1-[(2S,3R)-2-amino-4-benzyloxy-N-(tert-butoxycarbonyl)-3-hydroxybutyryloxy]-3-(tri-O-benzyl-α-L-fucopyranosyl)propane

Base Information

Chemical Name:1-[(2S,3R)-2-amino-4-benzyloxy-N-(tert-butoxycarbonyl)-3-hydroxybutyryloxy]-3-(tri-O-benzyl-α-L-fucopyranosyl)propane
CAS No.:181629-32-3
Molecular Formula:C₄₆H₅₇NO₁₀
Molecular Weight:783.959
Hs Code.:

Synonyms:1-[(2S,3R)-2-amino-4-benzyloxy-N-(tert-butoxycarbonyl)-3-hydroxybutyryloxy]-3-(tri-O-benzyl-α-L-fucopyranosyl)propane

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Chemical Property of 1-[(2S,3R)-2-amino-4-benzyloxy-N-(tert-butoxycarbonyl)-3-hydroxybutyryloxy]-3-(tri-O-benzyl-α-L-fucopyranosyl)propane

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Technology Process of 1-[(2S,3R)-2-amino-4-benzyloxy-N-(tert-butoxycarbonyl)-3-hydroxybutyryloxy]-3-(tri-O-benzyl-α-L-fucopyranosyl)propane

There total 7 articles about 1-[(2S,3R)-2-amino-4-benzyloxy-N-(tert-butoxycarbonyl)-3-hydroxybutyryloxy]-3-(tri-O-benzyl-α-L-fucopyranosyl)propane 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: 68.0%

: 181629-30-1
3-(tri-O-benzyl-α-L-fucopyranosyl)-1-propyl bromide

: Caesium; (2S,3R)-4-benzyloxy-2-tert-butoxycarbonylamino-3-hydroxy-butyrate

: 181629-32-3
1-[(2S,3R)-2-amino-4-benzyloxy-N-(tert-butoxycarbonyl)-3-hydroxybutyryloxy]-3-(tri-O-benzyl-α-L-fucopyranosyl)propane

Guidance literature:: In N,N-dimethyl-formamide; at 40 ℃; for 12h;
DOI:10.1016/0968-0896(96)00127-7

Reference yield:

: 100-39-0
benzyl bromide

: 181629-32-3
1-[(2S,3R)-2-amino-4-benzyloxy-N-(tert-butoxycarbonyl)-3-hydroxybutyryloxy]-3-(tri-O-benzyl-α-L-fucopyranosyl)propane

Guidance literature:: Multi-step reaction with 4 steps

1: 99 percent / Bu₄NI, NaH / tetrahydrofuran / 17 h / 23 °C

2: 1.) 9-borabicyclo<3.3.1>nonane, 2.) 1 N NaOH, 30percent H₂O₂ / 1.) THF, reflux, 3 h, 2.) THF, EtOH, 23 deg C, 14 h

3: 83 percent / CBr₄, PPh₃ / CH₂Cl₂ / 4 h / 23 °C

4: 68 percent / dimethylformamide / 12 h / 40 °C

With sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; carbon tetrabromide; dihydrogen peroxide; tetra-(n-butyl)ammonium iodide; sodium hydride; triphenylphosphine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/0968-0896(96)00127-7

Reference yield:

: 145987-57-1
3,4,5-tri-O-acetyl-2,6-anhydro-1,7,8,9-tetradeoxy-L-glycero-D-galacto-non-8-enitol

: 181629-32-3
1-[(2S,3R)-2-amino-4-benzyloxy-N-(tert-butoxycarbonyl)-3-hydroxybutyryloxy]-3-(tri-O-benzyl-α-L-fucopyranosyl)propane

Guidance literature:: Multi-step reaction with 5 steps

1: 74 percent / NaOMe / methanol / 15 h / 23 °C

2: 99 percent / Bu₄NI, NaH / tetrahydrofuran / 17 h / 23 °C

3: 1.) 9-borabicyclo<3.3.1>nonane, 2.) 1 N NaOH, 30percent H₂O₂ / 1.) THF, reflux, 3 h, 2.) THF, EtOH, 23 deg C, 14 h

4: 83 percent / CBr₄, PPh₃ / CH₂Cl₂ / 4 h / 23 °C

5: 68 percent / dimethylformamide / 12 h / 40 °C

With sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; carbon tetrabromide; dihydrogen peroxide; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/0968-0896(96)00127-7