(S)-4-[(2S,3R,6R,8S,9S)-8-((R)-4-Benzyloxy-1-methyl-butyl)-3,9-dimethyl-1,7-dioxa-spiro[5.5]undec-2-yl]-2-methyl-butyraldehyde

Base Information

Chemical Name:(S)-4-[(2S,3R,6R,8S,9S)-8-((R)-4-Benzyloxy-1-methyl-butyl)-3,9-dimethyl-1,7-dioxa-spiro[5.5]undec-2-yl]-2-methyl-butyraldehyde
CAS No.:329914-23-0
Molecular Formula:C₂₈H₄₄O₄
Molecular Weight:444.655
Hs Code.:

Synonyms:(S)-4-[(2S,3R,6R,8S,9S)-8-((R)-4-Benzyloxy-1-methyl-butyl)-3,9-dimethyl-1,7-dioxa-spiro[5.5]undec-2-yl]-2-methyl-butyraldehyde

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Chemical Property of (S)-4-[(2S,3R,6R,8S,9S)-8-((R)-4-Benzyloxy-1-methyl-butyl)-3,9-dimethyl-1,7-dioxa-spiro[5.5]undec-2-yl]-2-methyl-butyraldehyde

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Technology Process of (S)-4-[(2S,3R,6R,8S,9S)-8-((R)-4-Benzyloxy-1-methyl-butyl)-3,9-dimethyl-1,7-dioxa-spiro[5.5]undec-2-yl]-2-methyl-butyraldehyde

There total 8 articles about (S)-4-[(2S,3R,6R,8S,9S)-8-((R)-4-Benzyloxy-1-methyl-butyl)-3,9-dimethyl-1,7-dioxa-spiro[5.5]undec-2-yl]-2-methyl-butyraldehyde 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:

: 329914-11-6
(2S,5S,6R,12S,13S,14R)-2,6,12,14-tetramethyl-1-(tert-butyldimethylsilyl)oxy-5,13-(triethylsilyl)oxy-17-benzyloxy-7,10-heptadecyn-9-one

: 329914-23-0
(S)-4-[(2S,3R,6R,8S,9S)-8-((R)-4-Benzyloxy-1-methyl-butyl)-3,9-dimethyl-1,7-dioxa-spiro[5.5]undec-2-yl]-2-methyl-butyraldehyde

Guidance literature:: Multi-step reaction with 3 steps

1: 95 percent / H₂ / Pd/CaCO₃/Pb / ethyl acetate

2: 50 percent / aq. HCl / methanol / 3 h

3: Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 1 h

With hydrogenchloride; hydrogen; sodium hydrogencarbonate; Dess-Martin periodane; Lindlar's catalyst; In methanol; dichloromethane; ethyl acetate; 3: Dess-Martin oxidation;
DOI:10.1021/jo0056951

Reference yield:

: 329914-10-5
(2S,5S,6R,12S,13S,14R)-2,6,12,14-tetramethyl-1-(tert-butyldimethylsilyl)oxy-5,13-(triethylsilyl)oxy-17-benzyloxy-7,10-heptadecyn-9-ol

: 329914-23-0
(S)-4-[(2S,3R,6R,8S,9S)-8-((R)-4-Benzyloxy-1-methyl-butyl)-3,9-dimethyl-1,7-dioxa-spiro[5.5]undec-2-yl]-2-methyl-butyraldehyde

Guidance literature:: Multi-step reaction with 4 steps

1: 86 percent / tetrapropylammonium perruthenate; NMO; 4 Angstroem MS / CH₂Cl₂ / 0.5 h

2: 95 percent / H₂ / Pd/CaCO₃/Pb / ethyl acetate

3: 50 percent / aq. HCl / methanol / 3 h

4: Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 1 h

With hydrogenchloride; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 Angstroem MS; hydrogen; sodium hydrogencarbonate; Dess-Martin periodane; Lindlar's catalyst; In methanol; dichloromethane; ethyl acetate; 4: Dess-Martin oxidation;
DOI:10.1021/jo0056951

Reference yield:

: C₂₃H₃₇LiO₂Si

: 329914-23-0
(S)-4-[(2S,3R,6R,8S,9S)-8-((R)-4-Benzyloxy-1-methyl-butyl)-3,9-dimethyl-1,7-dioxa-spiro[5.5]undec-2-yl]-2-methyl-butyraldehyde

Guidance literature:: Multi-step reaction with 6 steps

1: 73 percent / tetrahydrofuran / 1 h / -78 - 0 °C

2: 96 percent / H₂ / Pd/CaCO₃/Pb / ethyl acetate / 22 h

3: 88 percent / tetrahydrofuran / 1 h / -78 - 0 °C

4: 95 percent / H₂ / Pd/CaCO₃/Pb / ethyl acetate / 26 h

5: 50 percent / aq. HCl / methanol / 3 h

6: Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 1 h

With hydrogenchloride; hydrogen; sodium hydrogencarbonate; Dess-Martin periodane; Lindlar's catalyst; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; 6: Dess-Martin oxidation;
DOI:10.1021/jo0056951