methyl (1aS,8R,9S,9aS)-1,1a,2,8,9,9a-hexahydro-7-(benzyloxy)-8-{[(benzyloxycarbonyl)oxy]methyl}-1-(tert-butyloxycarbonyl)-8-formyl-9-hydroxy-3,9-epoxy-3H-azirino[2,3-c][1]benzazocin-5-carboxylate

Base Information

Chemical Name:methyl (1aS,8R,9S,9aS)-1,1a,2,8,9,9a-hexahydro-7-(benzyloxy)-8-{[(benzyloxycarbonyl)oxy]methyl}-1-(tert-butyloxycarbonyl)-8-formyl-9-hydroxy-3,9-epoxy-3H-azirino[2,3-c][1]benzazocin-5-carboxylate
CAS No.:187682-52-6
Molecular Formula:C₃₅H₃₆N₂O₁₁
Molecular Weight:660.678
Hs Code.:

methyl (1aS,8R,9S,9aS)-1,1a,2,8,9,9a-hexahydro-7-(benzyloxy)-8-{[(benzyloxycarbonyl)oxy]methyl}-1-(tert-butyloxycarbonyl)-8-formyl-9-hydroxy-3,9-epoxy-3H-azirino[2,3-c][1]benzazocin-5-carboxylate

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Chemical Property of methyl (1aS,8R,9S,9aS)-1,1a,2,8,9,9a-hexahydro-7-(benzyloxy)-8-{[(benzyloxycarbonyl)oxy]methyl}-1-(tert-butyloxycarbonyl)-8-formyl-9-hydroxy-3,9-epoxy-3H-azirino[2,3-c][1]benzazocin-5-carboxylate

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Technology Process of methyl (1aS,8R,9S,9aS)-1,1a,2,8,9,9a-hexahydro-7-(benzyloxy)-8-{[(benzyloxycarbonyl)oxy]methyl}-1-(tert-butyloxycarbonyl)-8-formyl-9-hydroxy-3,9-epoxy-3H-azirino[2,3-c][1]benzazocin-5-carboxylate

There total 7 articles about methyl (1aS,8R,9S,9aS)-1,1a,2,8,9,9a-hexahydro-7-(benzyloxy)-8-{[(benzyloxycarbonyl)oxy]methyl}-1-(tert-butyloxycarbonyl)-8-formyl-9-hydroxy-3,9-epoxy-3H-azirino[2,3-c][1]benzazocin-5-carboxylate 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:

: 187682-40-2
C₂₆H₂₈N₂O₆

: 187682-52-6
methyl (1aS,8R,9S,9aS)-1,1a,2,8,9,9a-hexahydro-7-(benzyloxy)-8-{[(benzyloxycarbonyl)oxy]methyl}-1-(tert-butyloxycarbonyl)-8-formyl-9-hydroxy-3,9-epoxy-3H-azirino[2,3-c][1]benzazocin-5-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1: NaHCO₃ / CH₂Cl₂; methanol; H₂O / 2 h / Ambient temperature

2: acetonitrile / 3.5 h / Ambient temperature

3: DMAP / acetonitrile / 3 h / 63 °C

4: 98 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 2 h / 0 °C

5: 1.) acetic anhydride, 2.) m-chloroperbenzoic acid / 1) THF, 0 deg C, 24 h; 2) CH₂Cl₂, 0 deg C, 1.5 h

With dmap; acetic anhydride; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In methanol; dichloromethane; water; acetonitrile;
DOI:10.1021/jo961992n

Reference yield:

: 187682-39-9
methyl (1aS,8R,8aS,8bR)-1,1a,2,8,8a,8b-hexahydro-7-(benzyloxy)-1-(tert-butyloxycarbonyl)-8-formyl-8-(hydroxymethyl)azirino[2',3':3,4]pyrrolo[1,2-a]indole-5-carboxylate

: 187682-52-6
methyl (1aS,8R,9S,9aS)-1,1a,2,8,9,9a-hexahydro-7-(benzyloxy)-8-{[(benzyloxycarbonyl)oxy]methyl}-1-(tert-butyloxycarbonyl)-8-formyl-9-hydroxy-3,9-epoxy-3H-azirino[2,3-c][1]benzazocin-5-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1: acetonitrile / 3.5 h / Ambient temperature

2: DMAP / acetonitrile / 3 h / 63 °C

3: 98 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 2 h / 0 °C

4: 1.) acetic anhydride, 2.) m-chloroperbenzoic acid / 1) THF, 0 deg C, 24 h; 2) CH₂Cl₂, 0 deg C, 1.5 h

With dmap; acetic anhydride; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; acetonitrile;
DOI:10.1021/jo961992n

Reference yield:

: 187682-48-0
methyl (1aS,8R,8aS,8bR)-1,1a,2,8,8a,8b-hexahydro-7-(benzyloxy)-8-{[(benzyloxycarbonyl)oxy]methyl}-1-(tert-butyloxycarbonyl)-8-formylazirino[2',3':3,4]pyrrolo[1,2-a]indole-5-carboxylate

: 187682-52-6
methyl (1aS,8R,9S,9aS)-1,1a,2,8,9,9a-hexahydro-7-(benzyloxy)-8-{[(benzyloxycarbonyl)oxy]methyl}-1-(tert-butyloxycarbonyl)-8-formyl-9-hydroxy-3,9-epoxy-3H-azirino[2,3-c][1]benzazocin-5-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: 98 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 2 h / 0 °C

2: 1.) acetic anhydride, 2.) m-chloroperbenzoic acid / 1) THF, 0 deg C, 24 h; 2) CH₂Cl₂, 0 deg C, 1.5 h

With acetic anhydride; 3-chloro-benzenecarboperoxoic acid; In dichloromethane;
DOI:10.1021/jo961992n