N-[(2R,3R,4R,5S,6R)-5-((2S,3R,4S,5R,6R)-4-Azido-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-yl]-acetamide

Base Information

• Chemical Name: N-[(2R,3R,4R,5S,6R)-5-((2S,3R,4S,5R,6R)-4-Azido-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-yl]-acetamide
• CAS No.: 172950-34-4
• Molecular Formula: C₂₉H₃₈N₄O₁₀
• Molecular Weight: 602.642
• Mol file: 172950-34-4.mol

Synonyms:

Chemical Property of N-[(2R,3R,4R,5S,6R)-5-((2S,3R,4S,5R,6R)-4-Azido-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-yl]-acetamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[(2R,3R,4R,5S,6R)-5-((2S,3R,4S,5R,6R)-4-Azido-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-yl]-acetamide

There total 4 articles about N-[(2R,3R,4R,5S,6R)-5-((2S,3R,4S,5R,6R)-4-Azido-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-yl]-acetamide 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:

methyl 3,6-di-O-benzyl-2-deoxy-2-N-phthalimido-β-D-glucopyranoside (97242-79-0) → N-[(2R,3R,4R,5S,6R)-5-((2S,3R,4S,5R,6R)-4-Azido-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-yl]-acetamide (172950-34-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 82 percent / silver triflate, molecular sieves 4 A / CH₂Cl₂ / 1 h / -40 - 20 °C

2: ethylenediamine, butanol / 70 °C

3: methanol / 2 h / Ambient temperature

With 4 A molecular sieve; silver trifluoromethanesulfonate; ethylenediamine; butan-1-ol; In methanol; dichloromethane;

DOI:10.1016/0008-6215(95)00165-P

Reference yield:

2,4,6-tri-O-acetyl-3-azido-3-deoxy-β-D-galactopyranosyl bromide (155301-09-0) → N-[(2R,3R,4R,5S,6R)-5-((2S,3R,4S,5R,6R)-4-Azido-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-yl]-acetamide (172950-34-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 82 percent / silver triflate, molecular sieves 4 A / CH₂Cl₂ / 1 h / -40 - 20 °C

2: ethylenediamine, butanol / 70 °C

3: methanol / 2 h / Ambient temperature

With 4 A molecular sieve; silver trifluoromethanesulfonate; ethylenediamine; butan-1-ol; In methanol; dichloromethane;

DOI:10.1016/0008-6215(95)00165-P

Reference yield:

methyl 2,4,6-tri-O-acetyl-3-azido-3-deoxy-β-D-galactopyranosyl-(1[*]4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (172950-32-2) → N-[(2R,3R,4R,5S,6R)-5-((2S,3R,4S,5R,6R)-4-Azido-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-yl]-acetamide (172950-34-4)

Guidance literature:

Multi-step reaction with 2 steps

1: ethylenediamine, butanol / 70 °C

2: methanol / 2 h / Ambient temperature

With ethylenediamine; butan-1-ol; In methanol;

DOI:10.1016/0008-6215(95)00165-P

upstream raw materials:

acetic anhydride

(2S,3R,4S,5R,6R)-2-((2R,3S,4R,5R,6R)-5-Amino-4-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-4-azido-6-hydroxymethyl-tetrahydro-pyran-3,5-diol

methyl 3,6-di-O-benzyl-2-deoxy-2-N-phthalimido-β-D-glucopyranoside

2,4,6-tri-O-acetyl-3-azido-3-deoxy-β-D-galactopyranosyl bromide