2-azido-6-(benzyloxy)-5-(4-methoxybenzyloxy)hexane-1,3-diol

Base Information

• Chemical Name: 2-azido-6-(benzyloxy)-5-(4-methoxybenzyloxy)hexane-1,3-diol
• CAS No.: 1321980-67-9
• Molecular Formula: C₂₁H₂₇N₃O₅
• Molecular Weight: 401.462
• Mol file: 1321980-67-9.mol

Synonyms:2-azido-6-(benzyloxy)-5-(4-methoxybenzyloxy)hexane-1,3-diol

Chemical Property of 2-azido-6-(benzyloxy)-5-(4-methoxybenzyloxy)hexane-1,3-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-azido-6-(benzyloxy)-5-(4-methoxybenzyloxy)hexane-1,3-diol

There total 9 articles about 2-azido-6-(benzyloxy)-5-(4-methoxybenzyloxy)hexane-1,3-diol 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: 85.0%

(3-{3-(benzyloxy)-2-[(4-methoxybenzyl)oxy]propyl}oxiran-2-yl)methanol (1321980-64-6) → C21H27N3O5 + 2-azido-6-(benzyloxy)-5-(4-methoxybenzyloxy)hexane-1,3-diol (1321980-67-9)

Guidance literature:

With sodium azide; Trimethyl borate; In N,N-dimethyl-formamide; at 90 ℃; for 3.5h; regioselective reaction;

DOI:10.1055/s-0030-1260546

Reference yield:

C19H24O4 (1321980-61-3) → C21H27N3O5 + 2-azido-6-(benzyloxy)-5-(4-methoxybenzyloxy)hexane-1,3-diol (1321980-67-9)

Guidance literature:

Multi-step reaction with 5 steps

1: dimethyl sulfoxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dichloromethane / 3 h / 0 - 20 °C

2: dichloromethane / 2 h / 20 °C

3: diisobutylaluminium hydride / dichloromethane / 0.5 h / -78 - -10 °C

4: titanium(IV) isopropylate; tert.-butylhydroperoxide; L-(+)-diisopropyl tartrate / dichloromethane / 20 h / -20 °C

5: sodium azide; Trimethyl borate / N,N-dimethyl-formamide / 3.5 h / 90 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium azide; Trimethyl borate; L-(+)-diisopropyl tartrate; diisobutylaluminium hydride; dimethyl sulfoxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In dichloromethane; N,N-dimethyl-formamide; 1: Swern oxidation / 4: Sharpless epoxidation;

DOI:10.1055/s-0030-1260546

Reference yield:

C23H28O5 (1321980-62-4) → C21H27N3O5 + 2-azido-6-(benzyloxy)-5-(4-methoxybenzyloxy)hexane-1,3-diol (1321980-67-9)

Guidance literature:

Multi-step reaction with 3 steps

1: diisobutylaluminium hydride / dichloromethane / 0.5 h / -78 - -10 °C

2: titanium(IV) isopropylate; tert.-butylhydroperoxide; L-(+)-diisopropyl tartrate / dichloromethane / 20 h / -20 °C

3: sodium azide; Trimethyl borate / N,N-dimethyl-formamide / 3.5 h / 90 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium azide; Trimethyl borate; L-(+)-diisopropyl tartrate; diisobutylaluminium hydride; In dichloromethane; N,N-dimethyl-formamide; 2: Sharpless epoxidation;

DOI:10.1055/s-0030-1260546

upstream raw materials:

C₁₉H₂₄O₄

C₂₃H₂₈O₅

C₂₁H₂₆O₄

(3-{3-(benzyloxy)-2-[(4-methoxybenzyl)oxy]propyl}oxiran-2-yl)methanol

Downstream raw materials:

C₁₆H₂₃N₃O₄

C₁₇H₂₅N₃O₆S

(4aR,6S,7aS)-6-(benzyloxymethyl)-2,2-dimethylhexahydro[1,3]dioxino[5,4-b]pyrrole

(4aR,6S,7aS)-benzyl 6-hydroxymethyl-2,2-dimethyltetrahydro[1,3]dioxino[5,4-b]pyrrole-5(6H)-carboxylate