(3S,4S)-O-(4-tert-butoxycarbonylamino-5-tert-butyldiphenylsilyloxy-3-fluoromethylpentyl)-1H-imidazole-1-carbothioate

Base Information

Chemical Name:(3S,4S)-O-(4-tert-butoxycarbonylamino-5-tert-butyldiphenylsilyloxy-3-fluoromethylpentyl)-1H-imidazole-1-carbothioate
CAS No.:691407-34-8
Molecular Formula:C₃₁H₄₂FN₃O₄SSi
Molecular Weight:599.842
Hs Code.:

Synonyms:(3S,4S)-O-(4-tert-butoxycarbonylamino-5-tert-butyldiphenylsilyloxy-3-fluoromethylpentyl)-1H-imidazole-1-carbothioate

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Chemical Property of (3S,4S)-O-(4-tert-butoxycarbonylamino-5-tert-butyldiphenylsilyloxy-3-fluoromethylpentyl)-1H-imidazole-1-carbothioate

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Technology Process of (3S,4S)-O-(4-tert-butoxycarbonylamino-5-tert-butyldiphenylsilyloxy-3-fluoromethylpentyl)-1H-imidazole-1-carbothioate

There total 8 articles about (3S,4S)-O-(4-tert-butoxycarbonylamino-5-tert-butyldiphenylsilyloxy-3-fluoromethylpentyl)-1H-imidazole-1-carbothioate 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: 100.0%

: 6160-65-2
1,1'-Thiocarbonyldiimidazole

: 691407-33-7
(2S,3S)-2-N-tert-butoxycarbonylamino-1-tert-butyldiphenylsilyloxy-3-fluoromethyl-5-hydroxypentane

: 691407-34-8
(3S,4S)-O-(4-tert-butoxycarbonylamino-5-tert-butyldiphenylsilyloxy-3-fluoromethylpentyl)-1H-imidazole-1-carbothioate

Guidance literature:: In dichloromethane; at 20 ℃; for 12h;
DOI:10.1039/b316219b

Reference yield:

: 138871-58-6
(S)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-oxo-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester

: 691407-34-8
(3S,4S)-O-(4-tert-butoxycarbonylamino-5-tert-butyldiphenylsilyloxy-3-fluoromethylpentyl)-1H-imidazole-1-carbothioate

Guidance literature:: Multi-step reaction with 6 steps

1: 68 percent / benzophenone / 24 h / 20 °C / Irradiation

2: 61 percent / Et₂NSF₃ / CH₂Cl₂ / 2 h / 20 °C

3: 100 percent / aq. LiOH / tetrahydrofuran / 3 h / 0 - 20 °C

4: Et₃N / tetrahydrofuran / 1 h / -40 °C

5: 2.99 g / NaBH₄ / tetrahydrofuran; H₂O / 1 h / 0 °C

6: 100 percent / CH₂Cl₂ / 12 h / 20 °C

With lithium hydroxide; sodium tetrahydroborate; benzophenone; diethylamino-sulfur trifluoride; triethylamine; In tetrahydrofuran; dichloromethane; water;
DOI:10.1039/b316219b

Reference yield:

: 691407-26-8
(4S,5S)-N-tert-butoxycarbonyl-5-tert-butyldiphenylsilyloxymethyl-2-oxopyrrolidine-4-carbaldehyde

: 691407-34-8
(3S,4S)-O-(4-tert-butoxycarbonylamino-5-tert-butyldiphenylsilyloxy-3-fluoromethylpentyl)-1H-imidazole-1-carbothioate

Guidance literature:: Multi-step reaction with 6 steps

1: 75 percent / NaBH₄ / methanol / 0.42 h / 20 °C

2: 61 percent / Et₂NSF₃ / CH₂Cl₂ / 2 h / 20 °C

3: 100 percent / aq. LiOH / tetrahydrofuran / 3 h / 0 - 20 °C

4: Et₃N / tetrahydrofuran / 1 h / -40 °C

5: 2.99 g / NaBH₄ / tetrahydrofuran; H₂O / 1 h / 0 °C

6: 100 percent / CH₂Cl₂ / 12 h / 20 °C

With lithium hydroxide; sodium tetrahydroborate; diethylamino-sulfur trifluoride; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water;
DOI:10.1039/b316219b