(1R,2S,4R,5S,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-cyano-4-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-oxa-bicyclo[3.1.0]hexane-6-carboxylic acid

Base Information

Chemical Name:(1R,2S,4R,5S,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-cyano-4-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-oxa-bicyclo[3.1.0]hexane-6-carboxylic acid
CAS No.:190723-60-5
Molecular Formula:C₂₈H₂₉N₃O₆Si
Molecular Weight:531.64
Hs Code.:

(1R,2S,4R,5S,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-cyano-4-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-oxa-bicyclo[3.1.0]hexane-6-carboxylic acid

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Chemical Property of (1R,2S,4R,5S,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-cyano-4-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-oxa-bicyclo[3.1.0]hexane-6-carboxylic acid

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Technology Process of (1R,2S,4R,5S,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-cyano-4-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-oxa-bicyclo[3.1.0]hexane-6-carboxylic acid

There total 9 articles about (1R,2S,4R,5S,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-cyano-4-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-oxa-bicyclo[3.1.0]hexane-6-carboxylic acid 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:

: 190723-59-2
(1R,2S,4R,5S,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-cyano-4-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-oxa-bicyclo[3.1.0]hexane-6-carboxylic acid benzyl ester

: 190723-60-5
(1R,2S,4R,5S,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-cyano-4-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-oxa-bicyclo[3.1.0]hexane-6-carboxylic acid

Guidance literature:: With hydrogen; palladium on activated charcoal; In methanol; for 4h; Yield given; Ambient temperature;
DOI:10.1055/s-1997-802

Reference yield:

: 130351-69-8
1-<5-O-(tert-butyldiphenylsilyl)-2,3-epoxy-β-D-lyxo-pentofuranosyl>uracil

: 190723-60-5
(1R,2S,4R,5S,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-cyano-4-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-oxa-bicyclo[3.1.0]hexane-6-carboxylic acid

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) LAH; 2.) pyridine / 1.) THF, 0 deg C, 30 min; 2.) 0 deg C to rt., 24 h

2: t-BuOK / dimethylformamide / 0.12 h / 0 °C

3: 84 percent / m-chloroperbenzoic acid / methanol / 12 h / 0 - 25 °C

4: 84 percent / t-BuOK / tetrahydrofuran / 0 - 25 °C

5: H₂ / Pd/C / methanol / 4 h / Ambient temperature

With pyridine; lithium aluminium tetrahydride; potassium tert-butylate; hydrogen; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;
DOI:10.1055/s-1997-802

Reference yield:

: 130351-68-7
1-(5-O-tert-butyldiphenylsilyl-β-D-ribofuranosyl)uracil

: 190723-60-5
(1R,2S,4R,5S,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-cyano-4-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-oxa-bicyclo[3.1.0]hexane-6-carboxylic acid

Guidance literature:: Multi-step reaction with 7 steps

1: pyridine / 2 h / 0 °C

2: 1N NaOH / 3 h / Ambient temperature

3: 1.) LAH; 2.) pyridine / 1.) THF, 0 deg C, 30 min; 2.) 0 deg C to rt., 24 h

4: t-BuOK / dimethylformamide / 0.12 h / 0 °C

5: 84 percent / m-chloroperbenzoic acid / methanol / 12 h / 0 - 25 °C

6: 84 percent / t-BuOK / tetrahydrofuran / 0 - 25 °C

7: H₂ / Pd/C / methanol / 4 h / Ambient temperature

With pyridine; sodium hydroxide; lithium aluminium tetrahydride; potassium tert-butylate; hydrogen; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;
DOI:10.1055/s-1997-802