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

Base Information

• Chemical Name: (2R,5Z,8S,9R)-8-(tert-butyldiphenylsilanyloxy)-9-(tert-butyldiphenylsilanyloxymethyl)-2-vinyl-2,3,4,7,8,9-hexahydrooxonine
• CAS No.: 852213-23-1
• Molecular Formula: C₄₃H₅₄O₃Si₂
• Molecular Weight: 675.071
• Mol file: 852213-23-1.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about (2R,5Z,8S,9R)-8-(tert-butyldiphenylsilanyloxy)-9-(tert-butyldiphenylsilanyloxymethyl)-2-vinyl-2,3,4,7,8,9-hexahydrooxonine 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%

Methyltriphenylphosphonium bromide (1779-49-3) + (2R,5Z,8S,9R)-8-(tert-butyldiphenylsilanyloxy)-9-(tert-butyldiphenylsilanyloxymethyl)-2,3,4,7,8,9-hexahydrooxonine-2-carbaldehyde (749924-31-0) → (2R,5Z,8S,9R)-8-(tert-butyldiphenylsilanyloxy)-9-(tert-butyldiphenylsilanyloxymethyl)-2-vinyl-2,3,4,7,8,9-hexahydrooxonine (852213-23-1)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.333333h;

DOI:10.1039/b413426e

Reference yield: 89.0%

(2R,5Z,8S,9R)-8-(tert-butyldiphenylsilanyloxy)-9-(tert-butyldiphenylsilanyloxymethyl)-2-vinyl-2,3,4,7,8,9-hexahydrooxonine (852213-23-1) → (2R,5Z,8S,9R)-8-(tert-butyldiphenylsilanyloxy)-9-hydroxymethyl-2-vinyl-2,3,4,7,8,9-hexahydrooxonine (852213-25-3)

Guidance literature:

With pyridine; pyridine hydrogenfluoride; In tetrahydrofuran; for 16h;

DOI:10.1039/b413426e

Reference yield:

(2R,5Z,8S,9R)-8-(tert-butyldiphenylsilanyloxy)-9-(tert-butyldiphenylsilanyloxymethyl)-2-vinyl-2,3,4,7,8,9-hexahydrooxonine (852213-23-1) → (1S,2S,1'R)-[2-(tert-butyldiphenylsilanyloxy)-(bis-cyclopent-4-enyloxycyclopent-2'-enyloxy)]

Guidance literature:

Multi-step reaction with 4 steps

1: 89 percent / HF*py; pyridine / tetrahydrofuran / 16 h

2: 94 percent / o-iodoxybenzoic acid / dimethylsulfoxide / 16 h / 20 °C

3: 93 percent / n-BuLi / tetrahydrofuran / 1 h / -78 °C

4: 22 percent / [(PCy₃)2Cl₂Ru(=CHPh)] / CH₂Cl₂ / 18 h / 20 °C

With pyridine; n-butyllithium; pyridine hydrogenfluoride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; Grubbs catalyst first generation; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; 3: Wittig methylenation;

DOI:10.1039/b413426e

upstream raw materials:

Methyltriphenylphosphonium bromide

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

Downstream raw materials:

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

(1S,2S,4Z,8R,9Z)-2-(tert-butyldiphenylsilanyloxy)-11-oxabicyclo[6.2.1]undeca-4,9-diene

(1R,2S,4S,6R,9R,10Z)-2-(tert-butyldiphenylsilanyloxy)-5,12-dioxatricyclo[7.2.1.0(4,6)]-dodec-10-ene

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