(S)-2-[(2S,6R,8S,11R)-11-Benzyloxy-8-((2S,4R)-2-tert-butyl-4-methyl-5-oxo-[1,3]dioxolan-4-ylmethyl)-4-methyl-1,7-dioxa-spiro[5.5]undec-4-en-2-yl]-propionaldehyde

Base Information Edit

Chemical Name:(S)-2-[(2S,6R,8S,11R)-11-Benzyloxy-8-((2S,4R)-2-tert-butyl-4-methyl-5-oxo-[1,3]dioxolan-4-ylmethyl)-4-methyl-1,7-dioxa-spiro[5.5]undec-4-en-2-yl]-propionaldehyde
CAS No.:194039-05-9
Molecular Formula:C₂₉H₄₀O₇
Molecular Weight:500.632
Hs Code.:
Mol file:194039-05-9.mol

(S)-2-[(2S,6R,8S,11R)-11-Benzyloxy-8-((2S,4R)-2-tert-butyl-4-methyl-5-oxo-[1,3]dioxolan-4-ylmethyl)-4-methyl-1,7-dioxa-spiro[5.5]undec-4-en-2-yl]-propionaldehyde

Synonyms:(S)-2-[(2S,6R,8S,11R)-11-Benzyloxy-8-((2S,4R)-2-tert-butyl-4-methyl-5-oxo-[1,3]dioxolan-4-ylmethyl)-4-methyl-1,7-dioxa-spiro[5.5]undec-4-en-2-yl]-propionaldehyde

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Chemical Property of (S)-2-[(2S,6R,8S,11R)-11-Benzyloxy-8-((2S,4R)-2-tert-butyl-4-methyl-5-oxo-[1,3]dioxolan-4-ylmethyl)-4-methyl-1,7-dioxa-spiro[5.5]undec-4-en-2-yl]-propionaldehyde Edit

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MSDS Files:: SDS file from LookChem

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Technology Process of (S)-2-[(2S,6R,8S,11R)-11-Benzyloxy-8-((2S,4R)-2-tert-butyl-4-methyl-5-oxo-[1,3]dioxolan-4-ylmethyl)-4-methyl-1,7-dioxa-spiro[5.5]undec-4-en-2-yl]-propionaldehyde

There total 22 articles about (S)-2-[(2S,6R,8S,11R)-11-Benzyloxy-8-((2S,4R)-2-tert-butyl-4-methyl-5-oxo-[1,3]dioxolan-4-ylmethyl)-4-methyl-1,7-dioxa-spiro[5.5]undec-4-en-2-yl]-propionaldehyde 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: 90.0%

: 203926-68-5
(2S,5R)-5-[(2S,5R,6R,8S)-5-Benzyloxy-8-((R)-2-hydroxy-1-methyl-ethyl)-10-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-ylmethyl]-2-tert-butyl-5-methyl-[1,3]dioxolan-4-one

: 194039-05-9
(S)-2-[(2S,6R,8S,11R)-11-Benzyloxy-8-((2S,4R)-2-tert-butyl-4-methyl-5-oxo-[1,3]dioxolan-4-ylmethyl)-4-methyl-1,7-dioxa-spiro[5.5]undec-4-en-2-yl]-propionaldehyde

Guidance literature:: With Dess-Martin periodane;
DOI:10.1021/ja9715206

Reference yield:

: 203926-64-1
(2S,5R,6S,8S)-5-Benzyloxy-8-[(R)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-10-methyl-1,7-dioxa-spiro[5.5]undec-10-ene-2-carbaldehyde

: 194039-05-9
(S)-2-[(2S,6R,8S,11R)-11-Benzyloxy-8-((2S,4R)-2-tert-butyl-4-methyl-5-oxo-[1,3]dioxolan-4-ylmethyl)-4-methyl-1,7-dioxa-spiro[5.5]undec-4-en-2-yl]-propionaldehyde

Guidance literature:: Multi-step reaction with 5 steps

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

2: 1.) NaH

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

4: 77 percent / aq. Na₂PO₄ buffer, DDQ / CH₂Cl₂; 2-methyl-propan-2-ol / 0.05 h / Irradiation

5: 90 percent / Dess-Marti periodinane, NaHCO₃ / CH₂Cl₂ / 0.5 h / Ambient temperature

With 2,2'-azobis(isobutyronitrile); Na₂PO₄ buffer; tri-n-butyl-tin hydride; sodium hydride; sodium hydrogencarbonate; Dess-Martin periodane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium diisopropyl amide; In dichloromethane; toluene; tert-butyl alcohol;
DOI:10.1021/ja973286p

Reference yield:

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

: 194039-05-9
(S)-2-[(2S,6R,8S,11R)-11-Benzyloxy-8-((2S,4R)-2-tert-butyl-4-methyl-5-oxo-[1,3]dioxolan-4-ylmethyl)-4-methyl-1,7-dioxa-spiro[5.5]undec-4-en-2-yl]-propionaldehyde

Guidance literature:: Multi-step reaction with 11 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

With 1H-imidazole; copper(l) iodide; n-butyllithium; 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; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; toluene; tert-butyl alcohol; benzene;
DOI:10.1021/ja973286p