5-azido-2,3,5-trideoxy-6-O-(3-(((1R,S)-1-tert-butoxycarbonylamino)ethyl)benzyl)-2-isopropyl-D-glucono-1,4-lactone

Base Information

• Chemical Name: 5-azido-2,3,5-trideoxy-6-O-(3-(((1R,S)-1-tert-butoxycarbonylamino)ethyl)benzyl)-2-isopropyl-D-glucono-1,4-lactone
• CAS No.: 1056675-51-4
• Molecular Formula: C₂₃H₃₄N₄O₅
• Molecular Weight: 446.547

Synonyms:5-azido-2,3,5-trideoxy-6-O-(3-(((1R,S)-1-tert-butoxycarbonylamino)ethyl)benzyl)-2-isopropyl-D-glucono-1,4-lactone

Chemical Property of 5-azido-2,3,5-trideoxy-6-O-(3-(((1R,S)-1-tert-butoxycarbonylamino)ethyl)benzyl)-2-isopropyl-D-glucono-1,4-lactone

Chemical Property:

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Technology Process of 5-azido-2,3,5-trideoxy-6-O-(3-(((1R,S)-1-tert-butoxycarbonylamino)ethyl)benzyl)-2-isopropyl-D-glucono-1,4-lactone

There total 2 articles about 5-azido-2,3,5-trideoxy-6-O-(3-(((1R,S)-1-tert-butoxycarbonylamino)ethyl)benzyl)-2-isopropyl-D-glucono-1,4-lactone 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: 60.0%

2,3-dideoxy-6-O-(3-(((1R,S)-1-tert-butoxycarbonylamino)ethyl)benzyl)-2-isopropyl-D-glucono-1,4-lactone (1056675-47-8) → 5-azido-2,3,5-trideoxy-6-O-(3-(((1R,S)-1-tert-butoxycarbonylamino)ethyl)benzyl)-2-isopropyl-D-glucono-1,4-lactone (1056675-51-4)

Guidance literature:

2,3-dideoxy-6-O-(3-(((1R,S)-1-tert-butoxycarbonylamino)ethyl)benzyl)-2-isopropyl-D-glucono-1,4-lactone; With pyridine; trifluoromethylsulfonic anhydride; In dichloromethane; at 0 ℃; for 1h;

With sodium azide; In N,N-dimethyl-formamide; at 70 ℃; for 1h;

Reference yield:

C24H34F3NO8S → 5-azido-2,3,5-trideoxy-6-O-(3-(((1R,S)-1-tert-butoxycarbonylamino)ethyl)benzyl)-2-isopropyl-D-glucono-1,4-lactone (1056675-51-4)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 70 ℃;

DOI:10.1016/j.bmcl.2010.10.140

Reference yield:

5-azido-2,3,5-trideoxy-6-O-(3-(((1R,S)-1-tert-butoxycarbonylamino)ethyl)benzyl)-2-isopropyl-D-glucono-1,4-lactone (1056675-51-4) + L-valine benzylamide (106566-02-3,120369-25-7,144902-31-8) → (2S,4S,5S)-5-azido-6-(3-((1RS)-1-(t-butoxycarbonylamino)ethyl)benzyloxy)-4-hydroxy-2-isopropyl-hexanoic acid ((S)-1-benzylcarbamoyl-2-methyl-propyl)-amide (1056675-55-8)

Guidance literature:

With 2-hydroxypyridin; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 70 ℃;

DOI:10.1016/j.bmcl.2010.10.140

upstream raw materials:

2,3-dideoxy-6-O-(3-(((1R,S)-1-tert-butoxycarbonylamino)ethyl)benzyl)-2-isopropyl-D-glucono-1,4-lactone

Downstream raw materials:

(2S,4S,5S)-5-azido-6-(3-((1RS)-1-(t-butoxycarbonylamino)ethyl)benzyloxy)-4-hydroxy-2-isopropyl-hexanoic acid ((S)-1-benzylcarbamoyl-2-methyl-propyl)-amide

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