S / 1.) ether, 0 deg C, 5 min; 2.) ether, -23 deg C, 20 min.

29: 88 percent / LiAlH₄ / diethyl ether / 1 h / Ambient temperature

30: acetonitrile / 1 h / Ambient temperature

31: Et₃N / CH₂Cl₂ / 1 h / 0 °C

With pyridine; 1H-imidazole; hydrogenchloride; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; n-butyllithium; copper(I) bromide dimethylsulfide complex; MoO₅*pyridine*HMPA; dimethoxypropane; tetrabutyl ammonium fluoride; dihydrogen peroxide; sodium methylate; nickel; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; 1,1,1,3,3,3-hexamethyl-disilazane; calcium carbonate; lithium hexamethyldisilazane; dmap; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1016/S0040-4020(01)87683-3

upstream raw materials:

methanesulfonyl chloride

(3R,4S,5R,7S)-9-(tert-Butyl-diphenyl-silanyloxy)-3,5,7-trimethyl-1-trityloxy-nonan-4-ol

(2S,3R)-3-<(4S)-2,2-dimethyl-1,3-dioxolan-4-yl>-1,2-butanediol

(4S,5S)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-3-hydroxy-4-methyldihydrofuran-2(3H)-one

Downstream raw materials:

(3R,5S,7S)-1,9-dihydroxy-3,5,7-trimethyl-9-O-tert-butyldiphenylsilyl-1-O-triphenylmethyl-nonane

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