(1R,4S,5R,6R)-4-<(benzyloxycarbonyl)amino>-5-<(tert-butyldimethylsilyl)oxy>-9-methyl-8-oxo-9-aza-7-oxabicyclo<4.3.0>non-2-ene

Base Information

Chemical Name:(1R,4S,5R,6R)-4-<(benzyloxycarbonyl)amino>-5-<(tert-butyldimethylsilyl)oxy>-9-methyl-8-oxo-9-aza-7-oxabicyclo<4.3.0>non-2-ene
CAS No.:111515-83-4
Molecular Formula:C₂₂H₃₂N₂O₅Si
Molecular Weight:432.592
Hs Code.:

Synonyms:(1R,4S,5R,6R)-4-<(benzyloxycarbonyl)amino>-5-<(tert-butyldimethylsilyl)oxy>-9-methyl-8-oxo-9-aza-7-oxabicyclo<4.3.0>non-2-ene

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Chemical Property of (1R,4S,5R,6R)-4-<(benzyloxycarbonyl)amino>-5-<(tert-butyldimethylsilyl)oxy>-9-methyl-8-oxo-9-aza-7-oxabicyclo<4.3.0>non-2-ene

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Technology Process of (1R,4S,5R,6R)-4-<(benzyloxycarbonyl)amino>-5-<(tert-butyldimethylsilyl)oxy>-9-methyl-8-oxo-9-aza-7-oxabicyclo<4.3.0>non-2-ene

There total 18 articles about (1R,4S,5R,6R)-4-<(benzyloxycarbonyl)amino>-5-<(tert-butyldimethylsilyl)oxy>-9-methyl-8-oxo-9-aza-7-oxabicyclo<4.3.0>non-2-ene 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: 72.0%

: 124287-87-2
(1R,4S,5R,6R)-4-<(benzyloxycarbonyl)amino>-2-bromo-5-<(tert-butyldimethylsilyl)oxy>-9-methyl-8-oxo-9-aza-7-oxabicyclo<4.3.0>nonane

: 111515-83-4
(1R,4S,5R,6R)-4-<(benzyloxycarbonyl)amino>-5-<(tert-butyldimethylsilyl)oxy>-9-methyl-8-oxo-9-aza-7-oxabicyclo<4.3.0>non-2-ene

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene; for 12h; Heating;
DOI:10.1021/jo00291a014

Reference yield:

: 111515-80-1
methyl (1R,2R,4S,5R,6R)-4-azido-5-hydroxy-9-methyl-8-oxo-9-aza-7-oxabicyclo<4.3.0>nonanecarboxylate

: 111515-83-4
(1R,4S,5R,6R)-4-<(benzyloxycarbonyl)amino>-5-<(tert-butyldimethylsilyl)oxy>-9-methyl-8-oxo-9-aza-7-oxabicyclo<4.3.0>non-2-ene

Guidance literature:: Multi-step reaction with 5 steps

1: H₂ / Pd/C

2: NaHCO₃

3: 92 percent / imidazole

4: NaOH

5: 1.) 1-oxa-2-oxo-3-thia-indolizinium chloride, DMAP, CBrCl₃, 2.) DBU

With 1H-imidazole; dmap; sodium hydroxide; Bromotrichloromethane; 1-oxa-2-oxo-3-thiaindolizinium chloride; hydrogen; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; palladium on activated charcoal;
DOI:10.1246/cl.1987.29

Reference yield:

: 124287-84-9
(1R,6S)-6-<(methoxycarbonyl)amino>cyclohex-3-enecarboxylic acid

: 111515-83-4
(1R,4S,5R,6R)-4-<(benzyloxycarbonyl)amino>-5-<(tert-butyldimethylsilyl)oxy>-9-methyl-8-oxo-9-aza-7-oxabicyclo<4.3.0>non-2-ene

Guidance literature:: Multi-step reaction with 12 steps

1: 1.) I₂, KI, NaHCO₃, 2.) DBU

2: 95 percent / Ag₂O

4: triethylamine

5: 95 percent / 1,2-dichloro-ethane / Heating

6: 92 percent / MCPBA

7: TMSN₃, ZnCl₂

8: H₂ / Pd/C

9: NaHCO₃

10: 92 percent / imidazole

11: NaOH

12: 1.) 1-oxa-2-oxo-3-thia-indolizinium chloride, DMAP, CBrCl₃, 2.) DBU

With 1H-imidazole; dmap; sodium hydroxide; Bromotrichloromethane; trimethylsilylazide; 1-oxa-2-oxo-3-thiaindolizinium chloride; hydrogen; iodine; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 3-chloro-benzenecarboperoxoic acid; potassium iodide; zinc(II) chloride; silver(l) oxide; palladium on activated charcoal; In 1,2-dichloro-ethane;
DOI:10.1246/cl.1987.29