(5S,6S,8R,10S,11S)-4-benzyloxycarbonyl-5,6-diphenyloctahydro-1,7-dioxa-4-azacyclopropa[a]naphthalene

Base Information

Chemical Name:(5S,6S,8R,10S,11S)-4-benzyloxycarbonyl-5,6-diphenyloctahydro-1,7-dioxa-4-azacyclopropa[a]naphthalene
CAS No.:405144-82-3
Molecular Formula:C₂₈H₂₇NO₄
Molecular Weight:441.527
Hs Code.:

Synonyms:(5S,6S,8R,10S,11S)-4-benzyloxycarbonyl-5,6-diphenyloctahydro-1,7-dioxa-4-azacyclopropa[a]naphthalene

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Chemical Property of (5S,6S,8R,10S,11S)-4-benzyloxycarbonyl-5,6-diphenyloctahydro-1,7-dioxa-4-azacyclopropa[a]naphthalene

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Technology Process of (5S,6S,8R,10S,11S)-4-benzyloxycarbonyl-5,6-diphenyloctahydro-1,7-dioxa-4-azacyclopropa[a]naphthalene

There total 7 articles about (5S,6S,8R,10S,11S)-4-benzyloxycarbonyl-5,6-diphenyloctahydro-1,7-dioxa-4-azacyclopropa[a]naphthalene 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: 88.0%

: 405144-81-2
(2S,3S,9R,10S)-4-benzyloxycarbonyl-2,3-diphenyl-2,3;5,6;9,10-hexahydrobenzo-1,4-oxazine

: 405144-82-3
(5S,6S,8R,10S,11S)-4-benzyloxycarbonyl-5,6-diphenyloctahydro-1,7-dioxa-4-azacyclopropa[a]naphthalene

Guidance literature:: With 3,3-dimethyldioxirane; In acetone; at 0 ℃; for 5h;
DOI:10.1016/S0957-4166(01)00484-0

Reference yield:

: 530-36-9,3764-63-4,13286-63-0,23190-16-1,23190-17-2,23364-44-5,23412-95-5,39664-87-4,88082-66-0
(1S,2S)-2-amino-1,2-diphenylethanol

: 405144-82-3
(5S,6S,8R,10S,11S)-4-benzyloxycarbonyl-5,6-diphenyloctahydro-1,7-dioxa-4-azacyclopropa[a]naphthalene

Guidance literature:: Multi-step reaction with 5 steps

1: 95 percent / PPh₃; Et₃N / Pd(PPh₃)4 / tetrahydrofuran / 5 h / 45 - 50 °C

2: 2.83 g / tetrahydrofuran; CH₂Cl₂ / 3 h / -78 °C

3: 98 percent / NaH / tetrahydrofuran / 1.5 h / 0 - 20 °C

4: 91 percent / NaIO₄; NaHCO₃ / methanol; H₂O / 48 h / 20 - 70 °C

5: 88 percent / dimethyldioxirane / acetone / 5 h / 0 °C

With sodium periodate; 3,3-dimethyldioxirane; sodium hydride; sodium hydrogencarbonate; triethylamine; triphenylphosphine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; dichloromethane; water; acetone;
DOI:10.1016/S0957-4166(01)00484-0

Reference yield:

: 1521-51-3,113667-32-6
rac-3-bromocyclohexene

: 405144-82-3
(5S,6S,8R,10S,11S)-4-benzyloxycarbonyl-5,6-diphenyloctahydro-1,7-dioxa-4-azacyclopropa[a]naphthalene

Guidance literature:: Multi-step reaction with 5 steps

1: 95 percent / PPh₃; Et₃N / Pd(PPh₃)4 / tetrahydrofuran / 5 h / 45 - 50 °C

2: 2.83 g / tetrahydrofuran; CH₂Cl₂ / 3 h / -78 °C

3: 98 percent / NaH / tetrahydrofuran / 1.5 h / 0 - 20 °C

4: 91 percent / NaIO₄; NaHCO₃ / methanol; H₂O / 48 h / 20 - 70 °C

5: 88 percent / dimethyldioxirane / acetone / 5 h / 0 °C

With sodium periodate; 3,3-dimethyldioxirane; sodium hydride; sodium hydrogencarbonate; triethylamine; triphenylphosphine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; dichloromethane; water; acetone;
DOI:10.1016/S0957-4166(01)00484-0