N-Boc-6-amino-2,5-anhydro-3,4-di-O-benzyl-6-deoxy-D-glucitol

Base Information

• Chemical Name: N-Boc-6-amino-2,5-anhydro-3,4-di-O-benzyl-6-deoxy-D-glucitol
• CAS No.: 746656-97-3
• Molecular Formula: C₂₅H₃₃NO₆
• Molecular Weight: 443.54
• Mol file: 746656-97-3.mol

Synonyms:N-Boc-6-amino-2,5-anhydro-3,4-di-O-benzyl-6-deoxy-D-glucitol

Chemical Property of N-Boc-6-amino-2,5-anhydro-3,4-di-O-benzyl-6-deoxy-D-glucitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-Boc-6-amino-2,5-anhydro-3,4-di-O-benzyl-6-deoxy-D-glucitol

There total 2 articles about N-Boc-6-amino-2,5-anhydro-3,4-di-O-benzyl-6-deoxy-D-glucitol 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:

6-azido-3,4-di-O-benzyl-6-deoxy-D-mannitol (155696-77-8) → N-Boc-6-amino-2,5-anhydro-3,4-di-O-benzyl-6-deoxy-D-glucitol (746656-97-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: TsCl; pyridine; DMAP / 3 h / 0 - 20 °C

1.2: K₂CO₃ / methanol / 10 h / 20 °C

2.1: Ph₃P / methanol / 2 h

2.2: methanol

With pyridine; dmap; p-toluenesulfonyl chloride; triphenylphosphine; In methanol;

DOI:10.1016/j.tetlet.2007.07.158

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) + 2,5-anhydro-6-azido-3,4-di-O-benzyl-6-deoxy-D-glucitol (171973-88-9) → N-Boc-6-amino-2,5-anhydro-3,4-di-O-benzyl-6-deoxy-D-glucitol (746656-97-3)

Guidance literature:

2,5-anhydro-6-azido-3,4-di-O-benzyl-6-deoxy-D-glucitol; With triphenylphosphine; In methanol; for 2h;

di-tert-butyl dicarbonate; In methanol; Further stages.;

DOI:10.1016/j.tetlet.2007.07.158

Reference yield: 91.0%

tert-butylchlorodiphenylsilane (58479-61-1) + N-Boc-6-amino-2,5-anhydro-3,4-di-O-benzyl-6-deoxy-D-glucitol (746656-97-3) → [5-(tert-butyl-diphenyl-silanyloxymethyl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl]-carbamic acid tert-butyl ester (779358-55-3)

Guidance literature:

N-Boc-6-amino-2,5-anhydro-3,4-di-O-benzyl-6-deoxy-D-glucitol; With hydrogen; palladium dihydroxide; In methanol; for 8h;

tert-butylchlorodiphenylsilane; With dmap; triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 3h;

DOI:10.1016/j.tet.2004.07.032

upstream raw materials:

di-tert-butyl dicarbonate

2,5-anhydro-6-azido-3,4-di-O-benzyl-6-deoxy-D-glucitol

6-azido-3,4-di-O-benzyl-6-deoxy-D-mannitol

Downstream raw materials:

3,4-bis-benzyloxy-5-(tert-butoxycarbonylamino-methyl)-tetrahydro-furan-2-carboxylic acid tert-butyl ester

[5-(tert-butyl-diphenyl-silanyloxymethyl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl]-carbamic acid tert-butyl ester