(R)-2-{(2S,3R,4R,5S,6R)-3-Acetylamino-5-[(2S,3R,4S,5S,6R)-6-(acetylamino-methyl)-3,4,5-trihydroxy-tetrahydro-pyran-2-yloxy]-2-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy}-propionic acid

Base Information

Chemical Name:(R)-2-{(2S,3R,4R,5S,6R)-3-Acetylamino-5-[(2S,3R,4S,5S,6R)-6-(acetylamino-methyl)-3,4,5-trihydroxy-tetrahydro-pyran-2-yloxy]-2-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy}-propionic acid
CAS No.:83116-27-2
Molecular Formula:C₂₆H₃₈N₂O₁₃
Molecular Weight:586.593
Hs Code.:

(R)-2-{(2S,3R,4R,5S,6R)-3-Acetylamino-5-[(2S,3R,4S,5S,6R)-6-(acetylamino-methyl)-3,4,5-trihydroxy-tetrahydro-pyran-2-yloxy]-2-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy}-propionic acid

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Chemical Property of (R)-2-{(2S,3R,4R,5S,6R)-3-Acetylamino-5-[(2S,3R,4S,5S,6R)-6-(acetylamino-methyl)-3,4,5-trihydroxy-tetrahydro-pyran-2-yloxy]-2-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy}-propionic acid

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Technology Process of (R)-2-{(2S,3R,4R,5S,6R)-3-Acetylamino-5-[(2S,3R,4S,5S,6R)-6-(acetylamino-methyl)-3,4,5-trihydroxy-tetrahydro-pyran-2-yloxy]-2-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy}-propionic acid

There total 9 articles about (R)-2-{(2S,3R,4R,5S,6R)-3-Acetylamino-5-[(2S,3R,4S,5S,6R)-6-(acetylamino-methyl)-3,4,5-trihydroxy-tetrahydro-pyran-2-yloxy]-2-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy}-propionic acid 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:

: 66530-19-6
(R)-2-[(2S,3R,4R,5S,6R)-3-Acetylamino-2-benzyloxy-6-hydroxymethyl-5-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-propionic acid methyl ester

: 83116-27-2
(R)-2-{(2S,3R,4R,5S,6R)-3-Acetylamino-5-[(2S,3R,4S,5S,6R)-6-(acetylamino-methyl)-3,4,5-trihydroxy-tetrahydro-pyran-2-yloxy]-2-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy}-propionic acid

Guidance literature:: Multi-step reaction with 9 steps

1: p-TsOH*H₂O / dimethylformamide / 2 h / 50 °C

2: pyridine

3: 60percent acetic acid / H₂O / 1 h / 50 °C

4: 310 mg / pyridine / 5 h / -25 °C

5: pyridine

6: 208 mg / sodium azide / dimethylformamide / 6 h / 60 °C

7: 1.) H₂ / 1.) 10percent Pd-C / 1.) methanol, room temperature, 2 h; 2.) methanol, 2 h

8: 99 mg / sodium methoxide / methanol / 0.05 h / Ambient temperature

9: 0.1 M aq. potassium hydroxide / dioxane; H₂O / 0.17 h / Ambient temperature

With pyridine; potassium hydroxide; sodium azide; hydrogen; sodium methylate; toluene-4-sulfonic acid; acetic acid; palladium on activated charcoal; In 1,4-dioxane; methanol; water; N,N-dimethyl-formamide;
DOI:10.1016/S0008-6215(00)82587-2

Reference yield:

: (R)-2-[(2S,3R,4R,5S,6R)-3-Acetylamino-2-benzyloxy-5-((4aR,6S,7R,8R,8aS)-7,8-dihydroxy-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-6-hydroxymethyl-tetrahydro-pyran-4-yloxy]-propionic acid methyl ester

: 83116-27-2
(R)-2-{(2S,3R,4R,5S,6R)-3-Acetylamino-5-[(2S,3R,4S,5S,6R)-6-(acetylamino-methyl)-3,4,5-trihydroxy-tetrahydro-pyran-2-yloxy]-2-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy}-propionic acid

Guidance literature:: Multi-step reaction with 8 steps

1: pyridine

2: 60percent acetic acid / H₂O / 1 h / 50 °C

3: 310 mg / pyridine / 5 h / -25 °C

4: pyridine

5: 208 mg / sodium azide / dimethylformamide / 6 h / 60 °C

6: 1.) H₂ / 1.) 10percent Pd-C / 1.) methanol, room temperature, 2 h; 2.) methanol, 2 h

7: 99 mg / sodium methoxide / methanol / 0.05 h / Ambient temperature

8: 0.1 M aq. potassium hydroxide / dioxane; H₂O / 0.17 h / Ambient temperature

With pyridine; potassium hydroxide; sodium azide; hydrogen; sodium methylate; acetic acid; palladium on activated charcoal; In 1,4-dioxane; methanol; water; N,N-dimethyl-formamide;
DOI:10.1016/S0008-6215(00)82587-2

Reference yield:

: C₄₉H₅₃NO₁₆

: 83116-27-2
(R)-2-{(2S,3R,4R,5S,6R)-3-Acetylamino-5-[(2S,3R,4S,5S,6R)-6-(acetylamino-methyl)-3,4,5-trihydroxy-tetrahydro-pyran-2-yloxy]-2-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy}-propionic acid

Guidance literature:: Multi-step reaction with 7 steps

1: 60percent acetic acid / H₂O / 1 h / 50 °C

2: 310 mg / pyridine / 5 h / -25 °C

3: pyridine

4: 208 mg / sodium azide / dimethylformamide / 6 h / 60 °C

5: 1.) H₂ / 1.) 10percent Pd-C / 1.) methanol, room temperature, 2 h; 2.) methanol, 2 h

6: 99 mg / sodium methoxide / methanol / 0.05 h / Ambient temperature

7: 0.1 M aq. potassium hydroxide / dioxane; H₂O / 0.17 h / Ambient temperature

With pyridine; potassium hydroxide; sodium azide; hydrogen; sodium methylate; acetic acid; palladium on activated charcoal; In 1,4-dioxane; methanol; water; N,N-dimethyl-formamide;
DOI:10.1016/S0008-6215(00)82587-2