{(2R,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-[5-nitro-2-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-benzyloxy]-tetrahydro-pyran-3-yl}-carbamic acid allyl ester

Base Information

• Chemical Name: {(2R,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-[5-nitro-2-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-benzyloxy]-tetrahydro-pyran-3-yl}-carbamic acid allyl ester
• CAS No.: 495400-34-5
• Molecular Formula: C₂₃H₃₂N₂O₁₅
• Molecular Weight: 576.511

Synonyms:

Chemical Property of {(2R,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-[5-nitro-2-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-benzyloxy]-tetrahydro-pyran-3-yl}-carbamic acid allyl ester

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Technology Process of {(2R,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-[5-nitro-2-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-benzyloxy]-tetrahydro-pyran-3-yl}-carbamic acid allyl ester

There total 5 articles about {(2R,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-[5-nitro-2-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-benzyloxy]-tetrahydro-pyran-3-yl}-carbamic acid allyl ester 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: 64.0%

Allyl chloroformate (2937-50-0) + (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 → {(2R,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-[5-nitro-2-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-benzyloxy]-tetrahydro-pyran-3-yl}-carbamic acid allyl ester (495400-34-5)

Guidance literature:

With sodium hydrogencarbonate; In 1,4-dioxane; water;

DOI:10.1139/v02-156

Reference yield:

1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose (10022-13-6) → {(2R,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-[5-nitro-2-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-benzyloxy]-tetrahydro-pyran-3-yl}-carbamic acid allyl ester (495400-34-5)

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: 64 percent / NaHCO₃ / H₂O; dioxane

With boron trifluoride diethyl etherate; sodium hydrogencarbonate; hydrazine hydrate; In 1,4-dioxane; ethanol; dichloromethane; water;

DOI:10.1139/v02-156

Reference yield:

2-hydroxy-5-nitrobenzyl alcohol (39224-61-8) → {(2R,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-[5-nitro-2-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-benzyloxy]-tetrahydro-pyran-3-yl}-carbamic acid allyl ester (495400-34-5)

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: 64 percent / NaHCO₃ / H₂O; dioxane

With boron trifluoride diethyl etherate; sodium hydrogencarbonate; hydrazine hydrate; In 1,4-dioxane; ethanol; dichloromethane; water;

DOI:10.1139/v02-156

upstream raw materials:

Allyl chloroformate

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

2-hydroxy-5-nitrobenzyl alcohol

Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-(2-hydroxy-5-nitro-benzyloxy)-tetrahydro-pyran-4-yl ester

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