(E)-3-[(2R,3R,4S,5R,6R)-6-((2R,3R,4S,5R,6R)-6-Azidomethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yl]-N-octyl-acrylamide

Base Information

• Chemical Name: (E)-3-[(2R,3R,4S,5R,6R)-6-((2R,3R,4S,5R,6R)-6-Azidomethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yl]-N-octyl-acrylamide
• CAS No.: 827026-15-3
• Molecular Formula: C₆₄H₇₄N₄O₁₀
• Molecular Weight: 1059.31
• Mol file: 827026-15-3.mol

Synonyms:(E)-3-[(2R,3R,4S,5R,6R)-6-((2R,3R,4S,5R,6R)-6-Azidomethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yl]-N-octyl-acrylamide

Chemical Property of (E)-3-[(2R,3R,4S,5R,6R)-6-((2R,3R,4S,5R,6R)-6-Azidomethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yl]-N-octyl-acrylamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-3-[(2R,3R,4S,5R,6R)-6-((2R,3R,4S,5R,6R)-6-Azidomethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yl]-N-octyl-acrylamide

There total 7 articles about (E)-3-[(2R,3R,4S,5R,6R)-6-((2R,3R,4S,5R,6R)-6-Azidomethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yl]-N-octyl-acrylamide 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: 45.0%

(E)-3-[(2R,3R,4S,5R,6R)-6-((2R,3R,4S,5R,6R)-6-Azidomethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yl]-acrylic acid methyl ester (827026-14-2) + n-Octylamine (111-86-4) → (E)-3-[(2R,3R,4S,5R,6R)-6-((2R,3R,4S,5R,6R)-6-Azidomethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yl]-N-octyl-acrylamide (827026-15-3)

Guidance literature:

With trimethylaluminum; In dichloromethane; toluene; at 20 ℃;

DOI:10.1016/j.bmc.2004.09.033

Reference yield:

(2S,3S,4S,5R,6R)-6-((2R,3R,4S,5R,6R)-6-Azidomethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-carbaldehyde → (E)-3-[(2R,3R,4S,5R,6R)-6-((2R,3R,4S,5R,6R)-6-Azidomethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yl]-N-octyl-acrylamide (827026-15-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride / tetrahydrofuran / 1 h

1.2: 0.16 g / tetrahydrofuran / 12 h

2.1: 45 percent / AlMe₃ / CH₂Cl₂; toluene / 20 °C

With trimethylaluminum; sodium hydride; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1016/j.bmc.2004.09.033

Reference yield:

6'-azido-2,2',3,3',4,4'-hexa-O-benzyl-6'-deoxy-α-D-trehalose (827026-13-1) → (E)-3-[(2R,3R,4S,5R,6R)-6-((2R,3R,4S,5R,6R)-6-Azidomethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yl]-N-octyl-acrylamide (827026-15-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: dimethylsulfoxide; oxalyl chloride; diisopropylethylamine / CH₂Cl₂ / -65 - 0 °C

2.1: sodium hydride / tetrahydrofuran / 1 h

2.2: 0.16 g / tetrahydrofuran / 12 h

3.1: 45 percent / AlMe₃ / CH₂Cl₂; toluene / 20 °C

With oxalyl dichloride; trimethylaluminum; sodium hydride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; toluene; 1.1: Swern oxidation;

DOI:10.1016/j.bmc.2004.09.033

upstream raw materials:

(E)-3-[(2R,3R,4S,5R,6R)-6-((2R,3R,4S,5R,6R)-6-Azidomethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yl]-acrylic acid methyl ester

n-Octylamine

6'-azido-2,2',3,3',4,4'-hexa-O-benzyl-6'-deoxy-α-D-trehalose

6-azido-2,2',3,3',4,4',6'-hepta-O-benzyl-6-deoxy-α,α'-trehalose