3S,4S-bis(t-butyldiphenylsilyloxymethyl)-1S-azido-2R-fluorocyclopentane

Base Information

Chemical Name:3S,4S-bis(t-butyldiphenylsilyloxymethyl)-1S-azido-2R-fluorocyclopentane
CAS No.:187877-56-1
Molecular Formula:C₃₉H₄₈FN₃O₂Si₂
Molecular Weight:665.998
Hs Code.:

Synonyms:3S,4S-bis(t-butyldiphenylsilyloxymethyl)-1S-azido-2R-fluorocyclopentane

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of 3S,4S-bis(t-butyldiphenylsilyloxymethyl)-1S-azido-2R-fluorocyclopentane

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Technology Process of 3S,4S-bis(t-butyldiphenylsilyloxymethyl)-1S-azido-2R-fluorocyclopentane

There total 6 articles about 3S,4S-bis(t-butyldiphenylsilyloxymethyl)-1S-azido-2R-fluorocyclopentane 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: 83.0%

: 187877-16-3
(1R,2R,3S,4S)-3,4-Bis-(tert-butyl-diphenyl-silanyloxymethyl)-2-fluoro-cyclopentanol

: 187877-56-1
3S,4S-bis(t-butyldiphenylsilyloxymethyl)-1S-azido-2R-fluorocyclopentane

Guidance literature:: With di-isopropyl azodicarboxylate; diphenylphosphoranyl azide; triphenylphosphine; In tetrahydrofuran; for 20h; Ambient temperature;
DOI:10.1016/S0040-4020(96)01103-9

Reference yield:

: 141389-79-9
(3S,4S)-3,4-Bis-(tert-butyl-diphenyl-silanyloxymethyl)-cyclopentanone

: 187877-56-1
3S,4S-bis(t-butyldiphenylsilyloxymethyl)-1S-azido-2R-fluorocyclopentane

Guidance literature:: Multi-step reaction with 5 steps

1: Et₃N / toluene / 0.25 h / Heating

2: 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo<2.2.2>octane bistetrafluoroborate / dimethylformamide

3: 49 percent / LS-selectride / tetrahydrofuran / -78 °C

4: 1.) benzoic acid, Ph₃P, DIAD, 2.) NaOMe / 1) THF; 2) CH₂Cl₂, MeOH

5: (PhO)2PON₃, Ph₃P, DIAD / tetrahydrofuran

With di-isopropyl azodicarboxylate; diphenyl phosphoryl azide; sodium methylate; Selectfluor; lithium tri-sec-butyl(hydrido)borate; triethylamine; triphenylphosphine; benzoic acid; In tetrahydrofuran; N,N-dimethyl-formamide; toluene;
DOI:10.1080/07328319708002956

Reference yield:

: 187876-97-7
(3S,4S)-3,4-Bis-(tert-butyl-diphenyl-silanyloxymethyl)-2-fluoro-cyclopentanone

: 187877-56-1
3S,4S-bis(t-butyldiphenylsilyloxymethyl)-1S-azido-2R-fluorocyclopentane

Guidance literature:: Multi-step reaction with 3 steps

1: 49 percent / LS-selectride / tetrahydrofuran / -78 °C

2: 1.) benzoic acid, Ph₃P, DIAD, 2.) NaOMe / 1) THF; 2) CH₂Cl₂, MeOH

3: (PhO)2PON₃, Ph₃P, DIAD / tetrahydrofuran

With di-isopropyl azodicarboxylate; diphenyl phosphoryl azide; sodium methylate; lithium tri-sec-butyl(hydrido)borate; triphenylphosphine; benzoic acid; In tetrahydrofuran;
DOI:10.1080/07328319708002956