(R)-5-(tert-Butyl-diphenyl-silanyloxy)-6-((S)-5-methyl-2-oxo-2,5-dihydro-furan-3-yl)-hexanal

Base Information

Chemical Name:(R)-5-(tert-Butyl-diphenyl-silanyloxy)-6-((S)-5-methyl-2-oxo-2,5-dihydro-furan-3-yl)-hexanal
CAS No.:197968-28-8
Molecular Formula:C₂₇H₃₄O₄Si
Molecular Weight:450.65
Hs Code.:

Synonyms:(R)-5-(tert-Butyl-diphenyl-silanyloxy)-6-((S)-5-methyl-2-oxo-2,5-dihydro-furan-3-yl)-hexanal

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Chemical Property of (R)-5-(tert-Butyl-diphenyl-silanyloxy)-6-((S)-5-methyl-2-oxo-2,5-dihydro-furan-3-yl)-hexanal

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Technology Process of (R)-5-(tert-Butyl-diphenyl-silanyloxy)-6-((S)-5-methyl-2-oxo-2,5-dihydro-furan-3-yl)-hexanal

There total 10 articles about (R)-5-(tert-Butyl-diphenyl-silanyloxy)-6-((S)-5-methyl-2-oxo-2,5-dihydro-furan-3-yl)-hexanal 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%

: 197968-27-7
(S)-3-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-6-hydroxy-hexyl]-5-methyl-5H-furan-2-one

: 197968-28-8
(R)-5-(tert-Butyl-diphenyl-silanyloxy)-6-((S)-5-methyl-2-oxo-2,5-dihydro-furan-3-yl)-hexanal

Guidance literature:: With Celite; pyridinium chlorochromate; In dichloromethane; for 2h; Ambient temperature;
DOI:10.1021/ja981302s

Reference yield:

: (S)-3-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-hex-5-enyl]-5-methyl-5H-furan-2-one

: 197968-28-8
(R)-5-(tert-Butyl-diphenyl-silanyloxy)-6-((S)-5-methyl-2-oxo-2,5-dihydro-furan-3-yl)-hexanal

Guidance literature:: Multi-step reaction with 2 steps

1: 1.) 9-BBN₄, 2.) aq. H₂O₂, 1 N aq. NaOH / 1.) THF, 0 deg C, overnight, 2.) THF, RT, 2 h

2: 90 percent / PCC, Celite / CH₂Cl₂ / 2 h / Ambient temperature

With sodium hydroxide; Celite; dihydrogen peroxide; pyridinium chlorochromate; In dichloromethane;
DOI:10.1021/ja981302s

Reference yield:

: 18922-04-8
6-iodohex-1-ene

: 197968-28-8
(R)-5-(tert-Butyl-diphenyl-silanyloxy)-6-((S)-5-methyl-2-oxo-2,5-dihydro-furan-3-yl)-hexanal

Guidance literature:: Multi-step reaction with 9 steps

1: 72 percent

2: 62 percent / AD-mix-β

3: 1.) CH(OME)3, PPTS, 2.) AcBr, 3.) K₂CO₃

4: BF₃*Et₂O

5: DMAP

6: PPTS / ethanol

7: 1.) Red-Al, 2.) I₂, 3.) (Ph₃P)2PdCl₂, NH₂NH₂, K₂CO₃

8: CAN / H₂O; acetonitrile

9: 1.) oxalyl chloride, DMSO, 2.) Et₃N

With dmap; bis-triphenylphosphine-palladium(II) chloride; oxalyl dichloride; ammonium cerium(IV) nitrate; Acetyl bromide; AD-mix-β; boron trifluoride diethyl etherate; iodine; pyridinium p-toluenesulfonate; potassium carbonate; dimethyl sulfoxide; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; hydrazine; trimethyl orthoformate; In ethanol; water; acetonitrile;
DOI:10.1021/ja953781q