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

Base Information

• Chemical Name: 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
• CAS No.: 397865-63-3
• Molecular Formula: C₅₄H₆₂N₄O₁₄
• Molecular Weight: 991.105

Synonyms: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

Chemical Property of 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

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Technology Process of 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

There total 6 articles about 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 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: 93.0%

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 (397865-62-2) → 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 (397865-63-3)

Guidance literature:

With sodium methylate; In methanol;

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,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 (397865-63-3)

Guidance literature:

Multi-step reaction with 6 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

4: 68 percent / NaCNBH₃; HCl / tetrahydrofuran; diethyl ether / 0 °C

5: 49 percent / TMSOTf / CH₂Cl₂ / 48 h / -15 °C

6: 93 percent / MeONa / methanol

With hydrogenchloride; trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; tetrabutylammomium bromide; sodium methylate; sodium hydride; sodium cyanoborohydride; copper(ll) bromide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 6: Zemplen-transesterification;

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,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 (397865-63-3)

Guidance literature:

Multi-step reaction with 5 steps

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

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

3: 68 percent / NaCNBH₃; HCl / tetrahydrofuran; diethyl ether / 0 °C

4: 49 percent / TMSOTf / CH₂Cl₂ / 48 h / -15 °C

5: 93 percent / MeONa / methanol

With hydrogenchloride; trimethylsilyl trifluoromethanesulfonate; tetrabutylammomium bromide; sodium methylate; sodium hydride; sodium cyanoborohydride; copper(ll) bromide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 5: Zemplen-transesterification;

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

upstream 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

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

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

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

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