(+)-tert-butyl {(1S)-1-[(benzyloxy)methyl]prop-2-en-1-yl}methoxycarbamate

Base Information

• Chemical Name: (+)-tert-butyl {(1S)-1-[(benzyloxy)methyl]prop-2-en-1-yl}methoxycarbamate
• CAS No.: 1304540-10-0
• Molecular Formula: C₁₇H₂₅NO₄
• Molecular Weight: 307.39

Synonyms:(+)-tert-butyl {(1S)-1-[(benzyloxy)methyl]prop-2-en-1-yl}methoxycarbamate

Chemical Property of (+)-tert-butyl {(1S)-1-[(benzyloxy)methyl]prop-2-en-1-yl}methoxycarbamate

Chemical Property:

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Technology Process of (+)-tert-butyl {(1S)-1-[(benzyloxy)methyl]prop-2-en-1-yl}methoxycarbamate

There total 4 articles about (+)-tert-butyl {(1S)-1-[(benzyloxy)methyl]prop-2-en-1-yl}methoxycarbamate 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%

(2E)-4-[(phenylmethyl)oxy]-2-buten-1-yl methyl carbonate + N-(tert-butoxycarbonyl)-O-methylhydroxylamine (58377-44-9) → tert-butyl [(2E)-4-(benzyloxy)but-2-en-1-yl]methoxycarbamate (1304540-20-2) + (+)-tert-butyl {(1S)-1-[(benzyloxy)methyl]prop-2-en-1-yl}methoxycarbamate (1304540-10-0)

Guidance literature:

With dichlorobis(η4-dibenzo[a,e]cyclooctatetraene)diiridium(I); [O,O’-((S)-1,1′-dinaphthyl-2,2′-diyl)-N,N′-di-(S,S)-1-(2-methoxyphenyl)ethylphosphoramidite]; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; at 50 ℃; for 20h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1021/ol200688d

Reference yield:

(2E)-4-[(phenylmethyl)oxy]-2-buten-1-yl methyl carbonate + N-(tert-butoxycarbonyl)-O-methylhydroxylamine (58377-44-9) → tert-butyl [(2E)-4-(benzyloxy)but-2-en-1-yl]methoxycarbamate (1304540-20-2) + (-)-tert-butyl {(1R)-1-[(benzyloxy)methyl]prop-2-en-1-yl}methoxycarbamate + (+)-tert-butyl {(1S)-1-[(benzyloxy)methyl]prop-2-en-1-yl}methoxycarbamate (1304540-10-0)

Guidance literature:

With dichlorobis(η4-dibenzo[a,e]cyclooctatetraene)diiridium(I); 1,8-diazabicyclo[5.4.0]undec-7-ene; (3,5-dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-(1-phenyl-ethyl)-amine; In tetrahydrofuran; at 50 ℃; for 1h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1021/ol200688d

Reference yield:

C13H16O4 + N-(tert-butoxycarbonyl)-O-methylhydroxylamine (58377-44-9) → (+)-tert-butyl {(1S)-1-[(benzyloxy)methyl]prop-2-en-1-yl}methoxycarbamate (1304540-10-0) + C17H25NO4

Guidance literature:

With C₅₆H₄₈IrNO₂P⁽¹⁺⁾*CF₃O₃S^(1-); 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; at 50 ℃; for 3h; Overall yield = 77 %; enantioselective reaction;

DOI:10.1002/chem.201302735

upstream raw materials:

N-(tert-butoxycarbonyl)-O-methylhydroxylamine

Downstream raw materials:

(+)-N-{(1'S)-1-[(benzyloxy)methyl]prop-2-en-1-yl}-N-methoxybut-3-enamide

(-)-(6S)-6-[(benzyloxy)methyl]-1-methoxy-3,6-dihydropyridin-2(1H)-one

(+)-(5S,6R)-6-[(benzyloxy)methyl]-5-hydroxy-1-methoxy-5,6-dihydropyridin-2(1H)-one

N-{(1S)-1-[(benzyloxy)methyl]prop-2-en-1-yl}-O-methylhydroxylamine

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