(2S,3S,6R,8S,9R)-2-((R)-4-Benzyloxy-1-methyl-butyl)-3,9-dimethyl-8-((S)-3-methyl-pent-4-enyl)-1,7-dioxa-spiro[5.5]undecane

Base Information

Chemical Name:(2S,3S,6R,8S,9R)-2-((R)-4-Benzyloxy-1-methyl-butyl)-3,9-dimethyl-8-((S)-3-methyl-pent-4-enyl)-1,7-dioxa-spiro[5.5]undecane
CAS No.:329914-24-1
Molecular Formula:C₂₉H₄₆O₃
Molecular Weight:442.682
Hs Code.:

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

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

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

There total 9 articles about (2S,3S,6R,8S,9R)-2-((R)-4-Benzyloxy-1-methyl-butyl)-3,9-dimethyl-8-((S)-3-methyl-pent-4-enyl)-1,7-dioxa-spiro[5.5]undecane 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%

: 1779-49-3
Methyltriphenylphosphonium bromide

: 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

: 329914-24-1
(2S,3S,6R,8S,9R)-2-((R)-4-Benzyloxy-1-methyl-butyl)-3,9-dimethyl-8-((S)-3-methyl-pent-4-enyl)-1,7-dioxa-spiro[5.5]undecane

Guidance literature:: With potassium tert-butylate; In tetrahydrofuran; at 0 ℃; for 1h;
DOI:10.1021/jo0056951

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

: 329914-24-1
(2S,3S,6R,8S,9R)-2-((R)-4-Benzyloxy-1-methyl-butyl)-3,9-dimethyl-8-((S)-3-methyl-pent-4-enyl)-1,7-dioxa-spiro[5.5]undecane

Guidance literature:: Multi-step reaction with 4 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

4: 90 percent / potassium t-butoxide / tetrahydrofuran / 1 h / 0 °C

With hydrogenchloride; potassium tert-butylate; hydrogen; sodium hydrogencarbonate; Dess-Martin periodane; Lindlar's catalyst; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; 3: Dess-Martin oxidation / 4: Wittig methylenation;
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

: 329914-24-1
(2S,3S,6R,8S,9R)-2-((R)-4-Benzyloxy-1-methyl-butyl)-3,9-dimethyl-8-((S)-3-methyl-pent-4-enyl)-1,7-dioxa-spiro[5.5]undecane

Guidance literature:: Multi-step reaction with 5 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

5: 90 percent / potassium t-butoxide / tetrahydrofuran / 1 h / 0 °C

With hydrogenchloride; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 Angstroem MS; potassium tert-butylate; hydrogen; sodium hydrogencarbonate; Dess-Martin periodane; Lindlar's catalyst; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; 4: Dess-Martin oxidation / 5: Wittig methylenation;
DOI:10.1021/jo0056951