1,2-O-(S)-pivalidene-7,24,27-tri-O-benzylokadaic acid

Base Information

Chemical Name:1,2-O-(S)-pivalidene-7,24,27-tri-O-benzylokadaic acid
CAS No.:194039-27-5
Molecular Formula:C₇₀H₉₄O₁₃
Molecular Weight:1143.51
Hs Code.:

Synonyms:1,2-O-(S)-pivalidene-7,24,27-tri-O-benzylokadaic acid

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Chemical Property of 1,2-O-(S)-pivalidene-7,24,27-tri-O-benzylokadaic acid

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Technology Process of 1,2-O-(S)-pivalidene-7,24,27-tri-O-benzylokadaic acid

There total 38 articles about 1,2-O-(S)-pivalidene-7,24,27-tri-O-benzylokadaic acid 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:

: 194039-24-2
C₇₁H₉₆O₁₄

: 194039-27-5
1,2-O-(S)-pivalidene-7,24,27-tri-O-benzylokadaic acid

Guidance literature:: With BH₃ system; toluene-4-sulfonic acid; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; Yield given. Multistep reaction; 1.), 2.) benzene;
DOI:10.1021/ja9715206

Reference yield:

: 194038-95-4
{(S)-1-[(R)-2-(4-Methoxy-benzyloxy)-1-methyl-ethyl]-but-3-ynyloxy}-trimethyl-silane

: 194039-27-5
1,2-O-(S)-pivalidene-7,24,27-tri-O-benzylokadaic acid

Guidance literature:: Multi-step reaction with 14 steps

1: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 20 min, 2.) THF, hexane, -78 deg C, 40 min

2: imidazole / CH₂Cl₂ / 0.75 h

3: 1.) CuI / 1.) Et₂O, from -78 to -40 deg C, 2.) Et₂O, -78 deg C, 2.5 h

4: p-TsOH*H₂O / benzene / 11 h / Ambient temperature

5: 98 percent / TBAF / tetrahydrofuran

6: 86 percent / Dess-Martin periodinane

7: 1.) LDA / 1.) THF, hexane, -78 deg C, 20 min, 2.) THF, hexane, -78 deg C, 15 min

8: 1.) NaH

9: n-Bu₃SnH, AIBN / toluene / 2 h / 80 °C

10: 77 percent / aq. Na₂PO₄ buffer, DDQ / CH₂Cl₂; 2-methyl-propan-2-ol / 0.05 h / Irradiation

11: 90 percent / Dess-Marti periodinane, NaHCO₃ / CH₂Cl₂ / 0.5 h / Ambient temperature

12: 1.) LiCl, diisopropylethylamine / 1.) CH₃CN, RT, 10 min, 2.) CH₃CN, RT, 20 h

13: (S)-2-methyl-CBS-oxazaborolidine, BF₃*THF / tetrahydrofuran; toluene / 0.08 h / 0 °C

14: p-TsOH*H₂O / benzene / 2 h / Ambient temperature

With 1H-imidazole; copper(l) iodide; n-butyllithium; boron trifluoride-tetrahydrofuran complex; 2,2'-azobis(isobutyronitrile); Na₂PO₄ buffer; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; sodium hydride; sodium hydrogencarbonate; Dess-Martin periodane; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium chloride; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; toluene; tert-butyl alcohol; benzene;
DOI:10.1021/ja973286p

Reference yield:

: 194038-96-5
(3R,6S)-3-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-pyran-2-one

: 194039-27-5
1,2-O-(S)-pivalidene-7,24,27-tri-O-benzylokadaic acid

Guidance literature:: Multi-step reaction with 14 steps

1: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 20 min, 2.) THF, hexane, -78 deg C, 40 min

2: imidazole / CH₂Cl₂ / 0.75 h

3: 1.) CuI / 1.) Et₂O, from -78 to -40 deg C, 2.) Et₂O, -78 deg C, 2.5 h

4: p-TsOH*H₂O / benzene / 11 h / Ambient temperature

5: 98 percent / TBAF / tetrahydrofuran

6: 86 percent / Dess-Martin periodinane

7: 1.) LDA / 1.) THF, hexane, -78 deg C, 20 min, 2.) THF, hexane, -78 deg C, 15 min

8: 1.) NaH

9: n-Bu₃SnH, AIBN / toluene / 2 h / 80 °C

10: 77 percent / aq. Na₂PO₄ buffer, DDQ / CH₂Cl₂; 2-methyl-propan-2-ol / 0.05 h / Irradiation

11: 90 percent / Dess-Marti periodinane, NaHCO₃ / CH₂Cl₂ / 0.5 h / Ambient temperature

12: 1.) LiCl, diisopropylethylamine / 1.) CH₃CN, RT, 10 min, 2.) CH₃CN, RT, 20 h

13: (S)-2-methyl-CBS-oxazaborolidine, BF₃*THF / tetrahydrofuran; toluene / 0.08 h / 0 °C

14: p-TsOH*H₂O / benzene / 2 h / Ambient temperature

With 1H-imidazole; copper(l) iodide; n-butyllithium; boron trifluoride-tetrahydrofuran complex; 2,2'-azobis(isobutyronitrile); Na₂PO₄ buffer; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; sodium hydride; sodium hydrogencarbonate; Dess-Martin periodane; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium chloride; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; toluene; tert-butyl alcohol; benzene;
DOI:10.1021/ja973286p