(2R,3R,4S,5S,6R)-1-[(tert-butyldiphenylsilyl)oxy]-2,4,6-trimethyl-3,5-dihydroxyoct-7-ene

Base Information

• Chemical Name: (2R,3R,4S,5S,6R)-1-[(tert-butyldiphenylsilyl)oxy]-2,4,6-trimethyl-3,5-dihydroxyoct-7-ene
• CAS No.: 209250-96-4
• Molecular Formula: C₂₇H₄₀O₃Si
• Molecular Weight: 440.698
• Mol file: 209250-96-4.mol

Synonyms:(2R,3R,4S,5S,6R)-1-[(tert-butyldiphenylsilyl)oxy]-2,4,6-trimethyl-3,5-dihydroxyoct-7-ene

Chemical Property of (2R,3R,4S,5S,6R)-1-[(tert-butyldiphenylsilyl)oxy]-2,4,6-trimethyl-3,5-dihydroxyoct-7-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4S,5S,6R)-1-[(tert-butyldiphenylsilyl)oxy]-2,4,6-trimethyl-3,5-dihydroxyoct-7-ene

There total 9 articles about (2R,3R,4S,5S,6R)-1-[(tert-butyldiphenylsilyl)oxy]-2,4,6-trimethyl-3,5-dihydroxyoct-7-ene 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: 64.0%

(2R,3R,4S,5S,6R)-1-[(tert-butyldiphenylsilyl)oxy]-5-hydroxy-3-[(para-methoxybenzyl)oxy]-2,4,6-trimethyloct-7-ene (235785-59-8) → (2R,3R,4S,5S,6R)-1-[(tert-butyldiphenylsilyl)oxy]-2,4,6-trimethyl-3,5-dihydroxyoct-7-ene (209250-96-4)

Guidance literature:

(2R,3R,4S,5S,6R)-1-[(tert-butyldiphenylsilyl)oxy]-5-hydroxy-3-[(para-methoxybenzyl)oxy]-2,4,6-trimethyloct-7-ene; With dmap; acetic anhydride; triethylamine; In dichloromethane; at 23 ℃; for 12h;

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In phosphate buffer; dichloromethane; at 23 ℃; for 1h; pH=7;

With potassium carbonate; In methanol; for 2h; Further stages.;

DOI:10.1021/jo0267908

Reference yield:

(Z)-crotyltrifluorosilane (51676-18-7) + (2R,3R,4R)-5-(tert-Butyl-diphenyl-silanyloxy)-3-hydroxy-2,4-dimethyl-pentanal (209250-90-8) → (2R,3R,4S,5S,6R)-1-[(tert-butyldiphenylsilyl)oxy]-2,4,6-trimethyl-3,5-dihydroxyoct-7-ene (209250-96-4) + (2R,3R,4S,5S,6S)-1-[(tert-butyldiphenylsilyl)oxy]-2,4,6-trimethyl-3,5-dihydroxyoct-7-ene (209250-95-3)

Guidance literature:

With hydrogenchloride; sodium hydroxide; N-ethyl-N,N-diisopropylamine; Yield given. Multistep reaction. Yields of byproduct given; 1.) CH₂Cl₂, 0 deg C, 36 h, 2.) 15 min, 3.) THF, 1 h;

DOI:10.1021/jo980387c

Reference yield:

((E)-2-butenyl)trifluorosilane (114067-35-5) + (2R,3R,4R)-5-(tert-Butyl-diphenyl-silanyloxy)-3-hydroxy-2,4-dimethyl-pentanal (209250-90-8) → (2R,3R,4S,5S,6R)-1-[(tert-butyldiphenylsilyl)oxy]-2,4,6-trimethyl-3,5-dihydroxyoct-7-ene (209250-96-4) + (2R,3R,4S,5R,6R)-1-(tert-Butyl-diphenyl-silanyloxy)-2,4,6-trimethyl-oct-7-ene-3,5-diol

Guidance literature:

With 4 A molecular sieve; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃; for 36h;

DOI:10.1016/S0040-4039(99)00730-3

upstream raw materials:

(Z)-crotyltrifluorosilane

(2R,3R,4R)-5-(tert-Butyl-diphenyl-silanyloxy)-3-hydroxy-2,4-dimethyl-pentanal

((E)-2-butenyl)trifluorosilane

(2R,3R,4S,5S,6R)-1-[(tert-butyldiphenylsilyl)oxy]-5-hydroxy-3-[(para-methoxybenzyl)oxy]-2,4,6-trimethyloct-7-ene