N-[(2S,5S,6R)-6-((3aR,4S,6S,7R,7aR)-6-Azido-4-methoxy-3-methyl-2-oxo-octahydro-benzooxazol-7-yloxy)-5-iodo-tetrahydro-pyran-2-ylmethyl]-2,2,2-trifluoro-N-((R)-1-phenyl-ethyl)-acetamide

Base Information

• Chemical Name: N-[(2S,5S,6R)-6-((3aR,4S,6S,7R,7aR)-6-Azido-4-methoxy-3-methyl-2-oxo-octahydro-benzooxazol-7-yloxy)-5-iodo-tetrahydro-pyran-2-ylmethyl]-2,2,2-trifluoro-N-((R)-1-phenyl-ethyl)-acetamide
• CAS No.: 213132-41-3
• Molecular Formula: C₂₅H₃₁F₃IN₅O₆
• Molecular Weight: 681.451

Synonyms:N-[(2S,5S,6R)-6-((3aR,4S,6S,7R,7aR)-6-Azido-4-methoxy-3-methyl-2-oxo-octahydro-benzooxazol-7-yloxy)-5-iodo-tetrahydro-pyran-2-ylmethyl]-2,2,2-trifluoro-N-((R)-1-phenyl-ethyl)-acetamide

Chemical Property of N-[(2S,5S,6R)-6-((3aR,4S,6S,7R,7aR)-6-Azido-4-methoxy-3-methyl-2-oxo-octahydro-benzooxazol-7-yloxy)-5-iodo-tetrahydro-pyran-2-ylmethyl]-2,2,2-trifluoro-N-((R)-1-phenyl-ethyl)-acetamide

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Technology Process of N-[(2S,5S,6R)-6-((3aR,4S,6S,7R,7aR)-6-Azido-4-methoxy-3-methyl-2-oxo-octahydro-benzooxazol-7-yloxy)-5-iodo-tetrahydro-pyran-2-ylmethyl]-2,2,2-trifluoro-N-((R)-1-phenyl-ethyl)-acetamide

There total 3 articles about N-[(2S,5S,6R)-6-((3aR,4S,6S,7R,7aR)-6-Azido-4-methoxy-3-methyl-2-oxo-octahydro-benzooxazol-7-yloxy)-5-iodo-tetrahydro-pyran-2-ylmethyl]-2,2,2-trifluoro-N-((R)-1-phenyl-ethyl)-acetamide 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: 62.0%

(2S)-2-[N-trifluoroacetyl-N-((R)-phenylethyl)aminomethyl]-3,4-dihydro-2H-pyran (91704-05-1) + (3aR,4S,6S,7R,7aR)-6-Azido-7-hydroxy-4-methoxy-3-methyl-hexahydro-benzooxazol-2-one → N-[(2S,5S,6R)-6-((3aR,4S,6S,7R,7aR)-6-Azido-4-methoxy-3-methyl-2-oxo-octahydro-benzooxazol-7-yloxy)-5-iodo-tetrahydro-pyran-2-ylmethyl]-2,2,2-trifluoro-N-((R)-1-phenyl-ethyl)-acetamide (213132-41-3) + N-[(2S,5R,6S)-6-((3aR,4S,6S,7R,7aR)-6-Azido-4-methoxy-3-methyl-2-oxo-octahydro-benzooxazol-7-yloxy)-5-iodo-tetrahydro-pyran-2-ylmethyl]-2,2,2-trifluoro-N-((R)-1-phenyl-ethyl)-acetamide

Guidance literature:

With iodonium di(2,4,6-trimethylpyridine) perchlorate; In dichloromethane; acetonitrile; at 20 ℃; for 16h;

