N-[(2R,4aR,6R,7R,8R,8aS)-6-Azido-2-phenyl-8-((2S,3S,4R,5R)-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide

Base Information

• Chemical Name: N-[(2R,4aR,6R,7R,8R,8aS)-6-Azido-2-phenyl-8-((2S,3S,4R,5R)-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide
• CAS No.: 397865-60-0
• Molecular Formula: C₄₁H₄₄N₄O₉
• Molecular Weight: 736.822
• Mol file: 397865-60-0.mol

Synonyms:N-[(2R,4aR,6R,7R,8R,8aS)-6-Azido-2-phenyl-8-((2S,3S,4R,5R)-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide

Chemical Property of N-[(2R,4aR,6R,7R,8R,8aS)-6-Azido-2-phenyl-8-((2S,3S,4R,5R)-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[(2R,4aR,6R,7R,8R,8aS)-6-Azido-2-phenyl-8-((2S,3S,4R,5R)-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide

There total 3 articles about N-[(2R,4aR,6R,7R,8R,8aS)-6-Azido-2-phenyl-8-((2S,3S,4R,5R)-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-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: 57.0%

4,6-O-benzylidene-2-acetamido-2-deoxy-β-D-glucopyranosylazide (168397-51-1) + ethyl 2,3,4-tri-O-benzyl-1-thio-α,β-D-arabinopyranoside (397865-59-7) → N-[(2R,4aR,6R,7R,8R,8aS)-6-Azido-2-phenyl-8-((2S,3S,4R,5R)-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide (397865-60-0)

Guidance literature:

With tetrabutylammomium bromide; copper(ll) bromide; In dichloromethane; N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1002/1521-3773(20011015)40:20<3836::AID-ANIE3836>3.0.CO;2-5

Reference yield:

(3S,4R,5R)-tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (108646-05-5) → N-[(2R,4aR,6R,7R,8R,8aS)-6-Azido-2-phenyl-8-((2S,3S,4R,5R)-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide (397865-60-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 49 percent / BF₃*Et₂O / CH₂Cl₂ / -15 °C

2: 88 percent / NaH / dimethylformamide / 0 °C

3: 57 percent / CuBr₂; Bu₄NBr / CH₂Cl₂; dimethylformamide / 20 °C

With boron trifluoride diethyl etherate; tetrabutylammomium bromide; sodium hydride; copper(ll) bromide; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/1521-3773(20011015)40:20<3836::AID-ANIE3836>3.0.CO;2-5

Reference yield:

ethylthio-tetra-O-acetyl-α,β-D-arabinopyranoside (397865-58-6) → N-[(2R,4aR,6R,7R,8R,8aS)-6-Azido-2-phenyl-8-((2S,3S,4R,5R)-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide (397865-60-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / NaH / dimethylformamide / 0 °C

2: 57 percent / CuBr₂; Bu₄NBr / CH₂Cl₂; dimethylformamide / 20 °C

With tetrabutylammomium bromide; sodium hydride; copper(ll) bromide; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/1521-3773(20011015)40:20<3836::AID-ANIE3836>3.0.CO;2-5

upstream raw materials:

4,6-O-benzylidene-2-acetamido-2-deoxy-β-D-glucopyranosylazide

ethyl 2,3,4-tri-O-benzyl-1-thio-α,β-D-arabinopyranoside

(3S,4R,5R)-tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate

ethylthio-tetra-O-acetyl-α,β-D-arabinopyranoside

Downstream raw materials:

Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-2-[(2R,3S,4R,5R,6R)-5-acetylamino-6-azido-2-benzyloxymethyl-4-((2S,3S,4R,5R)-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yloxy]-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester

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

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