[N-(benzyloxycarbonyl)aminopropyl (2-acetamido-3,4-di-O-benzyl-2-deoxy-β-D-mannopyranosidyl)]methyl C-(2-acetamido-6-O-acetyl-3,4-di-O-benzyl-2-deoxy-α-D-mannopyranosyl)methanephosphonate

Base Information

Chemical Name:[N-(benzyloxycarbonyl)aminopropyl (2-acetamido-3,4-di-O-benzyl-2-deoxy-β-D-mannopyranosidyl)]methyl C-(2-acetamido-6-O-acetyl-3,4-di-O-benzyl-2-deoxy-α-D-mannopyranosyl)methanephosphonate
CAS No.:952139-86-5
Molecular Formula:C₅₉H₇₂N₃O₁₆P
Molecular Weight:1110.2
Hs Code.:

[N-(benzyloxycarbonyl)aminopropyl (2-acetamido-3,4-di-O-benzyl-2-deoxy-β-D-mannopyranosidyl)]methyl C-(2-acetamido-6-O-acetyl-3,4-di-O-benzyl-2-deoxy-α-D-mannopyranosyl)methanephosphonate

Synonyms:[N-(benzyloxycarbonyl)aminopropyl (2-acetamido-3,4-di-O-benzyl-2-deoxy-β-D-mannopyranosidyl)]methyl C-(2-acetamido-6-O-acetyl-3,4-di-O-benzyl-2-deoxy-α-D-mannopyranosyl)methanephosphonate

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Chemical Property of [N-(benzyloxycarbonyl)aminopropyl (2-acetamido-3,4-di-O-benzyl-2-deoxy-β-D-mannopyranosidyl)]methyl C-(2-acetamido-6-O-acetyl-3,4-di-O-benzyl-2-deoxy-α-D-mannopyranosyl)methanephosphonate

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Technology Process of [N-(benzyloxycarbonyl)aminopropyl (2-acetamido-3,4-di-O-benzyl-2-deoxy-β-D-mannopyranosidyl)]methyl C-(2-acetamido-6-O-acetyl-3,4-di-O-benzyl-2-deoxy-α-D-mannopyranosyl)methanephosphonate

There total 21 articles about [N-(benzyloxycarbonyl)aminopropyl (2-acetamido-3,4-di-O-benzyl-2-deoxy-β-D-mannopyranosidyl)]methyl C-(2-acetamido-6-O-acetyl-3,4-di-O-benzyl-2-deoxy-α-D-mannopyranosyl)methanephosphonate 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: 90.0%

: 858109-02-1
N-(benzyloxycarbonyl)aminopropyl 2-acetamido-3,4-di-O-benzyl-2-deoxy-β-D-mannopyranoside

: methyl C-(2-acetamido-6-O-acetyl-3,4-di-O-benzyl-2-deoxy-α-D-mannopyranosyl)methanephosphonate triethylammonium salt

: 952139-86-5
[N-(benzyloxycarbonyl)aminopropyl (2-acetamido-3,4-di-O-benzyl-2-deoxy-β-D-mannopyranosidyl)]methyl C-(2-acetamido-6-O-acetyl-3,4-di-O-benzyl-2-deoxy-α-D-mannopyranosyl)methanephosphonate

Guidance literature:: With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20 ℃; for 24h;
DOI:10.1002/chem.200601743

Reference yield:

: 858109-04-3
[N-(benzyloxycarbonyl)aminopropyl (2-acetamido-3,4-di-O-benzyl-2-deoxy-β-D-mannopyranosidyl)]methyl C-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-α-D-mannopyranosyl)methanephosphonate

: 108-24-7
acetic anhydride

: 952139-86-5
[N-(benzyloxycarbonyl)aminopropyl (2-acetamido-3,4-di-O-benzyl-2-deoxy-β-D-mannopyranosidyl)]methyl C-(2-acetamido-6-O-acetyl-3,4-di-O-benzyl-2-deoxy-α-D-mannopyranosyl)methanephosphonate

Guidance literature:: With acetic acid; zinc(II) chloride;
DOI:10.1055/s-2005-865226

Reference yield:

: (2S,3S,4R,5S,6R)-3-Azido-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-carbaldehyde

: 952139-86-5
[N-(benzyloxycarbonyl)aminopropyl (2-acetamido-3,4-di-O-benzyl-2-deoxy-β-D-mannopyranosidyl)]methyl C-(2-acetamido-6-O-acetyl-3,4-di-O-benzyl-2-deoxy-α-D-mannopyranosyl)methanephosphonate

Guidance literature:: Multi-step reaction with 9 steps

1: aq. NaBH₄ / tetrahydrofuran / 20 °C

2: PPh₃ / tetrahydrofuran / 20 °C

3: methanol / 20 °C

4: 88 percent / pyridine / CH₂Cl₂ / 20 °C

5: NaI / butan-2-one / 100 °C

6: 100 °C

7: 62 percent / PhSH / tetrahydrofuran / 20 °C

8: 97 percent / PPh₃; DIAD / tetrahydrofuran / 20 °C

9: ZnCl₂; CH₃COOH

With pyridine; sodium tetrahydroborate; di-isopropyl azodicarboxylate; acetic acid; thiophenol; triphenylphosphine; sodium iodide; zinc(II) chloride; In tetrahydrofuran; methanol; dichloromethane; butanone; 8: Mitsunobu reaction;
DOI:10.1055/s-2005-865226