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

Base Information

Chemical Name: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
CAS No.:397865-61-1
Molecular Formula:C₄₁H₄₆N₄O₉
Molecular Weight:738.838
Hs Code.:

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

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 4 articles about 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 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: 68.0%

: 397865-60-0
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

: 397865-61-1
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

Guidance literature:: With hydrogenchloride; sodium cyanoborohydride; In tetrahydrofuran; diethyl ether; at 0 ℃;
DOI:10.1002/1521-3773(20011015)40:20<3836::AID-ANIE3836>3.0.CO;2-5

Reference yield:

: 108646-05-5
(3S,4R,5R)-tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate

: 397865-61-1
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

Guidance literature:: Multi-step reaction with 4 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

With hydrogenchloride; boron trifluoride diethyl etherate; tetrabutylammomium bromide; sodium hydride; sodium cyanoborohydride; copper(ll) bromide; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/1521-3773(20011015)40:20<3836::AID-ANIE3836>3.0.CO;2-5

Reference yield:

: 397865-58-6
ethylthio-tetra-O-acetyl-α,β-D-arabinopyranoside

: 397865-61-1
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

Guidance literature:: Multi-step reaction with 3 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

With hydrogenchloride; tetrabutylammomium bromide; sodium hydride; sodium cyanoborohydride; copper(ll) bromide; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/1521-3773(20011015)40:20<3836::AID-ANIE3836>3.0.CO;2-5