(-)-(1R,2S,3S,4R)-1,2,3-tris{[(tert-butyl)dimethylsilyl]oxy}-4-phthalimidocyclohex-5-ene

Base Information

Chemical Name:(-)-(1R,2S,3S,4R)-1,2,3-tris{[(tert-butyl)dimethylsilyl]oxy}-4-phthalimidocyclohex-5-ene
CAS No.:861668-42-0
Molecular Formula:C₃₂H₅₅NO₅Si₃
Molecular Weight:618.049
Hs Code.:

Synonyms:(-)-(1R,2S,3S,4R)-1,2,3-tris{[(tert-butyl)dimethylsilyl]oxy}-4-phthalimidocyclohex-5-ene

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Chemical Property of (-)-(1R,2S,3S,4R)-1,2,3-tris{[(tert-butyl)dimethylsilyl]oxy}-4-phthalimidocyclohex-5-ene

Chemical Property:

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Technology Process of (-)-(1R,2S,3S,4R)-1,2,3-tris{[(tert-butyl)dimethylsilyl]oxy}-4-phthalimidocyclohex-5-ene

There total 4 articles about (-)-(1R,2S,3S,4R)-1,2,3-tris{[(tert-butyl)dimethylsilyl]oxy}-4-phthalimidocyclohex-5-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:

: 136918-14-4,85-41-6
phthalimide

: (4R,5S,6S)-4,5,6-Tris-(tert-butyl-dimethyl-silanyloxy)-cyclohex-2-enol

: 861668-42-0
(-)-(1R,2S,3S,4R)-1,2,3-tris{[(tert-butyl)dimethylsilyl]oxy}-4-phthalimidocyclohex-5-ene

: 872976-89-1
(-)-2-((1S,4R,5S,6S)-4,5,6-tris-{[tert-butyl(dimethyl)silyl]oxy}cyclohex-2-en-1-yl)-1H-isoindole-1,3(2H)-dione

Guidance literature:: With triphenylphosphine; diethylazodicarboxylate; In toluene; at 0 ℃; for 12h;
DOI:10.1016/j.bmcl.2005.04.023

Reference yield:

: 129745-62-6
(-)-(4R,5S,6R)-4,5,6-tris(<(tert-butyl)dimethylsilyl>oxy)cyclohex-2-en-1-one

: 861668-42-0
(-)-(1R,2S,3S,4R)-1,2,3-tris{[(tert-butyl)dimethylsilyl]oxy}-4-phthalimidocyclohex-5-ene

Guidance literature:: Multi-step reaction with 2 steps

1: NaBH₄; CeCl₃*7H₂O / methanol / 0 °C

2: Ph₃P; DEAD / toluene / 12 h / 0 °C

With sodium tetrahydroborate; cerium(III) chloride; triphenylphosphine; diethylazodicarboxylate; In methanol; toluene;
DOI:10.1002/hlca.200590220

Reference yield:

: 129829-53-4
(+)-(1R,4R,5R,6R)-2,2-bis(benzyloxy)-5,6-exo-epoxy-7-oxabicyclo<2.2.1>heptane

: 861668-42-0
(-)-(1R,2S,3S,4R)-1,2,3-tris{[(tert-butyl)dimethylsilyl]oxy}-4-phthalimidocyclohex-5-ene

Guidance literature:: Multi-step reaction with 4 steps

1.1: BnOH; FSO₃H / CH₂Cl₂ / -15 °C

1.2: 92 percent / H₂ / Pd(OH)2/C

2.1: 1H-imidazole / dimethylformamide

2.2: 89 percent / Et₃N / benzene

3.1: NaBH₄; CeCl₃*7H₂O / methanol / 0 °C

4.1: Ph₃P; DEAD / toluene / 12 h / 0 °C

With 1H-imidazole; sodium tetrahydroborate; cerium(III) chloride; fluorosulphonic acid; triphenylphosphine; benzyl alcohol; diethylazodicarboxylate; In methanol; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1002/hlca.200590220