(3S,4R,5S)-5-benzyloxycarbonylamino-4-tert-butoxycarbonylamino-1-cyano-3-hydroxycyclohexene

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Chemical Name:(3S,4R,5S)-5-benzyloxycarbonylamino-4-tert-butoxycarbonylamino-1-cyano-3-hydroxycyclohexene
CAS No.:927395-77-5
Molecular Formula:C₂₀H₂₅N₃O₅
Molecular Weight:387.436
Hs Code.:

Synonyms:(3S,4R,5S)-5-benzyloxycarbonylamino-4-tert-butoxycarbonylamino-1-cyano-3-hydroxycyclohexene

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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,4R,5S)-5-benzyloxycarbonylamino-4-tert-butoxycarbonylamino-1-cyano-3-hydroxycyclohexene

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Technology Process of (3S,4R,5S)-5-benzyloxycarbonylamino-4-tert-butoxycarbonylamino-1-cyano-3-hydroxycyclohexene

There total 1 articles about (3S,4R,5S)-5-benzyloxycarbonylamino-4-tert-butoxycarbonylamino-1-cyano-3-hydroxycyclohexene 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: 97.0%

: 927395-57-1
(3aR,4S,7aS)-4-benzyloxycarbonylamino-3-tert-butoxycarbonylamino-6-cyano-3a,4,5,7a-tetrahydrobenzooxazol-2-one

: 927395-77-5
(3S,4R,5S)-5-benzyloxycarbonylamino-4-tert-butoxycarbonylamino-1-cyano-3-hydroxycyclohexene

Guidance literature:: With caesium carbonate; In methanol; at 20 ℃; for 3h;
DOI:10.1021/ol062663c

Reference yield: 94.0%

: 927395-77-5
(3S,4R,5S)-5-benzyloxycarbonylamino-4-tert-butoxycarbonylamino-1-cyano-3-hydroxycyclohexene

: 927395-78-6
(4R,5S)-5-benzyloxycarbonylamino-4-tert-butoxycarbonylamino-1-cyanocyclohexen-3-one

Guidance literature:: With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 19h;
DOI:10.1021/ol062663c

Reference yield:

: 927395-77-5
(3S,4R,5S)-5-benzyloxycarbonylamino-4-tert-butoxycarbonylamino-1-cyano-3-hydroxycyclohexene

: 196618-13-0
oseltamivir

Guidance literature:: Multi-step reaction with 6 steps

1.1: 94 percent / Dess-Martin periodinane / CH₂Cl₂ / 19 h / 20 °C

2.1: 91 percent / LiAlH(O-t-Bu)3 / tetrahydrofuran / 2 h / -20 - 0 °C

3.1: 87 percent / triphenylphosphine; DEAD / tetrahydrofuran; toluene / 3 h / 0 °C

4.1: 51 percent / BF₃*OEt₂ / 5 h / -20 °C

5.1: TFA / CH₂Cl₂ / 3 h / 0 - 20 °C

5.2: 81 percent / triethylamine / CH₂Cl₂ / 16 h / 0 - 20 °C

6.1: HCl / 24 h / 20 °C

6.2: water / ethanol / 2 h / 20 °C

6.3: 74 percent / aq. ammonia / ethanol / 10 h / 20 °C

With hydrogenchloride; boron trifluoride diethyl etherate; Dess-Martin periodane; lithium tri-t-butoxyaluminum hydride; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; toluene; 3.1: Mitsunobu reaction;
DOI:10.1021/ol062663c