DOI:10.1002/(SICI)1099-0690(199809)1998:9<1935::AID-EJOC1935>3.0.CO;2-Y

Reference yield: 60.0%

(2S)-2-[N-trifluoroacetyl-N-((R)-phenylethyl)aminomethyl]-3,4-dihydro-2H-pyran (91704-05-1) + (3aR,4S,6S,7R,7aR)-6-Azido-7-hydroxy-4-methoxy-3-methyl-hexahydro-benzooxazol-2-one → 2,2,2-Trifluoro-N-((S)-5-iodo-3,4-dihydro-2H-pyran-2-ylmethyl)-N-((R)-1-phenyl-ethyl)-acetamide + N-[(2S,5S,6R)-6-((3aR,4S,6S,7R,7aR)-6-Azido-4-methoxy-3-methyl-2-oxo-octahydro-benzooxazol-7-yloxy)-5-iodo-tetrahydro-pyran-2-ylmethyl]-2,2,2-trifluoro-N-((R)-1-phenyl-ethyl)-acetamide (213132-41-3) + N-[(2S,5R,6S)-6-((3aR,4S,6S,7R,7aR)-6-Azido-4-methoxy-3-methyl-2-oxo-octahydro-benzooxazol-7-yloxy)-5-iodo-tetrahydro-pyran-2-ylmethyl]-2,2,2-trifluoro-N-((R)-1-phenyl-ethyl)-acetamide

Guidance literature:

With iodonium di(2,4,6-trimethylpyridine) perchlorate; In acetonitrile; at 20 ℃; for 24h;

DOI:10.1002/(SICI)1099-0690(199809)1998:9<1935::AID-EJOC1935>3.0.CO;2-Y

Reference yield: 42.0%

N-iodo-succinimide (516-12-1) + (2S)-2-[N-trifluoroacetyl-N-((R)-phenylethyl)aminomethyl]-3,4-dihydro-2H-pyran (91704-05-1) → N-[(2S,5S,6R)-6-((3aR,4S,6S,7R,7aR)-6-Azido-4-methoxy-3-methyl-2-oxo-octahydro-benzooxazol-7-yloxy)-5-iodo-tetrahydro-pyran-2-ylmethyl]-2,2,2-trifluoro-N-((R)-1-phenyl-ethyl)-acetamide (213132-41-3) + 1-N-succinimido-1,2,3,4,6-pentadeoxy-2β-iodo-6-[trifluoroacetyl-((1R)-phenylethyl)]amino-α-D-hexopyranoside

Guidance literature:

In acetonitrile;

DOI:10.1002/(SICI)1099-0690(199809)1998:9<1935::AID-EJOC1935>3.0.CO;2-Y

upstream raw materials:

N-iodo-succinimide

(2S)-2-[N-trifluoroacetyl-N-((R)-phenylethyl)aminomethyl]-3,4-dihydro-2H-pyran

Downstream raw materials:

N-[(2S,5S,6R)-6-((3aR,4S,6S,7R,7aR)-6-Azido-4-methoxy-3-methyl-2-oxo-octahydro-benzooxazol-7-yloxy)-5-(2,2,6,6-tetramethyl-piperidin-1-yloxy)-tetrahydro-pyran-2-ylmethyl]-2,2,2-trifluoro-N-((R)-1-phenyl-ethyl)-acetamide

({[(1S,2R,3R,4S,6S)-4-Azido-2-hydroxy-6-methoxy-3-((2R,6S)-6-{[methyl-((R)-1-phenyl-ethyl)-amino]-methyl}-5,6-dihydro-2H-pyran-2-yloxy)-cyclohexyl]-methyl-carbamoyl}-methyl)-carbamic acid benzyl ester

(3aR,4S,6S,7R,7aR)-6-Azido-7-((2R,3S,6S)-3-iodo-6-{[methyl-((R)-1-phenyl-ethyl)-amino]-methyl}-tetrahydro-pyran-2-yloxy)-4-methoxy-3-methyl-hexahydro-benzooxazol-2-one

(1R,2R,3S,5S,6S)-3-Azido-5-methoxy-6-methylamino-2-((2R,6S)-6-{[methyl-((R)-1-phenyl-ethyl)-amino]-methyl}-5,6-dihydro-2H-pyran-2-yloxy)-cyclohexanol

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