(2R,5Z,8S,9R)-8-(tert-butyldiphenylsilanyloxy)-9-(tert-butyldiphenylsilanyloxymethyl)-2,3,4,7,8,9-hexahydrooxonine-2-carbaldehyde

Base Information

Chemical Name:(2R,5Z,8S,9R)-8-(tert-butyldiphenylsilanyloxy)-9-(tert-butyldiphenylsilanyloxymethyl)-2,3,4,7,8,9-hexahydrooxonine-2-carbaldehyde
CAS No.:749924-31-0
Molecular Formula:C₄₂H₅₂O₄Si₂
Molecular Weight:677.043
Hs Code.:

Synonyms:(2R,5Z,8S,9R)-8-(tert-butyldiphenylsilanyloxy)-9-(tert-butyldiphenylsilanyloxymethyl)-2,3,4,7,8,9-hexahydrooxonine-2-carbaldehyde

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Chemical Property of (2R,5Z,8S,9R)-8-(tert-butyldiphenylsilanyloxy)-9-(tert-butyldiphenylsilanyloxymethyl)-2,3,4,7,8,9-hexahydrooxonine-2-carbaldehyde

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Technology Process of (2R,5Z,8S,9R)-8-(tert-butyldiphenylsilanyloxy)-9-(tert-butyldiphenylsilanyloxymethyl)-2,3,4,7,8,9-hexahydrooxonine-2-carbaldehyde

There total 4 articles about (2R,5Z,8S,9R)-8-(tert-butyldiphenylsilanyloxy)-9-(tert-butyldiphenylsilanyloxymethyl)-2,3,4,7,8,9-hexahydrooxonine-2-carbaldehyde 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: 81.0%

: 749924-30-9
(5Z,8S,9R)-8-(tert-butyldiphenylsilanyloxy)-9-(tert-butyldiphenylsilanyloxymethyl)-2-(phenylselenylmethyl)-2,3,4,7,8,9-hexahydrooxonine

: 749924-31-0
(2R,5Z,8S,9R)-8-(tert-butyldiphenylsilanyloxy)-9-(tert-butyldiphenylsilanyloxymethyl)-2,3,4,7,8,9-hexahydrooxonine-2-carbaldehyde

Guidance literature:: (5Z,8S,9R)-8-(tert-butyldiphenylsilanyloxy)-9-(tert-butyldiphenylsilanyloxymethyl)-2-(phenylselenylmethyl)-2,3,4,7,8,9-hexahydrooxonine; With 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; at -78 ℃; for 0.416667h; Inert atmosphere;

With sodium acetate; acetic anhydride; In tetrahydrofuran; at -78 ℃; for 1.91667h; Reflux; Inert atmosphere;

With potassium carbonate; In methanol; dichloromethane; for 16h; Inert atmosphere;
DOI:10.1016/j.tetasy.2009.03.010

Reference yield:

: acetic acid [8-(tert-butyl-diphenyl-silanyloxy)-9-(tert-butyl-diphenyl-silanyloxymethyl)-2,3,4,7,8,9-hexahydro-oxonin-2-yl]-phenylselanyl-methyl ester

: 749924-31-0
(2R,5Z,8S,9R)-8-(tert-butyldiphenylsilanyloxy)-9-(tert-butyldiphenylsilanyloxymethyl)-2,3,4,7,8,9-hexahydrooxonine-2-carbaldehyde

Guidance literature:: With potassium carbonate; In methanol; dichloromethane; for 16h;
DOI:10.1055/s-2004-825627

Reference yield:

: 148903-89-3
(Z)-(8S,9R)-8-tert-butyldiphenylsilyloxy-9-tert-butyldiphenylsilyloxymethyl-2,3,4,7,8,9-hexahydro-oxonin-2-one

: 749924-31-0
(2R,5Z,8S,9R)-8-(tert-butyldiphenylsilanyloxy)-9-(tert-butyldiphenylsilanyloxymethyl)-2,3,4,7,8,9-hexahydrooxonine-2-carbaldehyde

Guidance literature:: Multi-step reaction with 4 steps

1.1: 83 percent / toluene / 0.5 h / 110 °C

2.1: tetrahydrofuran

2.2: 52 percent / LiAlH₄ / tetrahydrofuran / -78 °C

3.1: m-CPBA / tetrahydrofuran

3.2: NaOAc / tetrahydrofuran

4.1: K₂CO₃ / methanol; CH₂Cl₂ / 16 h

With potassium carbonate; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; dichloromethane; toluene; 1.1: Petasis methylenation / 3.2: Pummerer rearrangement;
DOI:10.1055/s-2004-825627