Toluene-4-sulfonic acid (1S,3aS,6S,6aR)-6-((R)-5-ethyl-2-methyl-3-oxo-2,3-dihydro-furan-2-ylmethyl)-4-isopropylidene-3a-methyl-3-oxo-tetrahydro-furo[3,4-c]furan-1-ylmethyl ester

Base Information

Chemical Name:Toluene-4-sulfonic acid (1S,3aS,6S,6aR)-6-((R)-5-ethyl-2-methyl-3-oxo-2,3-dihydro-furan-2-ylmethyl)-4-isopropylidene-3a-methyl-3-oxo-tetrahydro-furo[3,4-c]furan-1-ylmethyl ester
CAS No.:137792-33-7
Molecular Formula:C₂₆H₃₂O₈S
Molecular Weight:504.601
Hs Code.:

Toluene-4-sulfonic acid (1S,3aS,6S,6aR)-6-((R)-5-ethyl-2-methyl-3-oxo-2,3-dihydro-furan-2-ylmethyl)-4-isopropylidene-3a-methyl-3-oxo-tetrahydro-furo[3,4-c]furan-1-ylmethyl ester

Synonyms:Toluene-4-sulfonic acid (1S,3aS,6S,6aR)-6-((R)-5-ethyl-2-methyl-3-oxo-2,3-dihydro-furan-2-ylmethyl)-4-isopropylidene-3a-methyl-3-oxo-tetrahydro-furo[3,4-c]furan-1-ylmethyl ester

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Chemical Property of Toluene-4-sulfonic acid (1S,3aS,6S,6aR)-6-((R)-5-ethyl-2-methyl-3-oxo-2,3-dihydro-furan-2-ylmethyl)-4-isopropylidene-3a-methyl-3-oxo-tetrahydro-furo[3,4-c]furan-1-ylmethyl ester

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Technology Process of Toluene-4-sulfonic acid (1S,3aS,6S,6aR)-6-((R)-5-ethyl-2-methyl-3-oxo-2,3-dihydro-furan-2-ylmethyl)-4-isopropylidene-3a-methyl-3-oxo-tetrahydro-furo[3,4-c]furan-1-ylmethyl ester

There total 14 articles about Toluene-4-sulfonic acid (1S,3aS,6S,6aR)-6-((R)-5-ethyl-2-methyl-3-oxo-2,3-dihydro-furan-2-ylmethyl)-4-isopropylidene-3a-methyl-3-oxo-tetrahydro-furo[3,4-c]furan-1-ylmethyl 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: 57.0%

: 137769-70-1
(3S,3aR,4S,6aS)-4-((R)-5-Ethyl-2-methyl-3-oxo-2,3-dihydro-furan-2-ylmethyl)-3-hydroxymethyl-6-isopropylidene-6a-methyl-tetrahydro-furo[3,4-c]furan-1-one

: 98-59-9
p-toluenesulfonyl chloride

: 137792-33-7
Toluene-4-sulfonic acid (1S,3aS,6S,6aR)-6-((R)-5-ethyl-2-methyl-3-oxo-2,3-dihydro-furan-2-ylmethyl)-4-isopropylidene-3a-methyl-3-oxo-tetrahydro-furo[3,4-c]furan-1-ylmethyl ester

Guidance literature:: With pyridine; In chloroform; at 25 ℃; for 24h;
DOI:10.1021/ja00025a049

Reference yield:

: (4R,5S)-5-Benzyloxy-4-((R)-6-hydroxy-3-methyl-1-methylene-4-oxo-3-trimethylsilanyloxy-octyl)-dihydro-furan-2-one

: 137792-33-7
Toluene-4-sulfonic acid (1S,3aS,6S,6aR)-6-((R)-5-ethyl-2-methyl-3-oxo-2,3-dihydro-furan-2-ylmethyl)-4-isopropylidene-3a-methyl-3-oxo-tetrahydro-furo[3,4-c]furan-1-ylmethyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

2: 5percent aq. HCl / tetrahydrofuran / 8 h / 25 °C

3: 93 percent / OsO₄, NaIO₄ / tetrahydrofuran; H₂O / 12 h / 25 °C

4: NaBH₄ / methanol / 0.25 h / -40 °C

5: 81 percent / P₂O₅, molecular sieves / CH₂Cl₂ / 0.67 h / 25 °C

6: 1.) LDA / 1.) THF, -78 deg C, 40 min, 2.) THF, -78 deg C, 1.5 h

7: 1.) NaH / 1.) DMF, 0 deg C, 40 min, 2.) DMF, 0 deg C, 3.5 h

8: 1.) TMSBr, 4 Angstroem molecular sieves, 2.) Amberlyst-15, 4 Angstroem molecular sieves / 1.) CH₂Cl₂, from 0 to 25 deg C, 5 h, 2.) CH₂Cl₂, 25 deg C, 10 h

9: 99 percent / H₂ / 10percent Pd/C / methanol / 4 h / 760 Torr

10: 57 percent / pyridine / CHCl₃ / 24 h / 25 °C

With pyridine; hydrogenchloride; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; molecular sieve; amberlyst-15; trimethylsilyl bromide; 4 A molecular sieve; hydrogen; phosphorus pentoxide; sodium hydride; Dess-Martin periodane; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; chloroform; water;
DOI:10.1021/ja00025a049

Reference yield:

: (R)-8-((2S,3R)-2-Benzyloxy-5-oxo-tetrahydro-furan-3-yl)-6-methyl-6-trimethylsilanyloxy-non-8-ene-3,5-dione

: 137792-33-7
Toluene-4-sulfonic acid (1S,3aS,6S,6aR)-6-((R)-5-ethyl-2-methyl-3-oxo-2,3-dihydro-furan-2-ylmethyl)-4-isopropylidene-3a-methyl-3-oxo-tetrahydro-furo[3,4-c]furan-1-ylmethyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 5percent aq. HCl / tetrahydrofuran / 8 h / 25 °C

2: 93 percent / OsO₄, NaIO₄ / tetrahydrofuran; H₂O / 12 h / 25 °C

3: NaBH₄ / methanol / 0.25 h / -40 °C

4: 81 percent / P₂O₅, molecular sieves / CH₂Cl₂ / 0.67 h / 25 °C

5: 1.) LDA / 1.) THF, -78 deg C, 40 min, 2.) THF, -78 deg C, 1.5 h

6: 1.) NaH / 1.) DMF, 0 deg C, 40 min, 2.) DMF, 0 deg C, 3.5 h

7: 1.) TMSBr, 4 Angstroem molecular sieves, 2.) Amberlyst-15, 4 Angstroem molecular sieves / 1.) CH₂Cl₂, from 0 to 25 deg C, 5 h, 2.) CH₂Cl₂, 25 deg C, 10 h

8: 99 percent / H₂ / 10percent Pd/C / methanol / 4 h / 760 Torr

9: 57 percent / pyridine / CHCl₃ / 24 h / 25 °C

With pyridine; hydrogenchloride; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; molecular sieve; amberlyst-15; trimethylsilyl bromide; 4 A molecular sieve; hydrogen; phosphorus pentoxide; sodium hydride; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; chloroform; water;
DOI:10.1021/ja00025a049