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

Base Information

Chemical Name:(3aR,4S,7aS)-4-benzyloxycarbonylamino-3-tert-butoxycarbonylamino-6-cyano-3a,4,5,7a-tetrahydrobenzooxazol-2-one
CAS No.:927395-57-1
Molecular Formula:C₂₁H₂₃N₃O₆
Molecular Weight:413.43
Hs Code.:

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

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Chemical Property of (3aR,4S,7aS)-4-benzyloxycarbonylamino-3-tert-butoxycarbonylamino-6-cyano-3a,4,5,7a-tetrahydrobenzooxazol-2-one

Chemical Property:

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Technology Process of (3aR,4S,7aS)-4-benzyloxycarbonylamino-3-tert-butoxycarbonylamino-6-cyano-3a,4,5,7a-tetrahydrobenzooxazol-2-one

There total 1 articles about (3aR,4S,7aS)-4-benzyloxycarbonylamino-3-tert-butoxycarbonylamino-6-cyano-3a,4,5,7a-tetrahydrobenzooxazol-2-one 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:

: 927395-76-4
(6-cyano-2-oxo-2,3,3a,4,5,7a-hexahydro-benzooxazol-4-yl)-carbamic acid benzyl ester

: 24424-99-5
di-tert-butyl dicarbonate

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

: C₂₆H₃₁N₃O₈

Guidance literature:: With pyridine; dmap; at 20 ℃; for 10h;
DOI:10.1021/ol062663c

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:

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

: 196618-13-0
oseltamivir

Guidance literature:: Multi-step reaction with 7 steps

1.1: 97 percent / cesium carbonate / methanol / 3 h / 20 °C

2.1: 94 percent / Dess-Martin periodinane / CH₂Cl₂ / 19 h / 20 °C

3.1: 91 percent / LiAlH(O-t-Bu)3 / tetrahydrofuran / 2 h / -20 - 0 °C

4.1: 87 percent / triphenylphosphine; DEAD / tetrahydrofuran; toluene / 3 h / 0 °C

5.1: 51 percent / BF₃*OEt₂ / 5 h / -20 °C

6.1: TFA / CH₂Cl₂ / 3 h / 0 - 20 °C

6.2: 81 percent / triethylamine / CH₂Cl₂ / 16 h / 0 - 20 °C

7.1: HCl / 24 h / 20 °C

7.2: water / ethanol / 2 h / 20 °C

7.3: 74 percent / aq. ammonia / ethanol / 10 h / 20 °C

With hydrogenchloride; boron trifluoride diethyl etherate; caesium carbonate; Dess-Martin periodane; lithium tri-t-butoxyaluminum hydride; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; toluene; 4.1: Mitsunobu reaction;
DOI:10.1021/ol062663c