(6E)-5-[allyl(tert-butoxycarbonyl)amino]-5,6,7-trideoxy-7-phenyl-D-gluco-hept-6-enitol

Base Information

• Chemical Name: (6E)-5-[allyl(tert-butoxycarbonyl)amino]-5,6,7-trideoxy-7-phenyl-D-gluco-hept-6-enitol
• CAS No.: 691905-78-9
• Molecular Formula: C₂₁H₃₁NO₆
• Molecular Weight: 393.48

Synonyms:(6E)-5-[allyl(tert-butoxycarbonyl)amino]-5,6,7-trideoxy-7-phenyl-D-gluco-hept-6-enitol

Chemical Property of (6E)-5-[allyl(tert-butoxycarbonyl)amino]-5,6,7-trideoxy-7-phenyl-D-gluco-hept-6-enitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of (6E)-5-[allyl(tert-butoxycarbonyl)amino]-5,6,7-trideoxy-7-phenyl-D-gluco-hept-6-enitol

There total 3 articles about (6E)-5-[allyl(tert-butoxycarbonyl)amino]-5,6,7-trideoxy-7-phenyl-D-gluco-hept-6-enitol 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: 80.0%

di-tert-butyl dicarbonate (24424-99-5) + (6E)-5-(allylamino)-5,6,7-trideoxy-7-phenyl-D-gluco-hept-6-enitol (691905-77-8) → (6E)-5-[allyl(tert-butoxycarbonyl)amino]-5,6,7-trideoxy-7-phenyl-D-gluco-hept-6-enitol (691905-78-9)

Guidance literature:

With triethylamine; In methanol; at 20 ℃; for 72h; Inert atmosphere;

DOI:10.1021/jo902355p

Reference yield:

L-xylose (609-06-3) → (6E)-5-[allyl(tert-butoxycarbonyl)amino]-5,6,7-trideoxy-7-phenyl-D-gluco-hept-6-enitol (691905-78-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 73 percent / ethanol / 16 h / 20 °C

2: 51 percent / triethylamine / acetonitrile; dimethylformamide / 19 h / 0 - 20 °C

With triethylamine; In ethanol; N,N-dimethyl-formamide; acetonitrile; 1: Petasis reaction;

DOI:10.1021/jo049806y

Reference yield:

trans-2-phenylvinylboronic acid (6783-05-7) → (6E)-5-[allyl(tert-butoxycarbonyl)amino]-5,6,7-trideoxy-7-phenyl-D-gluco-hept-6-enitol (691905-78-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 73 percent / ethanol / 16 h / 20 °C

2: 51 percent / triethylamine / acetonitrile; dimethylformamide / 19 h / 0 - 20 °C

With triethylamine; In ethanol; N,N-dimethyl-formamide; acetonitrile; 1: Petasis reaction;

DOI:10.1021/jo049806y

upstream raw materials:

di-tert-butyl dicarbonate

(6E)-5-(allylamino)-5,6,7-trideoxy-7-phenyl-D-gluco-hept-6-enitol

L-xylose

trans-2-phenylvinylboronic acid

Downstream raw materials:

(6E)-5-[allyl(tert-butylcarbonyl)amino]-1-O-triphenylmethyl-5,6,7-trideoxy-7-phenyl-D-gluco-hept-6-enitol

tert-butyl (2R)-2-[(2S,3S)-4-(triphenylmethyloxy)-1,2,3-trihydroxybutyl]-2,5-dihydro-1H-pyrrole-1-carboxylate

tert-butyl (2R,3S,4R)-3,4-dihydroxy-2-[(2S,3S)-1,2,3-trihydroxy-4-(triphenylmethyloxy)butyl]pyrrolidine-1-carboxylate

tert-butyl (2R,3S,4R)-3,4-bis(benzyloxy)-2-[(1R,2S,3S)-1,2,3-tris(benzyloxy)-4-(triphenylmethyloxy)butyl]pyrrolidine-1-carboxylate

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