benzyl (1S,4R,6R)-4-[3-(tert-butyldimethylsilyloxy)propyl]-7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylate

Base Information

• Chemical Name: benzyl (1S,4R,6R)-4-[3-(tert-butyldimethylsilyloxy)propyl]-7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylate
• CAS No.: 1207461-47-9
• Molecular Formula: C₂₂H₃₅NO₄Si
• Molecular Weight: 405.61

Synonyms:benzyl (1S,4R,6R)-4-[3-(tert-butyldimethylsilyloxy)propyl]-7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylate

Chemical Property of benzyl (1S,4R,6R)-4-[3-(tert-butyldimethylsilyloxy)propyl]-7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylate

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Technology Process of benzyl (1S,4R,6R)-4-[3-(tert-butyldimethylsilyloxy)propyl]-7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylate

There total 1 articles about benzyl (1S,4R,6R)-4-[3-(tert-butyldimethylsilyloxy)propyl]-7-oxa-3-azabicyclo[4.1.0]heptane-3-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: 83.0%

benzyl (R)-6-[3-(tert-butyldimethylsilyloxy)propyl]-5,6-dihydro-1(2H)-pyridinecarboxylate (1207461-43-5) → benzyl (1S,4R,6R)-4-[3-(tert-butyldimethylsilyloxy)propyl]-7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylate (1207461-47-9)

Guidance literature:

With Oxone; 1,1,1-trifluoro-2-propanone; disodium ethylenediaminetetraacetic acid; sodium hydrogencarbonate; In water; acetonitrile; at 0 - 20 ℃; optical yield given as %de; stereoselective reaction; Inert atmosphere;

DOI:10.1021/ol902920u

Reference yield: 78.0%

benzyl (1S,4R,6R)-4-[3-(tert-butyldimethylsilyloxy)propyl]-7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylate (1207461-47-9) → benzyl (2R,4R,5R)-4-azido-2-(3-(tert-butyldimethylsilyloxy)propyl)-5-hydroxypiperidine-1-carboxylate

Guidance literature:

With sodium azide; ammonium chloride; In methanol; water; at 65 ℃; stereoselective reaction; Inert atmosphere;

DOI:10.1021/ol902920u

Reference yield: 78.0%

benzyl (1S,4R,6R)-4-[3-(tert-butyldimethylsilyloxy)propyl]-7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylate (1207461-47-9) → C22H36N4O4Si (1207461-48-0)

Guidance literature:

With sodium azide; water; ammonium chloride; In methanol; at 65 ℃;

DOI:10.1021/ol201592g

upstream raw materials:

benzyl (R)-6-[3-(tert-butyldimethylsilyloxy)propyl]-5,6-dihydro-1(2H)-pyridinecarboxylate

Downstream raw materials:

C₂₂H₃₆N₄O₄Si

(2R,4S,5S)-benzyl 4-amino-2-(3-((tert-butyldimethylsilyl)oxy)propyl)-5-hydroxypiperidine-1-carboxylate

(2R,4S,5S)-benzyl 2-(3-((tert-butyldimethylsilyl)oxy)propyl)-5-hydroxy-4-(4-methylphenylsulfonamido)piperidine-1-carboxylate

(2R,4S,5S)-benzyl 5-hydroxy-2-(3-hydroxypropyl)-4-(4-methylphenylsulfonamido)piperidine-1-carboxylate

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