(2S,3R,4S,5R,6R)-2-[2-((2R,3R,4R,5S,6R)-3-Azido-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl)-4-nitro-phenoxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

Base Information

Chemical Name:(2S,3R,4S,5R,6R)-2-[2-((2R,3R,4R,5S,6R)-3-Azido-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl)-4-nitro-phenoxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol
CAS No.:495400-37-8
Molecular Formula:C₁₉H₂₆N₄O₁₃
Molecular Weight:518.434
Hs Code.:

(2S,3R,4S,5R,6R)-2-[2-((2R,3R,4R,5S,6R)-3-Azido-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl)-4-nitro-phenoxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

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Chemical Property of (2S,3R,4S,5R,6R)-2-[2-((2R,3R,4R,5S,6R)-3-Azido-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl)-4-nitro-phenoxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

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Technology Process of (2S,3R,4S,5R,6R)-2-[2-((2R,3R,4R,5S,6R)-3-Azido-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl)-4-nitro-phenoxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

There total 5 articles about (2S,3R,4S,5R,6R)-2-[2-((2R,3R,4R,5S,6R)-3-Azido-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl)-4-nitro-phenoxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol 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: 53.0%

: (2S,3R,4S,5R,6R)-2-[2-((2R,3R,4R,5S,6R)-3-Amino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl)-4-nitro-phenoxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

: 495400-37-8
(2S,3R,4S,5R,6R)-2-[2-((2R,3R,4R,5S,6R)-3-Azido-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl)-4-nitro-phenoxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

Guidance literature:: With copper(I) sulfate; triflic azide; potassium carbonate; In methanol; dichloromethane; water;
DOI:10.1139/v02-156

Reference yield:

: 10022-13-6
1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose

: 495400-37-8
(2S,3R,4S,5R,6R)-2-[2-((2R,3R,4R,5S,6R)-3-Azido-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl)-4-nitro-phenoxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

Guidance literature:: Multi-step reaction with 4 steps

1: 84 percent / BF₃*OEt₂ / CH₂Cl₂ / 1 h / 20 °C

2: 70 percent / BF₃*OEt₂ / CH₂Cl₂ / 1 h / 20 °C

3: hydrazine hydrate / ethanol / 3 h / 90 °C

4: 53 percent / trifluoromethanesulfonyl azide; Cu₂SO₄; K₂CO₃ / H₂O; methanol; CH₂Cl₂

With copper(I) sulfate; triflic azide; boron trifluoride diethyl etherate; potassium carbonate; hydrazine hydrate; In methanol; ethanol; dichloromethane; water;
DOI:10.1139/v02-156

Reference yield:

: 39224-61-8
2-hydroxy-5-nitrobenzyl alcohol

: 495400-37-8
(2S,3R,4S,5R,6R)-2-[2-((2R,3R,4R,5S,6R)-3-Azido-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl)-4-nitro-phenoxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

Guidance literature:: Multi-step reaction with 4 steps

1: 84 percent / BF₃*OEt₂ / CH₂Cl₂ / 1 h / 20 °C

2: 70 percent / BF₃*OEt₂ / CH₂Cl₂ / 1 h / 20 °C

3: hydrazine hydrate / ethanol / 3 h / 90 °C

4: 53 percent / trifluoromethanesulfonyl azide; Cu₂SO₄; K₂CO₃ / H₂O; methanol; CH₂Cl₂

With copper(I) sulfate; triflic azide; boron trifluoride diethyl etherate; potassium carbonate; hydrazine hydrate; In methanol; ethanol; dichloromethane; water;
DOI:10.1139/v02-156