Toluene-4-sulfonic acid (R)-2-hydroxy-2-[(2R,5R)-5-((S)-2-oxo-[1,3]dioxolan-4-yl)-tetrahydro-furan-2-yl]-ethyl ester

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Chemical Name:Toluene-4-sulfonic acid (R)-2-hydroxy-2-[(2R,5R)-5-((S)-2-oxo-[1,3]dioxolan-4-yl)-tetrahydro-furan-2-yl]-ethyl ester
CAS No.:183308-64-7
Molecular Formula:C₁₆H₂₀O₈S
Molecular Weight:372.396
Hs Code.:

Synonyms:Toluene-4-sulfonic acid (R)-2-hydroxy-2-[(2R,5R)-5-((S)-2-oxo-[1,3]dioxolan-4-yl)-tetrahydro-furan-2-yl]-ethyl ester

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Chemical Property of Toluene-4-sulfonic acid (R)-2-hydroxy-2-[(2R,5R)-5-((S)-2-oxo-[1,3]dioxolan-4-yl)-tetrahydro-furan-2-yl]-ethyl ester

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Technology Process of Toluene-4-sulfonic acid (R)-2-hydroxy-2-[(2R,5R)-5-((S)-2-oxo-[1,3]dioxolan-4-yl)-tetrahydro-furan-2-yl]-ethyl ester

There total 1 articles about Toluene-4-sulfonic acid (R)-2-hydroxy-2-[(2R,5R)-5-((S)-2-oxo-[1,3]dioxolan-4-yl)-tetrahydro-furan-2-yl]-ethyl 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: 72.0%

: 98-59-9
p-toluenesulfonyl chloride

: (S)-4-[(R)-5-(1,2-Dihydroxy-ethyl)-tetrahydro-furan-2-yl]-[1,3]dioxolan-2-one

: 183308-64-7
Toluene-4-sulfonic acid (R)-2-hydroxy-2-[(2R,5R)-5-((S)-2-oxo-[1,3]dioxolan-4-yl)-tetrahydro-furan-2-yl]-ethyl ester

Guidance literature:: With Bu₂Sn(OMe)3; triethylamine; In toluene;
DOI:10.1016/0040-4039(96)01589-4

Reference yield:

: 183308-64-7
Toluene-4-sulfonic acid (R)-2-hydroxy-2-[(2R,5R)-5-((S)-2-oxo-[1,3]dioxolan-4-yl)-tetrahydro-furan-2-yl]-ethyl ester

: Toluene-4-sulfonic acid (S)-2-{(2R,5R,2'R,5'R)-5'-[(1S,5S)-5-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-undecyl]-octahydro-[2,2']bifuranyl-5-yl}-2-hydroxy-ethyl ester

Guidance literature:: Multi-step reaction with 13 steps

1: 98 percent / DBU / CH₂Cl₂

2: 1.) NaOMe, 2.) PPTS / 1.) MeOH, 2.) acetone

3: 91 percent / diethyl ether / 0 °C

4: 98 percent / pyridine / CH₂Cl₂

5: 82 percent / t-BuLi / tetrahydrofuran / -78 deg C -> RT

6: 85 percent / Red-Al / diethyl ether / Ambient temperature

7: 92 percent / L-(+)-diethyl tartrate / CH₂Cl₂ / -25 °C

8: 96 percent / NEt₃

9: 1.) H₂SiF₆, 2.) 2,2-dimethoxypropane, PPTS, 3.) K₂CO₃ / 1.) CH₃CN, RT, 2.) acetone, 3.) MeOH

10: 1.) t-BuLi, 2.) BF₃*OEt₂ / 1.) THF, 2.) THF, -78 deg C, 30 min

11: 95 percent / hydrogen / Pd/C / ethyl acetate / 760 Torr / Ambient temperature

12: 80percent AcOH

13: Bu₂Sn(OMe)2, NEt₃ / toluene

With pyridine; fluorosilicic acid; diethyl (2R,3R)-tartrate; boron trifluoride diethyl etherate; hydrogen; tert.-butyl lithium; sodium methylate; pyridinium p-toluenesulfonate; dibutyldimethoxytin; potassium carbonate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; 2,2-dimethoxy-propane; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; toluene;
DOI:10.1016/0040-4039(96)01589-4

Reference yield:

: 183308-64-7
Toluene-4-sulfonic acid (R)-2-hydroxy-2-[(2R,5R)-5-((S)-2-oxo-[1,3]dioxolan-4-yl)-tetrahydro-furan-2-yl]-ethyl ester

: (S)-3-((S)-13-{(2R,5R,2'R,5'R)-5'-[(1S,5S)-1,5-Bis-(tert-butyl-dimethyl-silanyloxy)-undecyl]-octahydro-[2,2']bifuranyl-5-yl}-13-hydroxy-tridecyl)-5-methyl-3-phenylsulfanyl-dihydro-furan-2-one

Guidance literature:: Multi-step reaction with 17 steps

1: 98 percent / DBU / CH₂Cl₂

2: 1.) NaOMe, 2.) PPTS / 1.) MeOH, 2.) acetone

3: 91 percent / diethyl ether / 0 °C

4: 98 percent / pyridine / CH₂Cl₂

5: 82 percent / t-BuLi / tetrahydrofuran / -78 deg C -> RT

6: 85 percent / Red-Al / diethyl ether / Ambient temperature

7: 92 percent / L-(+)-diethyl tartrate / CH₂Cl₂ / -25 °C

8: 96 percent / NEt₃

9: 1.) H₂SiF₆, 2.) 2,2-dimethoxypropane, PPTS, 3.) K₂CO₃ / 1.) CH₃CN, RT, 2.) acetone, 3.) MeOH

10: 1.) t-BuLi, 2.) BF₃*OEt₂ / 1.) THF, 2.) THF, -78 deg C, 30 min

11: 95 percent / hydrogen / Pd/C / ethyl acetate / 760 Torr / Ambient temperature

12: 80percent AcOH

13: Bu₂Sn(OMe)2, NEt₃ / toluene

14: TBAF / tetrahydrofuran / Ambient temperature

15: AgNO₃, pyridine / tetrahydrofuran / Ambient temperature

16: 60 percent / t-BuLi, BF₃*OEt₂ / toluene / 0.5 h / -78 °C

17: 95 percent / (Ph₃P)3RhCl, H₂ / benzene / Ambient temperature

With pyridine; Wilkinson's catalyst; fluorosilicic acid; diethyl (2R,3R)-tartrate; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; tert.-butyl lithium; sodium methylate; pyridinium p-toluenesulfonate; dibutyldimethoxytin; potassium carbonate; silver nitrate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; 2,2-dimethoxy-propane; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; toluene; benzene;
DOI:10.1016/0040-4039(96)01589-4